bluuebunny/crossref_metadata_2025_split huggingface dataset:
The synthesis of the 2H, 3H, and 14C‐isotopomers of 2′‐deoxy‐2′,2′‐difluorocytidine hydrochloride, an anti‐tumor compound
Authors: Wheeler William J. , Mabry Thomas E. , Jones C. David 
Published: October 2006

AbstractThe 2H, 3H, and 14C‐isotopomers of 2′‐deoxy‐2′,2′‐difluorocytidine hydrochloride (1a, gemcitabine hydrochloride) have been synthesized in two radiochemical steps from the reaction of bis‐trimethylsilylcytosine‐[2‐14C] and 3,5‐O‐bis‐benzoyl‐1‐O‐methanesulfonyl‐2‐ deoxy‐2,2‐difluororibose (2b). A mixture of anomers of 3′,5′‐dibenzoyl‐2′‐deoxy‐2′,2′‐difluorocytidine (4a) or its 14C‐isotopomer (4b) were obtained which were readily separated by crystallization from ethyl acetate. Deprotection using methanolic ammonia yielded the target compound. The 2H and 3H‐isotopomers were prepared by deuterium (or tritium) gas hydrogenolysis of 5‐iodo‐2′‐deoxy‐2′,2′‐difluorocytidine (5).
Synthesis and NMR‐analysis of deuterated and tritiated cyclooctyl acetic acid
Authors: Kaspersen Frans M. , Schlachter Irene H. G. , Funke Carel W. , Wagenaars Gerard N. , Mellema Jan‐Remt 
Published: October 2006

AbstractTo increase the bio‐availability of naturally occurring steroids, esterification of the 17‐hydroxy position is a useful approach. Besides (branched) alkanecarboxylic acids1) and cyclohexanecarboxylic acid2) also cyclooctyl acetic acid (1) was applied. To establish the biological fate of the cyclooctyl acetic acid part of steroids the tritiated molecule was synthesized (Figure 1). Cyclooctanone (3) was condensed with cyanoacetic acid3) and the resulting cyanide (4) was hydrolyzed to cyclooctenyl acetic acid (2a)4) which contained according to 1H NMR and 13C NMR 20% of the isomeric 2b(1H NMR (C2HCl3): 5,58 ppm (t, CH of 2a) and 5,63 ppm (br.s CH of 2b) 13C NMR(C2HCl3): 129,6 ppm (CH of 2a) and 115,0 ppm (CH of 2b)).
Syntheses of poly‐deuterated 9(O)‐methano‐Δ6(9α)‐prostaglandin I1 methyl esters
Authors: Tanaka Toshio , Bannai Kiyoshi , Hazato Atsuo , Manabe Kenji , Kurozumi Seizi 
Published: October 2006

AbstractTwo types of poly‐deuterated isocarbacyclin [9(O)‐methano‐Δ6(9α)‐prostaglandin I1] methyl ester have been synthesized for the use of GC‐MS quantitative analysis as internal standards and for the use of metabolic study as substrates. The 5,13,14‐2H3 derivative 2 was prepared via H‐D exchange, deuteroboration, and sodium borodeuteride reduction. The 2,2,3,3,4,4‐2H6 derivatives 3, 4 were prepared starting from tetrahydrofuran‐d8.
Preparation of valeric acids, pentenoic acids, and γ‐valerolactones labelled with deuterium
Authors: Tashiro Masashi , Tsuzuki Hirohisa , Mataka Shuntaro , Yonemitsu Tadashi 
Published: October 2006

