bluuebunny/crossref_metadata_2025 huggingface dataset:
Synthesis of C19 steroid monosulphates labelled with deuterium at specific positions
Authors: Rudqvist Ulf
Published: October 2006

Synthesis of C19 steroid monosulphates labelled with deuterium is reported. Deuterium was introduced either at hydroxylated carbons or in methylene groups, in order to permit use of the steroids in studies of intermolecular hydrogen transfer in vivo. Methylene groups were deuterated by equilibration of carbonyl α‐hydrogens with deuterium oxide. Deuterium at hydroxylated carbons was introduced by metal deuteride reduction. The sulphate group was introduced in the final step of a reaction sequence or, in some cases, in the step preceding the final one followed by removal of an acetate group.
Synthesis of [α‐14C]‐benzylguanidine
Authors: Inbasekaran Muthiah N. , Mangner Thomas J. , Wieland Donald M.
Published: October 2006

[α‐14C]‐benzylguanidine (1) having a specific activity of 14 mCi/mmol was synthesized in 55% yield (isolated) by reacting [α‐14C]‐benzylamine hydrochloride and cyanamide in 1‐butanol.
Preparation of specifically‐labelled buspirone ‐14C and buspirone ‐ 15N2
Authors: Covington R. R. , New J. S. , Yevich J. P. , Temple D. L.
Published: October 2006

Buspirone 1 is a novel, clinically effective anxiolytic agent which is devoid of the sedative, anticonvulsant or muscle relaxant properties normally associated with the benzodiazepines. Buspirone labelled with both radioactive (14C) and stable (15N) isotopes was required in order to investigate the metabolism of the compound. The synthesis of both labelled compounds beginning with either urea ‐ 14C or urea ‐ 15N2 is described.
Synthesis of hexadeuterated diethylstilbestrol ([1,1,1,6,6,6‐d6]‐E‐3,4‐di‐(4‐hydroxyphenyl)‐hex‐3‐ene)
Authors: Zomer Gijsbert , Derks Henk J. G. M. , Wynberg Hans
Published: October 2006

[1,1,1,6,6,6‐d6]‐E‐3,4‐di‐(4‐hydroxyphenyl)‐hex‐3‐ene was synthesized from [1,1,1‐d3]‐4‐methoxypropiophenone by reductive coupling. The preparation of [1,1,1‐d3]‐4‐methoxypropiophenone involved reaction of p‐anisoylchloride with perdeuterated diethyl‐cadmium followed by back‐exchange of the alpha protons.
The preparation of [15N]‐ and [1‐13C]‐2‐naphthylamine and their conversions into [15N, 15N′]‐ and [1,1′‐13C2]‐2,2′‐azonaphthalene
Authors: Gruszecka Ewa , Shine Henry J.
Published: October 2006

Specifically labelled [15N]‐2‐naphthylamine and [1‐13C]‐2‐naphthylamine have been synthesized with approx. 99% label abundance. The correspondingly highly‐enriched, doubly‐labelled 2,2′‐azonaphthalenes have been made.
Synthesis of 14C labelled metalaxyl and furalaxyl
Authors: Westcott Neil D. , Reichle Randy A.
Published: October 2006

The syntheses of the 14C labelled fungicides, metalaxyl and furalaxyl, are described. Sodium 2‐[14C]‐propionate was brominated at C‐2 and esterified with diazomethane to produce methyl 2‐bromo‐propionate. This bromopropionate was reacted with 2,6‐dimethyl‐aniline to produce methyl N‐(2,6‐xylyl)‐DL‐alaninate which was acylated with either methoxyacetyl chloride or 2‐furoyl chloride to produce 14C labelled metalaxyl and furalaxyl respectively.
Synthesis of tritiated cromolyn diethyl ester
Authors: Wyrick Steven D. , Ranga V.
Published: October 2006

We report here the synthesis of tritiated cromolyn diethyl ester of high specific activity and acceptable stability for use in in vitro and in vivo models of experimental asthma in the guinea pig. Preparation of an aryl brominated precursor, 1,3‐bis‐(2‐acetyl‐3‐hydroxy −6‐bromophenoxy)‐2‐propanol, followed by catalytic debromination with tritium gas and two subsequent synthetic steps atforded tritiated cromolyn diethyl ester with a specific activity of 135 mCi/mg (71 Ci/mmol).
Regioselective deuterium labelling of aromatic acids, amides and amines using group VIII metal catalysts
Authors: Lockley W J S
Published: October 2006

Ortho‐deuterated arylcarboxylic acids and their sodium salts may be prepared with high regioselectivity by isotopic exchange with deuterium oxide in the presence of a range of commercially available group VIII metal complexes. When rhodium trichloride trihydrate is employed a range of arylcarboxamides and arylmethanamines are also selectively labelled at the ortho‐positions.
Labeled bile acids II: Methyl 3β‐hydroxychol‐5‐en‐24‐oate, labeled with 13C and/or 2H
Authors: Byon Chang Yon , Gut Marcel , Lai Chee Kong
Published: October 2006

The incorporation of 13C, and/or 2H2, into methyl 3β‐hydroxychol‐5‐en‐24‐oate to give products with an abundance of the isotopic label at a specific position, useful for metabolism studies, has been accomplished.
Synthesis of 14C‐labelled methylazoxymethanol acetate of high specific activity
Authors: Cazer Frederick D. , Barnela Satish B. , Kumar Kultar S. , Kamat Prabhakar L. , Milo George E. , Witiak Donald T.
Published: October 2006

The micro‐scale synthesis of 14C‐labelled methylazoxymethanol acetate (14C‐MAM‐acetate) having a specific activity of 110 mCi/mmol was accomplished in 25% yield from N,N′‐[methyl‐14C] ‐dimethylhydrazine with a specific activity of 112.5mCi/mmol.
Tritium labeling of potential lipophilic myelin probes
Authors: Ehrenkaufer R. L. E. , Agranoff B. W. , Bieszki J. , Frey K. , Hays S. , Jewett D.
Published: October 2006

Two potential lipophilic myelin imaging agents (1,1,2,2‐tetrafluoro‐1,2‐diphenylethane and 1‐fluoroadamantane) were tritium labeled. The most effective method employed the microwave discharge activation of tritium gas technique and resulted in specific activities of 177 mCi/mmol for 1,1,2,2‐tetrafluoro‐1,2‐diphenylethane and 593 mCi/mmol for 1‐fluoroadamantane. Using this tritiation method significant amounts of tritium‐for‐fluorine substitution was also observed in the labeling of 1‐fluoroadamatane, resulting in nearly equivalent amounts of tritiated adamantane and fluoroadamantane.
Synthesis of (S)‐Nτ‐[D3] methylhistidine
Authors: Yuan Sun‐Shine , Ajami Alfred M.
Published: October 2006

(S)‐Histidine methyl ester was converted on a 20 g scale to its Nα, Nπ‐cyclic urea by treatment with carbonyl diimidazole. The Nτ position was alkylated with [D3]‐methyl iodide and the product was hydrolyzed to give isomerically and isotopically pure Nτ‐[D3] methylhistidine, without significant loss of optical activity.
Stereospecific synthesis of adenosine cyclic 3′,5′‐RP‐ and SP‐phosphoro‐[35S]thioates
Authors: Baraniak Janina , Reimschüssel Wtadystaw , Rudziński Juliusz , Stec Wojciech J.
Published: October 2006