Abstract[2‐2H1]‐, [2,3‐2H2]‐, [2,2,3‐2H3]‐, and [4,4,5,5,5‐2H5]Valeric acids, and trans‐ and cis‐2‐[2‐2H1]pentenoic acid and 4‐[4,5,5‐2H3]pentenoic acid have been synthesized from 2‐bromovaleric acid, trans‐2‐pentenoic acid, 2,3‐dibromovaleric acid, and 4‐pentynoic acid in 78% to 95% isotopic purity by employing Raney alloys or Aluminium powder in alkaline deuterium oxide. The reductions of trans‐3‐ and 4‐pentenoic acids, while smoothly proceeding with 10% Pd‐C as an additive in the reaction system, resulted in the formation of deuteriated valeric acid with over‐introduction of deuterium atoms. Use of 3,4‐dibromo‐valeric acid resulted in the dehydrobromination between C‐2 and C‐3 and the subsequent hydrolysis of the bromine at C‐4, to provide γ‐[2,3‐2H2]‐ lactone, which was also prepared from 4‐bromo‐trans‐2‐pentenoic acid in higher purity. Levulinic acid involves the incorporation of deuterium atoms at C‐3 and C‐5 upon the treatment with 10% NaOD‐D2O, followed by Cu‐Al alloy reduction, affording γ‐[3,3,4,5,5,5‐2H6]valerolactone.
Preparation of 4,4′‐diaminodiphenylmethane‐(2H4) for use as internal standard in the quantification of 4,4′‐diaminodiphenylmethane
Authors: Natangelo Marco , Bagnati Renzo , Fanelli Roberto , Gavinelli Marco , Ulbricht Claudia , Benfenati Emilio 
Published: October 2006

AbstractA simple method has been developed for the synthesis of 4,4′‐diaminodiphenylmethane‐(2H4) for analytical purposes in gas chromatography‐negative ion chemical ionization mass spectrometry (GC‐NICIMS). It consists in a proton‐deuterium exchange reaction of the diamine using deutero‐hydrochloric acid in deuterated methanol. The reaction was conducted at 60°C. Deuteration of the diamine in the ortho positions of the aromatic rings was observed after eight days in these conditions, using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy.
Catalytic reduction in the synthesis of tritiated (6R) and (6S) 5, 10‐dideaza‐5,6,7,8‐tetrahydrofolate
Authors: Cross Ann D. , Morimoto H. , Williams P. G. , Beardsley G. P. 
Published: October 2006

Abstract[3H] 5,10‐dideaza‐5,6,7,8‐tetrahydrofolate, DDATHF, was obtained by a two step process. First, 2n[3H2O] was produced in the reaction flask containing m[1HAc] by the reduction of n[PtO2] with 3H2, so that a 1[3H+]:18[3H+ + 1H+] ratio of solvent protic species in theory resulted. Secondly, subsequently added diethyl‐2‐acetyl‐5,10‐dideaza‐9,10‐didehydrofolate was reduced in this tritium labeled solvent with the pre‐reduced Adams catalyst and additional carrier free tritium gas which was introduced to a pressure of 722 torr. The resulting (6R) and (6S) [3H] diastereomers were individually isolated. Each had a specific activity of 11.2 Ci/mmol, and the locations of the incorporated tritium atoms were completely determined by 1H decoupled 320 MHz 3H NMR by comparison with the 300 and 500 MHz 1H NMR spectra of [1H] (6S) DDATHF, [1H] (6R) DDATHF, and [5‐2H (50% 2H), 6‐2H (100% 2H), 7‐2H (50% 2H), 9‐2H (50% 2H), 10‐2H (50% 2H)] (6RS) DDATHF.
Stereoselective synthesis of stable isotope‐labeled L‐α‐amino acids: Biosynthesis of 2H‐, 13C‐, and 15N‐labeled L‐serines
Authors: Hanners John , Gibson Rowena , Velarde Karen , Hammer Judy , Alvarez Mark , Griego Janet , Unkefer Clifford J. 
Published: October 2006

AbstractWe have developed a stereospecific biosynthesis of 13C‐ and 15N‐labeled L‐serine which involves the serine‐type methylotroph Methylobacterium extorquens AM1. In this biosynthesis, C‐3 of serine is derived from methanol while C‐2, C‐1 and the α‐amino group are derived from glycine. By starting with the appropriate labeling precursor, we can produce any of the 2H, 13C and/or 15N isotopomers of L‐serine. Using a 5‐L culture, 40–50 millimoles of L‐serine are produced; L‐serine and glycine are recovered from the growth medium and then separated chromatographically.
Synthesis of the muscle relaxant [14C]L‐637,510
Authors: O'Connor Stephen P. , Ellsworth Robert L. , Gatto Gregory , Sharp Merck , Dohme  
Published: October 2006