Stereospecific reaction of both diastereoisomers of O2′,N6,N6‐tribenzoyladenosine cyclic 3′,5′‐phosphoranilidates (1) with sodium hydride and carbon [35S]disulphide gave, after removal of the protective groups, the desired RP — and SP‐diastereoisomers of [35S]cAMPS (2).
Methodes de Synthese de l'Acide Agarique Racemique Marque au 14C (acide α‐cetyl citrique (carboxyle‐1 14C) OU acide hydroxy‐2 nonadecanetricarboxylique‐1,2 (carboxyle 14CO)‐3)
Authors: Lellouche J. P. , Beaucourt J. P. , Pichat L.
Published: October 2006

Racemic [3‐carboxyl 14C] agaric acid triethyl ester was prepared in low yield by treatment of ethyl 2‐ethoxalyl octadecanoate 2 with either ethyl lithioacetate or ethyl bromoacetate, zinc and methyl borate. In another approach, lithio ethynyltrimethylsilane 6 was condensed with 2 to give 7 which, with dicyclohexylborane 8, gave the vinyl borane 9; the latter, by hydrogen peroxide oxidation followed by reaction of diazomethane gave the mixed ester 11 in low yield. [3‐carboxyl 14C] Agaric acid, specific activity 57 mCi/mmol, was obtained from 5 or 11 by saponification with lithium hydroxide in 1,2‐dimethoxyethane. The best overall yield from ethyl [1‐14C] stearate was 18%.
Synthesis of 14C‐labeled aminoglutethimide
Authors: Chaudhuri Naba K. , Servando Ofelia , Sung Ming‐Sang , Baumann Heinz
Published: October 2006

A new procedure has been developed for the synthesis of 14C‐labeled glutethimide with an improved yield from K14CN. In this procedure benzyl cyanide prepared from benzyl chloride and K14CN was almost quantitatively monoethylated by an ion‐pair extraction method using 50% excess of tetrabutylammonium hydroxide as the catalyst. Michael addition of methyl acrylate to monoethylbenzyl cyanide followed by hydrolysis with H2SO4 gave glutethimide which was then nitrated (HNO3 + H2SO4) and catalytically reduced to aminoglutethimide. The best result was obtained when the intermediate para‐nitroglutethimide was isolated in pure form by crystallization and then reduced in the presence of 10% Pd/C. When the nitration product (which was a mixture of isomers) was reduced without purification, isolation of pure p‐aminoglutethimide was more difficult and the yield was much lower.
Carbon‐14 and tritium labeled guanadrel sulfate
Authors: Hsi Richard S. P. , Johnson Tommy D. , Stolle Wayne T.
Published: October 2006

Carbon‐14 and tritium labeled (1,4‐dioxaspiro[4.5]dec‐2‐ylmethyl)guanidine sulfate, or guanadrel sulfate

Guanadrel sulfate is the USAN name for (1,4‐dioxaspiro[4.5]dec‐2‐ylmethyl) guanidine sulfate.

(1) were synthesized. The carbon‐14 label was incorporated into the dioxolane ring portion of guanadrel sulfate. The tritium labels were introduced into the cyclohexane ring portion of the molecule, at the beta and gamma positions with respect to the ketal linkage. The ketal resulting from the reaction of the original 2‐cyclohexen‐1‐one with 3‐phthalimido‐1,2‐propanedial contained a double bond in the β‐γ position rather than the α‐β postion of the original 2‐cyclohexen‐1‐one. This double bond shift provided a convenient method of introducing tritium into the 3‐and 4‐positions of cyclohexanone. Proof of the double bond position is discussed.
Synthesis of 4‐hydroxy[phenyl‐U‐14C]coumarin
Authors: Nadian Allan K.
Published: October 2006

Radiolabeled 4‐hydroxycoumarin was synthesized on a microscale by condensing [U‐14C]phenol and malonic acid in the presence of anhydrous zinc chloride and phosphorus oxychloride. The yield was 14% on a 0.5 mmol scale at a specific activity of 107 μCi/mmol.
Preparation of [18O]‐chlorocarbonylsulfenyl chloride
Authors: Mott Andrew W. , Eastep Steven J. , Słomczynska Urszula , Barany George
Published: October 2006

[18O]‐Chlorocarbonylsulfenyl chloride with an isotopic purity of 92% was prepared in three steps starting with the [18O]‐hydrolysis of 2‐ethyl‐1,3‐dioxolane to [18O]‐propanal, which was then converted to [18O]‐O‐1‐methylpropyl S‐methyl dithiocarbonate, which was then chlorinated to give the title compound. Distilled yields for the three steps were 57%, 49%, and 40% respectively.
Synthesis of dl‐glutamine‐2,5‐15N2
Authors: Lagna William M. , Callery Patrick S.
Published: October 2006

A two step synthesis of dl‐glutamine‐2,5‐15N2 is described. 2‐Oxapentanedioic acid was reacted with hydrazine sulfate‐15N2 to yield 6‐carboxy‐(2H)‐pyridazin‐3‐one‐1,2‐15N2, which was then reduced with hydrogen over 10% Pd/C catalyst to dl‐glutamine‐2,5‐15N2. Gas chromatography of the trimethylsilylated derivative of the labeled glutamine was used to establish purity. Mass spectra for dl‐glutamine‐15N2, dl‐glutamine and their intermediates, 6‐carboxy‐(2H)‐pyridazin‐3‐one‐1,2‐15N2 and 6‐carboxy‐(2H)‐pyridazin‐3‐one were consistent with assigned structures.
Synthesis of benzylic carbon‐14 labelled tulobuterol‐HCl
Authors: Ranade Vasant V.
Published: October 2006

Tulobuterol·HC1, a β‐adrenergic bronchodilating agent, was labelled with carbon‐14 in the benzylic position for metabolism studies.
1‐cyano‐1‐(6‐phenoxy‐2‐pyridinyl‐2, 6‐14C)methyl 3‐(2,2‐dichloroethenyl)‐2, 2‐dimethyl‐cyclopropanecarboxylate
Authors: McKendry L. H.
Published: October 2006

A 15.7 mCi sample of 99% radiochemically pure 1‐cyano‐1‐(6‐phenoxy‐2‐pyridinyl‐2,6‐14C)methyl 3‐(2,2‐dichloroethenyl)‐2,2‐dimethylcyclopropanecarboxylate with a specific activity of 21.3 mCi/mmole was prepared via a six step process from 2,6‐dichloropyridine‐2,6‐14C.
Synthesis of [carbonyl‐14C]‐ and (methoxy‐d3)‐labeled N‐[(2RS, 3RS)‐1‐benzyl‐2‐methyl‐3‐pyrrolidinyl] −5‐chloro‐2‐methoxy‐4‐(methylamino) benzamide (YM‐09151‐2). A new potent neuroleptic agent
Authors: Tamazawa Kazuharu , Arima Hideki
Published: October 2006

A new potent neuroleptic agent YM‐09151‐2, N‐[(2RS, 3RS)‐1‐benzyl‐2‐methyl‐3‐pyrrolidinyl]‐5‐chloro‐2‐methoxy‐4‐ (methylamino) benzamide (10c), was labeled with carbon‐14 and deuterium for biochemical studies such as metabolism and 14 pharmacokinetics. The synthesis of [carbonyl‐14C]YM‐09151‐2 (10a) from 4‐amino‐2‐hydroxy‐[carboxyl‐14C] benzoic acid (1a) in six stages is described. Overall radiochemical yield was 79.1% at a specific activity of 21.18 mCi/mmol. (Methoxy‐d3)YM‐09151‐2 (10b) was prepared from methyl 2‐(methoxy‐d3)‐4‐(N‐methyl‐N‐tosylamido) benzoate (5b) which was obtained by the reaction of methyl 2‐hydroxy‐4‐(N‐methyl‐N‐tosylamido) benzoate (4c) with iodomethane‐d3. Overall yield of 10b was 60.8% from iodomethane‐d3.
Synthesis of 5‐hydroxy‐[6‐14C]‐methyl‐2‐di‐n‐propylaminotetralin
Authors: Koble Dale L. , Fischer Lawrence J.
Published: October 2006

By an improved synthesis, 5‐hydroxy‐6‐methyl‐2‐di‐n‐propylaminotetralin (DK‐118), a dopamine agonist, has been obtained in only six steps and in greater than 10% overall yield. This new synthesis has been used for the preparation of 5‐hydroxy‐[6‐14C]‐methyl‐2‐di‐n‐propylaminotetralin (I) to be used in metabolic studies. The 14C‐radiolabel was introduced near the end of the synthesis by an ortho‐specific formylation procedure using 14C‐paraformaldehyde.
Labeled bile acids V: Deuterium and carbon‐13 labeled cholic, chenodeoxycholic and ursodeoxycholic acids
Authors: Lai Chee Kong , Byon Chang Yon , Gut Marcel , Mostowicz Danuta , Anderson Warren G.
Published: October 2006

This paper describes a general, simple and short procedure for the introduction of stable isotopes (deuterium and carbon‐13) to the side chain of bile acids. The bisnorcholyl aldehydes of cholic and chenodeoxycholic acids are key intermediates, while the isotope is introduced by the Wittig condensation of [1,2‐13C2]‐(carbethoxymethylene)triphenyl‐phosphorane.
Syntheses of piperidine and granatanine doubly isotopically substituted with carbon‐13
Authors: Barna Jennifer J. C. , Robinson Michael J. T.
Published: October 2006

Syntheses of (2,3‐13C2) piperidine and (1,2‐13C2) granatanine via (1,2‐13C2)‐glutaric acid have been achieved using a benzene ring as a potential carboxyl group.
Stable isotope labeled alpha‐ketoacids
Authors: Yuan Sun‐Shine , Ajami Alfred M.
Published: October 2006

Alkylation of diethyl oxalpropionate with [D3]methyl iodide followed by acid hydrolysis led to 3‐[D3]methyl‐2‐oxobutyric (α‐ketoisovaleric) acid. Alkylation of N‐t‐butylpropylimine with [D3]methyl iodide followed by hydrolysis gave 2‐[D3]methylpropanal. This was further alkylated with 2,2‐difluoro‐1‐tosyloxyvinyllithium and hydrolyzed to afford 4‐[D3]methyl‐2‐oxopentanoic (α‐ketoisocaproic) acid. Diazotization of [1‐13C]leucine ethyl ester with t‐butylnitrite followed by peracid oxidation and hydrolysis gave [1‐13C]4‐methyl‐2‐oxopentanoic acid. In each case, the α‐ketoacids were isolated as sodium salts.
A convenient preparation of 14C‐labelled 5H‐2,3‐benzodiazepines
Authors: Zólyomi G. , Láng T. , Körösi J. , Hámori T.
Published: October 2006

A convenient method for preparing 5H‐2,3‐benzodi‐azepines labelled with 14C was developed in which the corresponding phenylacetone derivatives were acylated by labelled aromatic carboxylic acid. In spite of the low yield, this method is advantageous in comparison the known ones because of the obtainable specific activity, which is a consequence of the few stages and simplicity of the synthesis.
Synthesis of [3H] porfiromycin
Authors: Swigor J. E. , Pittman K. A.
Published: October 2006

The synthesis of the title compound (1) is described. The reaction of a specific amount of [3H] methyl iodide under controlled conditions with naturally occurring mitomycin C produced [3H] porfiromycin with an overall yield of 61% and a radiochemical purity of 98%.
The synthesis of α‐methylstyrenes with 14C‐labelling in the side chain
Authors: Ali H. M. , Barson C. A. , Coe P. L.
Published: October 2006

α‐Methylstyrenes with all three side chain carbons specifically 14C‐labelled have been synthesised by Wittig reactions between the appropriately labelled acetophenones or methylene triphenylphosphoranes. The yields in all cases were good and any radiochemical impurities could be readily removed by distillation.
Synthesis of hydroxyl[13N]amine and binding of 13NH2OH to two transaminases
Authors: Kaseman Deborah S. , Cooper Arthur J. L. , Meister Alton , Gelbard Alan S. , Reiman Robert E.
Published: October 2006

NH2OH was labeled with a β+emitter (13N, t1/2 = 9 96 min.). Hydroxyl[13N]amine was synthesized from HSO and [13N]nitrite (produced via the 160(p,α)13N reaction by proton bombardment of H2O). The synthesis reactions are: magnified image Hydroxyl[13N]amine was purified by ion‐exchange chromatography on Dowex‐1 × 8 (AcO−) to remove unreacted 13NO and 13NO. Radiochemical yields of 50–90% were obtained in 25–30 min. The purity and specific activity of 13NH2 OH were determined by HPLC analysis and spectrophotometric assay. The binding of 13NH2 OH to pig heart glutamate‐pyruvate transaminase and to pig heart glutamate‐oxaloacetate transaminase was measured. This work demonstrates that quantitation of the binding of hydroxylamine (an active‐site directed enzyme inhibitor) labeled with a positron‐emitting isotope is technically feasible.
Preparation of [131I] iodinated nonoxynol‐9
Authors: Agha Bushra J. , Garbolas George A. , Wets Kathleen , Digenis George A.
Published: October 2006

A novel method for the radioiodination [131I] of the multicomponent non‐ionic surfactant nonoxynol‐9 (N‐9) is described. The extent of incorporation and distribution of the 131I‐label into the aromatic moiety of various ethoxymer units of N‐9 was determined utilizing a high pressure liquid chromatographic (HPLC) method.
Fast low temperature ultrasonic synthesis and injection ready preparation of carrier free 17‐I‐123‐heptadecanoic acid
Authors: Mertens John , Vanryckeghem Wim , Bossuyt Axel , Van Den Winkel Pierre , Vandendriessche René
Published: October 2006