AbstractThe synthesis of (E)‐3‐(9‐chloro‐5,6‐dihydro‐1 1 H‐pyrrolo(2,1‐b)(3)‐benzazepin‐11‐ylidene)‐N, N‐dimethyl‐1‐[3‐14C]‐propanamine (Z)‐2‐butenedioate(1:1) (11, [14C]L‐637,510), a potential muscle relaxant product for which 14C‐labeling was required for metabolism studies, is described. Introduction of the label in the 3‐position of the propanamine side chain was accomplished in eight steps from sodium [14C]cyanide with an overall radiochemical yield of 4.8%.
Novel selective catalytic reduction with tritium: Synthesis of the GABAA receptor radioligand 1‐(4‐ethynylphenyl)‐4‐[2,3‐3H2]propyl‐2,6,7‐trioxabicyclo[2.2.2]octane
Authors: Palmer Christopher J. , Casida John E. 
Published: October 2006

AbstractProtection of the terminal alkyne function in 1‐(4‐ethynylphenyl)‐4‐(prop‐2‐enyl)‐2,6,7‐trioxabicyclo[2.2.2]octane with a trimethylsilyl group permits the selective catalytic reduction of the olefin moiety with tritium gas to give after deprotection 1‐(4‐ethynylphenyl)‐4‐[2,3‐3H2]propyl‐2,6,7‐trioxabicyclo‐[2.2.2]octane. The labeled product at high specific activity is an improved radioligand for the GABA‐gated chloride channel of insects and mammals and the intermediate 4‐[2,3‐3H2]propyl‐1‐[4‐[(trimethylsilyl)ethynyl]phenyl]‐2,6,7‐trioxabicyclo[2.2.2]octane is useful for studies on the metabolic activation of this selective proinsecticide.
Regio‐ and stereo‐controlled synthesis of [24,30‐14C]‐labeled‐2,3‐epoxysqualene
Authors: Xiao Xiao‐Yi , Prestwich Glenn D. 
Published: October 2006

Abstract[24,30‐14C]‐(3S)‐2,3‐Epoxysqualene and its racemate were synthesized by two convenient routes. The products have the label in a metabolically‐nonlabile position relative to the demethylation of lanosterol to cholesterol.
Synthese du Chlorure de 2‐(Dimethylaminophenyl)‐3,6‐Dimethyl Benzo [2‐14C]‐Thiazolium ou Thioflavine T
Authors: Verny M. , Nicolas C. , Veyre A. 
Published: October 2006

Abstract14C‐Thioflavine T hydrochloride, labelled at the 2‐position of the thiazole ring, is synthesized from 4‐dimethylamino [14CO2H]benzoic acid, obtained from Ba 14CO3. The radiochemical yield is 76 %.
Preparation of [13C2]DMS
Authors: Beerli René , Borschberg Hans‐Jürg 
Published: October 2006

AbstractAn expedient two‐step synthesis of [13C2]DMSO, starting from commercially available [13C]methyl iodide, is described. The product obtained in 57% yield is of high chemical (≥ 99%) and isotopic purity (= 98% 13C2, 2% 13C1), as jugded by NMR‐spectroscopy and a GC‐MS‐assay.
Synthesis of radioiodo‐[4‐(2‐iodo‐4‐fluoro‐benzoyl)piperidin‐1‐yl]‐2′‐acetonaphthone
Authors: Mertens J. , Thomas M. 
Published: October 2006

AbstractRadioiodo‐[4‐(2‐1‐4‐fluorobenzoyl)piperidin‐1‐yl]‐2′‐acetonaphthone was synthesised as a potential in vivo tracer of the glutamate release inhibiting system. The labeling was performed by Cu1+ assisted non isotopic nucleophilic exchange on [4‐(2‐bromo‐4‐fluorobenzoyl)piperidin‐1‐yl]‐2′‐acetonaphthone.The labeled compound is obtained after HPLC separation and mini‐column recovery. The brominated substrate is obtained by Kl catalyzed coupling of 2‐bromo‐acetonaphthone to the piperidinyl entity in ethanol at room temperature using triethylamine.
Synthesis of nona‐deutero olivetol and nona‐deutero cannabinoids
Authors: Seltzman Herbert H. , Begum Mosammat K. , Wyrick Christopher D. 
Published: October 2006