17‐I‐123‐heptadecanoic acid is prepared carrier‐free from 17‐Br‐heptadecanoic acid in methyl ethyl ketone at 100°C. A quantitative labeling yield is obtained within 20 minutes using a 50 KHz ultrasonic bath. Sonication allows the presence of water up to 7.5% v/v. The pattern shown by the plot of the kinetic curves is typical of two consecutive reactions: the first being the dissociation of a radioactive side product, the second a I− for Br nucleophilic exchange. The pure carrier‐free radioiodinated fatty acid is obtained by HPLC separation and is used clinically in a sterile 6% human serum albumine solution. The quality control of the injection ready solution is based on the use of a RP18 Sep‐PakR cartridge.
Reduction of iminium ethers with sodium boro[3H] hydride. Preparation of tritium labelled clomiphene and nitromiphene (CI 628)
Authors: Ruenitz Peter C. , Bagley Jerome R.
Published: October 2006

The preparation of [3H]‐clomiphene and [3H]‐nitromiphene from amido precursors in a two‐step reaction sequence utilizing NaB H4 is described. The radiochemical yield and specific activity of the former are 34% and 16 mCi/mmol and those of the latter were 42% and 20 mCi/mmol, respectively. The method described is of micromolar scale designed for maintaining cost economy in the purchase of expensive radiolabelled reagents while yielding final products of sufficient radioactivity for in vitro and in vivo metabolism studies.
Synthesis of [14C]2‐pipecolinyl‐5‐amino‐4′‐chloro‐benzophenone (LF.1695)
Authors: Luu‐Duc C. , Béney C. , Le Bars D. , Charlon C. , Marsura A. , Bellamy F. , Ou K.
Published: October 2006

Two synthetic routes lead to [14C] LF.1695. The first one starts with labelled triphenyl methyl phosphonium iodide. This Wittig reagent reacts with benzyl piperidinone to afford benzylmethylidene piperidine 3. The reduction of 3 gives labelled pipecoline 4 which is condensed with an adduct affording an intermediate nitro compound 5. LF.1695 6 labelled at the methyl group is then obtained by catalytic reduction.

The second route uses labelled chloro‐nitro benzoic acid as starting material. The treatment of the corresponding acid chloride by Friedel‐Crafts reaction gives the chloro‐nitro‐chloro‐benzophenone 9 in good yield. Condensation of 9 with pipecoline according to the method described above gives an intermediate nitro compound 10 which is reduced to afford LF.1695 11 labelled at the carbonyl group.
Synthesis of carbon‐14 labeled capsaicin
Authors: Bodine Richard S. , Chien Ping‐Lu
Published: October 2006

The synthesis and purification of carbon‐14 labeled capsaicin are described.
Regioselective synthesis of unsymmetrical deuterium labelled hydrazines and azoxy compounds
Authors: Cooper Curt S. , Weinkam Robert J.
Published: October 2006

A method for the preparation of deuterium labelled unsymmetrical hydrazines was developed. This method was used to prepare l‐benzyl‐2‐methyl‐2H3‐hydrazine hydrobromide and l‐benzyl‐2H7‐2‐methylhydrazine hydrobromide, analogs of the cancer chemotheraputic agent procarbazine. These compounds were then used to prepare the corresponding labelled benzyl‐(ONN) and (NNO)‐azoxymethane isomers. A method was developed whereby the deuterium labelled azoxy isomers were separated by reversed phase semi‐preparative HPLC.
Synthesis of 4‐(2‐chlorophenyl)‐1, 6‐dihydro‐1, 3, 9‐trimethylimidazo[1, 2‐a]pyrazolo[4, 3‐f] [1, 4]diazepine‐9‐14C (CI‐918‐14C)
Authors: Hicks James L. , Huang C. C. , Goel Om P. , Butler Donald E.
Published: October 2006

4‐(2‐Chlorophenyl)‐1, 6‐dihydro‐1,3,9‐trimethylimidazo[1,2‐a]pyrazolo‐[4,3‐f] [1,4]diazepine‐9‐14C (CI‐918‐14C) was made starting with acetyl‐1‐14C chloride. An efficient synthesis of 1‐chloro‐2‐propanone‐2‐14C was developed as a precursor to 2‐methyl‐1,3‐dioxolane‐2‐14C‐2‐methanamine. The latter reacted with 4‐(2‐chlorophenyl)‐1,6‐dihydro‐1,3‐dimethylpyrazolo[3,4‐e] [1,4]diazepine‐7‐thione to yield 4‐(2‐chlorophenyl)‐1,6‐dihydro‐1, 3‐dimethyl‐N‐[(2‐methyl‐1,3‐dioxolan‐2‐yl‐2‐14C)methyl] pyrazolo[3,4‐e] [1,4]diazepin‐7‐amine. Hydrolysis and cyclization gave the title compound. The six‐step reaction sequence gave an overall radiochemical yield of 19%. The product had a specific activity of 8.31 mCi/mmol.
Synthesis of 14C‐anthralin
Authors: Brown C. , Eustache J. , Frideling J. P. , Shroot B.
Published: October 2006

1,8‐dihydroxy‐[10‐14C]9‐anthrone (anthralin) was synthesized in good yield starting from readily available 3‐methoxy‐2‐(2‐methoxybenzyl)‐benzoic acid (3).

14C was introduced via carboxylation of the Grignard derived from 3‐bromo‐2(2‐methoxybenzyl) anisole. This, in turn, was obtained from (3) by a Curtius and Sandmeyer reaction sequence.
Synthesis of N‐[2‐3H] acetyl‐D‐muramyl‐L‐alanyl‐D‐iso‐glutaminyl‐L‐alanyl‐2‐(1′,2′‐dipalmitoyl ‐sn‐glycero‐3′‐phosphoryl) ethylamide of high specific radioactivity
Authors: Brundish D. E. , Wade R.
Published: October 2006

The title compound (MTP‐cephalin) was synthesised with specific activity of 22 Ci mmol−1 and with radiochemical purity of 96–98% by a direct radiochemical synthesis using [3H] muramyl dipeptide. Several unsuccessful approaches to the target compound are documented.
Radiolabelling of the histamine liberating sesquiterpene lactone, thapsigargin
Authors: Br Christensen S. ØGger
Published: October 2006

Thapsigargin (1) selectively labelled in the butyrate moiety of the molecule was isolated after hydridocarbonyltris (triphenylphosphine) rhodium (I) catalyzed reduction of the product (5) obtained by reacting debutanoylthapsigargin (2) with 3‐butenoic anhydride. The use of tritium gas as a reducing agent afforded labelled thapsigargin with a specific activity of 78 Ci/mmol.
Synthese DU cyclopropylmethyl‐2 di(paramethoxyphenyl)‐5,6 oxo‐3 triazine‐1,2,4 (14C‐3) (ST 1118)
Authors: Bonnaud B. , Cousse H. , Noël J. P. , Pichat L. , Pitet G.
Published: October 2006

(14C) semicarbazide hydrochloride was obtained from (14C) urea and hydrazine hydrate. It was condensed with 1,2‐di‐ (4‐methoxy phenyl)‐ethane‐1,2‐dione giving rise to 5, 6‐di‐(4‐methoxyphenyl)‐3‐oxo‐(3‐14C)‐1,2,4‐triazine. The latter, after condensation with bromomethyl cyclopropane gave (3‐14C) ST 1118 : 2‐(cyclopropylmethyl)‐5,6‐di‐(4‐methoxyphenyl)‐3‐oxo‐(3‐14C)‐1,2,4‐ triazine. The overall yield based on urea was 37.2%. After silicagel column chromatography and crystallisation the radiochemical purity was 99.5% ‐ Specific activity : 5.8 mCi/mMole.
Synthesis of pyrilamine‐d6
Authors: Bird Ian , Shuker David E G
Published: October 2006