AbstractCopper (I) catalyzed Grignard cross coupling of alkyl bromides provided a facile synthesis of d9‐olivetol [5‐(2,2,3,3,4,4,5,5,5‐2H9)pentyl‐1,3‐benzenediol] with high d9 incorporation levels and no detectable levels of d0 to d7 ions. The outcome of the coupling is dependent on which bromide is used as the Grignard reagent. d9‐Δ9‐THC and racemic d9‐11‐hydroxy‐Δ9‐THC suitable for GC/MS analysis were prepared from the olivetol.
Synthesis of [15N]‐procaine hydrochloride
Authors: Chiriac Maria , Pop Smaranda , Dordea Elisabeta 
Published: October 2006

AbstractThe synthesis of [15N]‐ labelled procaine hydrochloride, using (15NH4)2SO4 as starting isotopically labelled material, is presented. The experimental procedure is an adaptation of the synthesis methods for the corresponding unlabelled compounds.
Synthesis of tritiated threonine with a high specific activity
Authors: Delacotte Jean‐Michel , Galons Hervé , Schott Dominique , Morgat Jean‐Louis 
Published: October 2006

AbstractThe synthesis of the trichloromethyl analogue of benzyloxycarbonyl‐threonine is described. This precursor was reduced by tritium gas to give [methyl‐3H3]‐threonine and its allo isomer. They were separated by HPLC using a chiral stationnary phase. They have a molar specific activity of 3190 GBq/mmol, 86 Ci/mmol.
Synthesis of isotopically labelled 1,1′‐thiobis (2‐chloroethane) and some related compounds
Authors: Harrison J. M. 
Published: October 2006

Abstract1,1′‐Thiobis (2‐hydroxyethane) has been synthesized isotopically labelled with sulphur‐35, carbon‐13 and deuterium. The conversion to 1,1′‐thiobis (2‐chloroethane) labelled with sulphur‐35 and carbon‐13 is described.
Synthesis of ethyl [14CH3]methylmalonyl thioglycolate as a possible substrate analogue of [14CH3]methylmalonyl coenzyme‐A
Authors: Kovács I. , Kovács Z. 
Published: October 2006

AbstractEthyl methylmalonyl thioglycolate is a potential substrate analogue of methylmalonyl‐coenzyme‐A (methylmalonyl‐CoA) in the investigation of propionic acid metabolism. To prove this hypothesis, the tracer ethyl [14CH3]methylmalonyl thioglycolate was synthesized via methyl‐Meidrum's acid to carry out the biochemical examinations. The method described can also be used to synthesize [14CH3]methylmalonyl‐CoA by transesterification of active labelled methylmalonyl thiophenyl ester. This latter intermediate is chemically stable when stored at room temperature, and the unstable [14CH3]methylmalonyl‐CoA can be prepared in one step just preceeding the biochemical experiments.
Synthesis of (S)‐1‐[3‐hydroxy‐2‐(phosphonylmethoxy) propyl]‐[2‐14C]cytosine ((S)‐[14C] HPMPC)
Authors: Haynes U. J. , Swigor J. E. , Bronson J. J. 
Published: October 2006

AbstractThe synthesis of (S)‐[14C]HPMPC (4) is described. Heating [2‐14C]cytosine (1) in N, N‐dimethylformamide with (R)‐3‐0‐benzyl‐2‐0‐[(diethylphosphonyl)methyl]‐1‐0‐(methylsulfonyl) glycerol in the presence of cesium carbonate gave (S)‐1‐[3‐benzyloxy‐2‐(diethylphosphonylmethoxy) propyl]‐[2‐14C]cytosine (2). Reduction with palladium hydroxide on carbon in cyclohexene yielded (S)‐1‐[3‐hydroxy‐2‐(diethylphosphonylmethoxy)propyl]‐[2‐14C] cytosine (3). Deprotection of the diethylphosphonate ester with bromotrimethylsilane and treatment with water produced 190 mg of [14C] HPMPC (4) having a specific activity of 21.2 μCi/mg and a radiochemical purity 98.5% in an overall yield of 5.6%.
Stereoselective synthesis of stable isotope‐labeled L‐α‐amino acids: Chemomicrobiological synthesis of 13C‐ and 2H‐labeled L‐cysteine
Authors: Unkefer Clifford J. , Hanners John L. , Ehler Deborah S. 
Published: October 2006

AbstractTryptophan synthase catalyzes the nucleophilic replacement of the hydroxyl group at C‐3 of L‐serine. This enzyme can use benzyl mercaptan as a nucleophile in the conversion of serine to S‐benzyl‐L‐cysteine which is deblocked by treatment with sodium in liquid ammonia to yield L‐cysteine. A strain of E. coli engineered to overproduce tryptophan synthase was used in the conversion of L‐serine to L‐cysteine. Labeled serine was prepared biosynthetically as described previously.
[2‐14C] 5‐fluorouracil metabolism to [14CO2]
Authors: Rabinowitz Joseph L. 
Published: October 2006

AbstractThe rate of 14CO2 production from 2‐14C‐5‐FU was measured in rats bearing the Novikoff ascites hepatoma. Tracer amounts were injected and 14CO2 collected over a 6‐hour period. As the tumor cells proliferated the rate of 2‐14C‐5‐FU oxidation decreased markedly over the approximately 12± 2 days between implantation of tumor cells and death. On the day of innoculation of tumor cells, oxidation proceeded nearly linearly until almost 50% of the injected 2‐14C‐5‐FU was converted to 14CO2 in about 4 hours. With time after tumor innoculation, the rate of 14CO2 collection declined; ten days after innoculation only about 27% was oxidized by 4 hours, and at the terminal stage it declined to about 18% over 4 hours. Calculated from the time curves, the time oxidation of 25% of the injected trace dose increased from 88± 27 min to 195± 42 min after ten days, to 300 ± 59 min at the moribund state after 12 ± 2 days.Similar decreases in oxidation rate of 5‐FU were observed during growth of a solid implanted mammary carcinoma and for two other 2‐14C‐labelled pyrimidines, uracil and thymine injected in trace quantities.By comparing cancer subjects with themselves at different time‐intervals from the onset of the disease and treatment, it might be possible to guage treatment dosages in the progress of the disease.
Synthesis of (6R,7R)‐7‐[2‐(5‐aminio‐1,2,4‐[5‐14C]thiadiazol‐3‐yl)‐(Z)‐2‐methoxyimiyiminoacetamido]‐3‐[(4‐carbamoyl‐1‐quinuclidinio)methyl]ceph‐3‐em‐4‐carboxylate([14C]E1040)
Authors: Sugiyama Isao , Nomoto Seiichirou , Mizuo Hitoshi , Yamauchi Hiroshi 
Published: October 2006

Abstract(6R,7R)‐7‐[2‐(5‐amino‐1,2,4‐thiadiazol‐3‐yl)‐(Z)‐2‐methoxyiminoacetamido]‐3‐[4‐(carbamoyl‐1‐quinuclidinio)methyl]ceph‐3‐em‐4‐carboxylate (E1040), a new injectable cephalosporin with potent antipseudomonal activity, was synthesized labelled with carbon‐14, starting from potassium [14C]thiocyanate with 2‐(N‐chloroamidino)‐2‐(methoxyimino)acetic acid (I) gave (5‐amino‐1,2,4‐[5‐14C]thiadiazol‐3‐yl‐2‐methoxyimino)acetic acid (II). 7‐Amino‐3‐[(4‐carbamoyl‐1‐quinuclidinio)methyl]ceph‐3‐em‐4‐carboxylate hydrochloride (IV) was acylated with the above acid chloride using the PCl5 method, to afford the title compound (V); [14C]E1040, having a specific activity of 3.74 MBq/mg (as its anhydride), was obtaind in 47% overall radiochemical yield, with a radiochemical purity of more than 98.1%.
Synthesis of 4‐ and 10‐deuterated neryl and geranyl‐β‐D‐glucosides and their use in corroboration of a mechanism proposed for the fragmentation of heterosides in tandem mass spectrometry
Authors: Salles Christian , Jallageas Jean‐Claude , Beziat Yves , Cristau Henri‐Jean 
Published: October 2006