Pyrilamine‐d6 (N‐[(4‐methoxyphenyl)methyl]‐N′, N′‐di[2H3]methyl‐N‐2‐pyridinyl‐1,2‐ethanediamine) was synthesised from N‐2‐[(4‐methoxyphenyl)methyl]‐aminopyridine and 2‐(N,N‐di[2H3]methylamino)ethyl chloride in 83% yield. The alkyl chloride was prepared in 37% overall yield in a three step reaction from toluene‐4‐sulphondi [2H3]methylamide.
Convenient preparation of deuterated uracils and dihydrouracils
Authors: Hill Richard K. , Ledford N. Dale , Renbaum Louis A.
Published: October 2006

The reaction of [3‐2H1]propiolic acid with urea provides a simple route to [6‐2H1]uracil, and further exchange with DCl affords [5,6‐2H2]uracil. Reaction of the meso and d, 1‐isomers of [2,3‐2H2]succinamide with lead tetraacetate leads to the cis and trans isomers of [5,6‐2H2]5,6‐dihydrouracil.
Synthesis and unusual NMR spectra of 4,4′‐dinitro‐3,3′‐bifurazanyl‐4,4′‐13C
Authors: Coburn Michael D.
Published: October 2006

The synthesis of 4,4′‐dinitro‐3,3′‐bifurazanvl‐4,4′‐13C was accomplished starting with sodium cyanide‐13C and dichloroglyoxime. The carbon‐13 NMR spectrum of the product consists of a 1,1, l‐triplet and the nitrogen‐14 NMR spectrum contains a sharp doublet with the same coupling constant as the carbon‐13 triplet.
Tritium labelled (±)‐7‐chloro‐8‐hydroxy‐3‐methyl‐1‐phenyl‐2,3,4,5‐tetrahydro‐1H‐3‐benzazepine (SCH23390)
Authors: Wyrick Steven D. , Mailman Richard B.
Published: October 2006

The antipsychotic drug, SCH23390, once thought to be the first selective D1 dopamine antagonist, is now believed to possibly produce its profound antidopaminergic and antipsychotic effects via molecular sites that involve recognition characteristics similar to, or are a subpopulation of the D1 dopamine receptors. Tritium labelled SCH23390 has been prepared in our laboratory by palladium catalyezed reductive aryl debromination of a brominated precursor with carrier free tritium gas in THF. The product is labelled in the 9‐position of the benzazepine ring and a specific activity of 5.6 Ci/mmole was obtained.
Synthesis of 14C‐labelled milrinone
Authors: Duncan D. R. , Johnston D. , Andrews R. S.
Published: October 2006

A synthetic procedure for producing 14C‐labelled milrinone is described. The synthesis was achieved in two steps from 1‐(4‐pyridyl)propan‐2‐one utilising [2‐14C]cyanoacetamide as the source of the radiolabel. The overall chemical yield was 46% and the radiochemical yield 35%.
Synthesis of carbon‐14 labeled clomiphene
Authors: Rao P. Narasimha , Cessac James W.
Published: October 2006

Clomiphene, 2‐[4‐(2‐chloro‐1,2‐diphenylethenyl)phenoxy]‐N, N‐diethylethanamine, an antiestrogen, is a nonsteroidal triphenylethylene derivative. For the successful synthesis of carbon‐14 labeled clomiphene it is essential to have a free radical inhibitor in the reaction medium.
Preparation and purification of 125I‐labeled iodospiroperidol
Authors: Landvatter Scott W.
Published: October 2006

Iodine‐125 labeled spiroperidol has been synthesized by a simple, one‐step procedure starting from spiroperidol. This synthesis employs 125I‐ and H2O2 in buffered acetic acid. This pH dependent reaction affords iodospiroperidol in 40% radiochemical yield and a specific activity, after HPLC purification, of ca. 1900 Ci/mmol.
Synthesis of iodine‐125 labelled ω‐iodoundecyl cholesteryl ether
Authors: Kabalka George W. , Varma Rajender S. , Jinaraj Vadeparambil K. , Huang Leaf , Painter Susan K.
Published: October 2006

ω‐[125I]Iodoundecyl cholesteryl ether has been synthesized via a hydroboration‐iodination sequence. The syntheses can be used to prepare high specific activity (no‐carrier‐added) reagents.
Synthesis, 1H‐NMR and mass spectra of 2‐2H‐, 2,3‐2H2‐ and 2,2‐2H2‐labelled short chain carboxylic acids
Authors: Hine David G. , Ikeda Yasuyuki , Tanaka Kay
Published: October 2006

2‐2H, 2,3‐2H2 and 2,2‐2H2 ‐ short chain carboxylic acids were synthesized. Monodeuteration at the 2‐position of the carboxylic acids was achieved via decarboxylation of the corresponding carboxyldeuterated 2‐alkylmalonic acids. 2,3‐Dideuteration was achieved via catalytic deuteration of the corresponding 2,3‐ unsaturated carboxylic acids with sodium borodeuteride. 2,2‐Dideuteration was achieved via repeated base catalyzed exchange reactions of the carboxylate sodium salts in sodium deuteroxide/deuterium oxide solution. Proton nuclear magnetic resonance and mass spectra of the obtained products are presented.
Synthesis of (21‐3H3)‐pregnenolone
Authors: Prasad V. V. Kris , Franklin Steven O.
Published: October 2006

A simple procedure for the preparation of 21‐3H ‐ pregnenolone using pregnenolone as starting material is described. The procedure involved removal of the C‐21‐methyl group of the steroid and the side‐chain was reconstructed with 3H CH3MgI in two steps: a Grignard reaction followed by oxidation of the resulting alcohol. An overall yield of 71% was achieved.
75,77Br‐Nor‐zimelidine: Radiohalogenation of a complex molecule via a trimethylstannyl precursor
Authors: Kloster Gerd , Laufer Peter , Hanuš Jan
Published: October 2006

This communication describes the preparation of radiobrominated nor‐zimelidine (III), a potential tracer for the serotonin reuptake system of the brain, by a bromodemetallation reaction using a suitable trimethylstannyl precursor (II). (II) was prepared from NaSn (CH3)3 and nor‐zimelidine in low yield and thoroughly purified by preparative hplc. Bromodemetallation reaction using an equimolar amount of Br2 showed quantitative formation of nor‐zimelidine without any detectable side‐products. Radiobromination yields using n.c.a. 75,77Br at the 100 μCi level were 60 % with one hour preparation time including purification. Conditions were not optimized for large scale production of high specific activity (III) since the compound was withdrawn from the market by the producer during the course of this study.
Synthesis of 4‐fluoro‐4′‐trifluoromethylbenzophenone guanylhydrazone hydrochloride labeled with 14C
Authors: Wang Theodore S. T. , Fawwaz Rashid A.
Published: October 2006