AbstractIn order to corroborate a mechanisms proposed for the fragmentation of the molecular ion of heterosides, involving a hydride migration from the aglycome to the osidic unit, the 4‐[2H2]‐10‐[2H3]‐labelled neryl and geranyl‐β‐D‐glucosides 9 and 10 have been synthesised.Deuterated ketone 1 was prepared in >99% isotopic abundance by base catalysed exchange with [2H2]‐water, and was reacted under Wittig‐Horner conditions furnishing the corresponding α, β‐unsaturated esters 3 and 4.Selective reduction of the ester group can be performed with DIBAl‐H, whereas LiAlH4 give a secondary reduction of the CC double bond.The published procedure (13) for the β‐D‐glucosidation of alochols has been modified in order to optimise conditions on the deuterated nerol and geraniol.By comparison of collision spectra (NICI/CAD) of pure deuterated and undeuterated neryl and geranyl‐β‐D‐glucosides the proposed fragmentation mechanism is fully corroborated.
Preparation and evaluation of cationic 99Tc/99mTc dimethoxy‐ and diethoxy‐hexanedione dioxime complexes
Authors: Su Z. F. , Linse K. H. , Steinmetz H. J. , Schwochau K. 
Published: October 2006

AbstractThe new ligands 1,6‐dimethoxy‐3,4‐hexanedione dioxime (DMHD) and 1,6‐diethoxy‐3,4‐hexanedione dioxime (DEHD) were synthesized and their boron containing 99Tc/99mTc complexes, formed by reduction of pertechnetate with BH4‐, were isolated, purified and characterized by IR/UV/VIS spectroscopy and FAB mass spectrometry. These rather stable cationic complexes differ significantly in lipophilicity as assessed by their octanol/saline partition coefficients and HPLC capacity factors. Unexpectedly the organ uptake and clearance of both complexes in mice proved to be very similar with only the uptake of 99mTc‐DMHD in the kidneys being enhanced.
Synthesis of deuterated polyethylene glycols
Authors: Schnabel Ruth 
Published: October 2006

AbstractThe synthesis of polyethylene glycols [α‐Hydro‐ω‐hydroxypoly(oxy‐1, 2‐ethanediyl)‐dx], deuterated in the chain, up to the lenght of the chain of 20 carbons was achieved by reaction of ethylene glycol‐d, with iodine as catalysts.
The preparation of 14C‐labeled FK‐506
Authors: O'connor Stephen P. , Ellsworth Robert L. , Omstead Mary Nallin , Jenkins Rosalind G. , Kaplan Louis 
Published: October 2006

AbstractUtilizing sodium [1−14C]propionate as a precursor, [14C]FK‐506, labeled at carbon atoms 10, 16, 18, 21a, 24, and 26, was produced by fermentative biosynthesis. Extractive isolation followed by chromatographic purification provided material of purity suitable for metabolism studies.
An efficient synthesis of S‐γ‐[(4‐trifluoromethyl)‐phenoxy]benzenepropanamine‐[1‐14C] maleate, an important metabolite of fluoxetine hydrochloride
Authors: Wheeler William J. 
Published: October 2006

AbstractS‐γ‐[(4‐Trifluoromethyl)phenoxy]benzenepropanamine‐[1‐14C] maleate has been prepared in six steps from R‐(‐)1‐phenyl‐1,2‐ethanediol. The isotope was incorporated by the reaction of NaCN‐[14C] with the tert. butyldimethylsilyl ether of R‐(‐)1‐phenyl‐1,2‐ethane‐diol 2‐tosylate. Borane reduction and arylation, followed by salt formation yielded S‐γ‐[(4‐trifluoromethyl)phenoxy]benzenepropanamine‐[1‐14C] maleate.
Synthesis of tritiated derivatives of the diphenylether herbicides acifluorfen and acifluorfen methyl
Authors: Mornet René , Gouin Lucien , Matringe Michel , Scalla René , Swithenbank Colin 
Published: October 2006

AbstractAcifluorfen 1 and acifluorfen methyl 2, two herbicides of the diphenylether family, are inhibitors of protoporphyrinogen oxidases. Two tritiated derivatives of these compounds, namely 3‐[3H]‐5‐[2‐chloro‐4‐(trifluoromethyl)phenoxy]‐2‐nitrobenzoic acid [3H]‐1, and methyl 3‐[3H]‐5‐[2‐chloro‐4‐(trifluoromethyl)phenoxy]‐2‐nitrobenzoic acid [3H]‐2, have been synthesised from 3‐[3H]‐5‐hydroxybenzoic acid, in order to probe their interactions with the target enzymes.
Synthetic strategies in the preparation of regiospecifically chlorine‐37 labeled polychlorinated dibenzo‐p‐dioxins
Authors: Mahiou Belaid , Deinzer Max L. 
Published: October 2006

AbstractA series of thirteen regiospecifically chlorine‐37 labeled polychlorodibenzo‐p‐dioxins were synthesized via the Sandmeyer reaction. Nitrochlorodibenzodioxins which were obtained by a base promoted condensation of catechols and dinitropolyhalobenzenes were reduced and converted to the diazonium salts. Chlorine‐37 was introduced using cuprous chloride‐37. The isotopic enrichment was in the range 75‐96%.
A chiral synthesis of dapoxetine hydrochloride, a serotonin reuptake inhibitor, and its 14C isotopomer
Authors: Wheeler William J. , O'bannon Douglas D. 
Published: October 2006

AbstractThe 14C‐isotopomer of dapoxetine‐[14C] HCl (S (+)‐N,N‐dimethyl‐α‐[2‐(1‐naphthalenyloxy)ethyl‐2‐14C]benzenemethanamine hydrochloride, 1a), a potent serotonin re‐uptake inhibitor has been prepared by a chiral synthesis, starting with tert.‐butyloxyphenylglycine (3). Borane reduction, followed by activation of the resulting alcohol 4 as its mesylate 5b, provided the chiral starting material. The radiolabel was introduced by reaction of 5b with sodium cyanide‐[14C]. The desired product (1) was then elaborated from nitrile 6a,b via a five step synthesis in an overall 19.5% radiochemical yield.
A microscale synthesis of a promising radiolabelled antitumor drug: Cis‐1,1‐cyclobutanedicarboxylato (2R)‐2‐methyl‐1,4‐butanediamine platinum(II), NK121
Authors: Suwa Masato , Kogawa Osamu , Nowatari Hiroyoshi , Murase Yuko , Homma Yoshio , Hashimoto Yutaka 
Published: October 2006

AbstractA promising antitumor drug, cis‐1,1‐cyclobutane‐dicarboxylato (2R)‐2‐methyl‐1,4‐butanediamine platinum(II), NK121, was synthesized from radionuclides of platinum such as 193mPt, 195mPt and 191Pt which were produced by neutron irradiation of enriched 192Pt. The overall yield was 38.6% in a synthesis time of 10 hours. The radioactivities present in 8.39 mg of NK121 were 115.3 μCi as 193mPt, 29.9 μCi as 197Pt, 22.0 μCi as 195mPt, and 4.8 μCi as 191Pt at the end of synthesis. The specific activity of the NK121 was 13.7 μCi (193mPt)/mg NK121 at the end of synthesis. The radiochemical purity of NK121 was typically 99 %. HPLC analyses confirmed that NK121 was in an adequate chemical purity and suitable for animal experimentation.
Preparation of 14C‐ and 18O‐enriched allyl alcohol (propanol free)
Authors: Kupczyk‐Subotkowska Lidai , Shine Henry J. 
Published: October 2006

AbstractPreparations of specifically labeled [1‐14C]‐, [3‐14C]‐ and [1‐18O]allyl alcohol are described. The syntheses were achieved, respectively, in 7, 11 and 9 steps, with overall yields of 33%, 10% and 38%.Commercially available K14CN, CH314COONa and H218O were used as the starting materials.