Four steps were required to synthesize the title compound. This involved carboxylation, acid chloride formation, condensation, and hydrazone formation. The overall radiochemical yield was 12.5% amd the specific activity was 2.04 mCi/mmole. Because of the difficulty encountered in preparing the p‐fluorobenzal‐dehyde‐aldehyde‐14C, p‐fluorobenzoyl chloride‐carbonyl14C was used for the condensation reaction.
Synthesis of (β‐methyl3H‐6β‐iodopenicillanic acid
Authors: De Meester Fabien , Frère Jean‐Marie , Piette Jean‐Louis , Vanderhaeghe Hubert
Published: October 2006

A rapid and easy synthesis of tritium‐labelled β‐iodopenicillanate, an efficient inactivator of serine β‐lactamase, is described. This method involves only three reaction steps after the introduction of the label in the molecule with an overall yield of 16 %.
Radiobromination of the 1‐position of estradiol using no‐carrier‐added bromine‐77
Authors: Hylrides Mark D. , Buksa Patricia L. , Mettler Fred A. , Wilbur D. Scott
Published: October 2006

The target compound, 1‐([77Br]bromo)estradiol (1a), was prepared in three steps from 4‐aminoestradiol, 3‐methyl ether (2). Electrophilic bromination of 2 with in situ generated 77BrCl followed by deamination in the same reaction mixture gave 1‐([77Br]bromo)estradiol 3‐methyl ether (4a) in 59% radiochemical efficiency. Subsequent demethylation of 4a gave la in 92% radiochemical efficiency with an estimated specific activity of 300–600 Ci/mmol. An overall radiochemical yield of approximately 20% was obtained. Stability studies of la showed no decomposition over a three‐day period.
The preparation of H218O2 in aqueous solution
Authors: Sitter Andrew J. , Terner James
Published: October 2006

A method is described for the preparation of [18O]‐hydrogen peroxide in an aqueous solvent of natural isotopic abundance through the autoxidation of 2‐ethyl anthrahydroquinol with gaseous 18O2.
Synthesis of |24‐14C|‐23‐norcholanoic acid derivatives
Authors: Maier M. S. , Seldes A. M. , Gros E. G.
Published: October 2006

Syntheses of |24‐14C| 3β, 20ξ‐dihydroxy‐23‐norchol‐5‐enoic acid, |24‐14C| 3β, 20ξ‐dihydroxy‐23‐norcholanoic acid and |24‐14C| 20ξ‐hydroxy‐3‐oxo‐23‐norchol‐4‐enoic acid were accomplished by reaction of ethyl |1‐14C| bromoacetate, in Reformatsky conditions, with suitable 20‐keto‐pregnane derivatives. Dehydration of these products afforded |24‐14C| 3β‐hydroxy‐23‐norchola‐5, 20(22)E‐enoic acid and |24‐14C| 3‐oxo‐23‐norchola‐4, 20(22)E‐dienoic acid respectively. The products were characterized by spectroscopic (IR, 1H NMR, MS) methods.
13C‐Labelled benzo[a]pyrene and derivatives. An efficient pathway of labelling the 1‐, 2‐, and 3‐positions
Authors: Bodine Richard S. , Daub Guido H. , Vanderjagt David
Published: October 2006

A ten step synthesis of benzo [a]pyrene‐1‐13C, ‐2‐13C, or 3‐13C from 2,3,7,11b‐tetrahydrobenz[d, e] anthracen‐3(1h)‐one is described in which the initial step involves the condensation of this ketone with the lithium enolate of ethyl acetate. This completes our synthesis of the tweleve 13C labelled benzo[a]pyrenes.
Synthesis of [13N]cisplatin
Authors: Haber Martin T. , Cooper Arthur J. L. , Rosenspire Karen C. , Ginos James Z. , Rottenberg David A.
Published: October 2006

A method for the “carrier‐added” synthesis of [13N]cisplatin is described. Yields were ∼1–4 mCi from 20–40 mCi of [13N]ammonia with a total synthesis time of 19–28 minutes. The product was ∼96% radiochemically pure as judged by HPLC analysis and had a specific activity of ∼100 mCi/mmole in 1.0 ml of saline. [13N]Cisplatin was administered intraperitoneally to mice. Of the tissues investigated, concentration of label was highest in kidneys. At 10 min, considerable label in the blood, liver, and kidney was in a form other than cisplatin. However, no evidence was obtained that [13N]ammonia was released from [13N]cisplatin in vivo. [13N]Cisplatin may be used to assess drug delivery to primary and metastatic brain tumors in patients receiving intravenous or intraarterial cisplatin chemotherapy.
Preparation of 2‐chloro‐6‐(2‐furanylmethoxy)‐4‐trichloromethylpyridine‐2,6‐14C
Authors: McKendry L. H.
Published: October 2006

A 16.7 mCi sample of 99+% radiochemically pure 2‐chloro‐6‐(2‐furanylmethoxy)‐4‐trichloromethylpyridine‐2,6‐14C with a specific activity of 13.2 mCi/mmole was prepared from trimethyl citrate‐1,5‐14C in a 44% yield via a three‐step process.
Synthesis of 1‐amino‐2‐β‐(3‐ [2,6‐14C] piperidinome thylphenoxy) propylamino ‐1‐cyclobutene‐3,4‐dione hydrochloride
Authors: Swigor J. E. , Algieri A. A. , Standridge R. T. , Pittman K. A.
Published: October 2006

The synthesis of the title compound (6) is described. The condensation of 3‐aminopropanol with phthalic anhydride and subsequent treatment with phosphorous tribromide produced N‐[3‐bromopropyl] phthalimide. Acylation with 3‐hydroxybenzaldehyde, reduction with hydrogen over Raney nickel and subsequent treatment with thionyl chloride gave N‐[ 3‐(3‐chloromethylphenoxy) propyl ] phthalimide (2). Treatment with [2, 6 ‐ 14C] piperidine introduced the radiolabel (3). Deprotection of the amino group with hydrazine and treatment with 3‐methoxy‐4‐amino‐3‐cyclobutene‐1,2‐dione produced 1‐amino‐2‐ [3‐(3‐[ 2,6‐ 14C] piperidinome thylphenoxy) propylamino ]‐1‐cyclobutene‐3, 4‐dione (5). Treatment with hydrochloric acid yielded the title compound (6) in an overall chemical yield of 22%.
Synthesis of labelled ecdysone precursors: Part I‐tritium labelled (3H4‐22, 23,24,25)‐3β, 14α‐dihydroxy‐5β‐cholest‐7‐en‐6‐one
Authors: Haag T. , Hetru C. , Nakatani Y. , Luu B. , Pichat L. , Audinot M. , Meister M.
Published: October 2006

High specific activity tritiated 3β, 14α ‐dihydroxy‐5β‐cholest‐7‐en‐6‐one, has been prepared using a precursor which permits rapid and easy labelling. This compound is converted to ecdysone under in vitro conditions by insect prothoracic glands, a well known site of ecdysone biosynthesis.
[11C]Labeling of coenzyme Q10 and its tissue distribution
Authors: Takahashi T. , Ido T. , Iwata R. , Ishiwata K. , Hamamura K. , Kogure K.
Published: October 2006

[11C]Coenzyme Q10 was synthesized by O‐methylation of 3‐demethyl coenzyme Q10 with 11CH3I. We have produced 1–4 mCi of [11C]coenzyme Q10 with radiochemical yields of 6–16 % (based on trapping 11CH3I) in 35–50 min with radiochemical purities of >95%. The specific activity was 4–5 mCi/μMol at the end of [11C]‐coenzyme Q10 synthesis. The tissue distribution was investigated on mongolian gerbils after intravenous administration of [11C]‐coenzyme Q10 solubilized with polyoxyethylene hydrogenated caster oil (HCO‐60). The blood level of [11C]coenzyme Q10 was very high and its clearance was slow. The accumulations in the heart, kidney and liver were moderate and the accumulation in the brain was low in spite of its high lipophilicity.
Synthesis of [4′‐13C] pyridoxol
Authors: Velde V. W. Vande , Mackenzie N. E. , Scott A. I.
Published: October 2006

5‐Cyano‐3‐hydroxy‐2‐methylpyridine‐l‐oxide, after O‐methylation with dimethylsulfate, was reacted regiospecifically with sodium [13C] cyanide to give [4′‐13C] 4,5‐dicyano‐3‐hydroxy‐2‐methylpyridine. The latter compound was successively transformed to [4′‐13C] pyridoxol and [4′‐13C] pyridoxal phosphate.
Synthesis of [1‐14C‐carboxy]‐4‐benzoylbenzoic acid
Authors: Nakamaye Kay L. , Yount Ralph G.
Published: October 2006

[1‐14C‐Carboxy]‐4‐benzoylbenzoic acid has been prepared via a Grignard reaction with 14CO2. 4‐Bromobenzophenone was converted to (4‐bromophenyl)‐phenyldichloromethane using phosphorus pentachloride. The dichloro compound was reacted with methoxide ion to form 4‐bromobenzophenone dimethylketal which was subsequently converted to its Grignard reagent, carboxylated with 14CO2, and acid hydrolyzed to the final product. Using excess Grignard reagent, virtually quantitative conversion of 14CO2 to product was obtained.
Routine production of 2‐deoxy‐D‐[1‐11C]glucose : An alternative
Authors: van Haver D. , Rabi N. A. , Vandewalle M. , Goethals P. , Vandecasteele C.
Published: October 2006

The routine production of 2‐deoxy‐D‐[1‐11C]glucose (11C‐glucose (11C‐2DG) from [11C]hydrogen cyanide and 2,3:4,5‐di‐O‐isopropylidene‐1‐iodo‐D‐arabinitol is described. The nitrile intermediate is purified by high‐performance liquid chromatography (HPLC) before reduction/hydrolysis with Raney alloy in formic acid. The radiopharmaceutical is isolated by ion exchange and is obtained in a radiochemical yield of 20 % with a synthesis time of 50–55 min. A typical run affords 25–30 mCi of 11C‐2DG with a specific activity of 90–100 mCi/mg.
Synthesis of (2R)‐ and (2S)‐[3‐2H]‐valine
Authors: Easton Christopher J. , Findlay Nicola G.
Published: October 2006

(2R)‐Valine and the (2S)‐isomer were esterified and bezoylated. The derivatives were chlorinated at C‐3 by treatment with sulphuryl chloride, reduced to the 3‐2H derivatives by reaction with triphenyltin deuteride, then hydrolysed to give (2R)‐ and (2S)‐[3‐2H]‐valine. The labelling is achieved with complete retention of optical purity.
Aromatic fluorination with N.C.A. F‐18 fluoride: A comparative study
Authors: Berridge M. S. , Crouzel C. , Comar D.
Published: October 2006

Fluorination of aromatic rings with no carrier added (n.c.a.) 18F‐fluoride was investigated using aryl triazenes and aryl iodides as substrates. Aryl triazenes give low yields of labeled under all conditions, and evidence was obtained to indicate that an inert solvent was unnecessary for the reaction. Nucleophilic substitution of aromatic iodides in DMSO was found to be a superior method of fluorination yielding up to 70% incorporation of label. The scope and limitations of this new labeling reaction are reported.
Synthesis of tritium‐labelled iohexol
Authors: Herscheid J. D. A. , Jacobsen T. , Skinnemoen K. , Valk J. , Hoekstra A.
Published: October 2006

In an efficient three‐step synthesis [3H] glycerol was converted into α‐tosyl‐ [3H] glycerol (yield: 77%), from which [3H] iohexol was prepared in an overall radiochemical yield of 25% and a specific activity of 400 m̈Ci/mmol. Performing the synthesis on a microscale, the overall yield decreased to only 4%, but a 99% pure [3H] iohexol with a specific activity of 1 Ci/mmol was obtained.
Synthese de la Letosteine: Marquee AU 14C ET AU 35S
Authors: Nicolas Colette , Gachon Francloise , Faurie Michel
Published: October 2006

LETOSTEINE, 2‐[1ethoxy carbonyl methylthio)‐ethyl] 4‐hydroxycarbonyl thiazolidine is labelled with either carbon‐14 or Sulfur‐35 on the following positions:

‐ the carboxylic carbon of the ester function by means of chloro (1‐14C)‐acetic acid.

‐ the thiazolidinyl group by means of L‐(35S)‐cysteine.

Specific activities are 0,373 mCi/mMole or 13,8 MBq/mMole for 14C‐LETOSTEINE and 9,90 mCi/mMole or 366 MBq/mMole for 35S‐LETOSTEINE.
Synthesis of carbon‐14 and deuterium labeled 3‐isobutyryl‐2‐isopro‐pylpyrazolo [1, 5‐a]pyridine
Authors: Nagatsu Yoshio , Takagi Koichi
Published: October 2006

In order to study the metabolic fate of 3‐isobutyryl‐2‐isopropylpyrazolo [1, 5‐a]pyridine (I, KC‐404: antiasthmatic agent) in experimental animals and humans, the synthesis of I labeled with carbon‐14 or deuterium was investigated. Carbon‐14 labeled I was obtained from 5 mCi of isobutyric acid‐1‐14C sodium salt with a 67.7% yield. Its specific activity was 24.7 m̈Ci/mg. Deuterium labeled I was synthesized from pyridine‐d5 with a 17.8% yield, which resulted in about 50% replacement of deuterium with hydrogen at the position 7 in I. The release of deuterium apparently did not occur on GC‐MS. The mixture of deuterium labeled I and unlabeled I (2:1 mole ratio) supplied nearly the same intensity of triplet ions (ion clusters) used for identification of I and its metabolites.
Synthesis of 14C‐labelled 2‐[2‐cyclohexylcarbonyloxy‐3‐{4‐(2‐pyridyl) piperazin‐1‐yl}propyl]‐3aα, 4β, 7β, 7aα‐tetrahydro‐4, 7‐methano‐isoindole‐1,3(2H)‐dione dihydrochloride (E‐0713)
Authors: Miyake Kazutoshi , Chiku Shigeru , Sohda Shigeru
Published: October 2006

A 14C‐labelled form of the antidiabetic compound E‐0713 was synthesized for pharmacokinetic and metabolic studies in six steps, using maleic anhydride [2,3‐14C] as the labelled starting meterial.
Synthesis of C‐13 labeled vitamin E, [4′a‐13C]all‐rac‐α‐tocopherol1)
Authors: Urano Shiro , Muto Riko , Matsuo Mitsuyoshi
Published: October 2006

Vitamin E with a 13C‐labeled isoprenoid side chain, [4′a‐13C]‐all‐rac‐α‐tocopherol (1), was synthesized by the coupling reaction of 6‐methoxymethoxy‐2‐([4‐methyl‐13C]5‐bromo‐4‐methyl‐pent‐l‐yl)chroman (8) with 3,7‐dimethyl‐1‐(thiazolin‐2‐yl) thio‐2,6‐octadiene (9). Compound 8 was prepared using 2‐(4,4‐diethoxycarbonylbut‐1‐yl)‐6‐methoxymethoxy‐2,5,7,8‐tetramethyl‐chroman (5) as a key intermediate and [13C]methyl iodide as a 13C source. The total yield of the labeled α‐tocopherol based on [13C]methyl iodide was 58.7%.
Synthesis of 2‐n butyl 3‐(3,5‐125diiodo 4‐(N, N‐diethylamino 2‐ethoxybenzoyl)) benzofuran hydrochloride (125I amiodarone)
Authors: Sion R.
Published: October 2006

125I Amiodarone was prepared by iodination of 2‐n butyl 4‐hydroxy 3‐benzoyl benzofuran with Na125I in alkaline medium. By amination with N, N‐diethyl 2‐amino 1‐chloroethane, 125I amiodarone was obtained with 30 % yield and a specific activity of about 1 Ci/mmol.
Synthesis of |24‐14C|‐3β,14β,20ε‐trihydroxy‐23‐nor‐5β‐cholanoic acid
Authors: Maier M. S. , Seldes A. M. , Gros E. G.
Published: October 2006

The synthesis of |24‐14C|‐3β,14β,20ε‐trihydroxy‐23‐nor‐5β‐cholanoic acid was accomplished by Reformatsky reaction of ethyl |1‐14C|‐bromo acetate with 3β‐acetoxy‐14β‐hydroxy‐5β‐pregnan‐20‐one which was obtained from digitoxigenin. The final and intermediate products were characterized by spectroscopic (IR, 1H and 13C‐NMR, MS) methods.
Synthesis of 1‐13C‐1‐indanone and 2‐13C‐1,2,3,4‐tetrahydroquinoline
Authors: Pickering R. E. , Wysocki M. A. , Eisenbraun E. J.
Published: October 2006

The synthesis of 2‐13C‐1,2,3,4‐tetrahydroquinoline (5) via 1‐13C‐3‐phenylpropanoic acid (1), 1‐13C‐1‐indanone (2), 1‐13C‐1‐indanone hydrazone (3) and 2‐13C‐3,4‐dihydro‐2(1H)‐quinolinone (4) proceeded in 78, 96, 95, 79, and 85% individual yields respectively for 1, 2, 3, 4, 5 and 61% overall yield of the latter from 1.
Synthesis of 14‐methyl[2,3‐3H]hexadecanoic acid
Authors: Helmich O. , Streibl M. , Filip J. , Hradec J.
Published: October 2006

14‐Methyl[2,3‐3H]hexadecanoic acid of a specific radioactivity of 51 Ci/mmol was prepared starting from 12‐methyl‐tetradecanoic acid isolated from wool fat. This fatty acid was converted into 12‐methyltetradecanal which was reacted with ethyl diethylphosphonoacetate to yield 14‐methylhexadecen‐2‐oic acid. The resulting compound was tritiated with gaseous 3H2 in the presence of a 5% Pd/BaSO4 catalyst. The reaction in dried dioxane gave products of a specific radioactivity corresponding to 87.9% of the theoretical value.
Synthesis of 1‐(2‐deoxy‐2‐fluoro‐β‐D‐arabinofuranosyl)‐5‐iodo [2‐14C] uracil
Authors: Swigor J. E. , Pittman K. A.
Published: October 2006

The synthesis of the title compound (7) is described. [2‐14C] cytosine (1) is treated with an aqueous mixture of sodium bisulfite and sodium sulfate at 80°C for 30 min. The resulting solid is then treated with aqueous sodium hydroxide and passed through a cation exchange column, producing [2‐14C] uracil (2). Iodionation with iodic acid and iodine in acetic acid yielded 5‐iodo‐[2‐14C]uracil (3) Treatment of (3) with hexamethyldisilazane formed the trimethylsilated pyrimidine. Condensation with 3‐0‐acetyl‐5‐0‐benzoyl‐2‐deoxy‐2‐fluoro‐D‐arabinosyl bromide produced a mixture of α, β isomes. Separation by column chromatography and saponification with aqueous potassium carbonate yielded the title compound.
Assessment of 99mTc‐labelled gentamicin in renal functional imaging
Authors: Özker Kutlan , Urgancioǧlu Irfan
Published: October 2006

An aminoglycoside antibiotic, gentamicin is labelled with 99m Tc by the stannous chloride reduction. Scintigraphic studies and organ distribution of this agent in experimental animals showed a selective renal localization. The radioactivity remained for a relatively long period in the kidneys suggesting some tubular reabsorption following filtration at the glomerular level. The concentration of 99m Tc‐gentamicin in the kidneys as a function of time has been studied by a gamma camera interfaced to a computer. Renal radioactivity clearance curves were generated from the regions of interests on each kidney. The potential value of 99m Tc‐gentamicin in the diagnosis of functional disorders with relation to the glomerular filtration and reabsorption in the proximal nephron is discussed.
Synthesis of carbon‐14 labeled cilobamine mesylate
Authors: Wagner E. R. , Hamilton C. T.
Published: October 2006

Cilobamine mesylate, cis‐2‐(3,4‐dichlorophenyl‐UL14C)‐3‐[(1‐methylethyl)‐amino]bicyclo[2.2.2]octan‐2‐01 methanesulfonate 1, a new antidepressant, was synthesized in 15% yield from the Grignard reaction of 1‐bromo‐3,4‐dichloro‐benzene‐UL14C and 3‐[(1‐methylethyl)amino]bicyclo[2.2.2]octan‐2‐one, 5. The bicycloketoamine 5 was prepared in three steps from bicyclo[2.2.2]oct‐2‐ene.
Synthesis of no‐carrier‐added radiobrominated N‐alkylated analogues of spiperone
Authors: Moerlein S. M. , Laufer P. , Stöcklin G.
Published: October 2006

The synthesis of a series of p‐bromo‐3‐N‐alkyl spiperone analogues is described. N‐alkylation was achieved via reaction of the potassium salt of the spiperone lactam ring with alkyl iodide; subsequent reactions with elemental bromine gave the p‐brominated isomers. Optimization studies using no‐carrier‐added (n.c.a.) 77Br− indicated that radiobromination of N‐alkyl spiperone analogues occurs with higher yields and in shorter reaction times when dichloramine‐T (DCT) is used rather than H2O2/acetic acid as an oxidant. The production of the title compounds in high effective specific activity with radiochemical yields of 20–30 % using n.c.a. 77Br− and DCT is reported.