bluuebunny/crossref_metadata_2025 huggingface dataset:
Synthese de Δ8 et Δ9 ‐ tetrahydrocannabinol deuteries et trities
Authors: Hoellinger Henri , Nam Nguyen‐Hoang , Decauchereux Jean‐François , Pichat Louis
Published: October 2006

Cross‐coupling of 3,5‐dimethoxybenzyl bromide and 4‐buten‐magnesium bromide in presence of Li2CuCl4 afforded 1‐(3,5‐dimethoxyphenyl)‐4pentene. Demethylation of the latter by methylmagnesium iodide in xylene gave rise to 4′,5′‐dehydro‐olivetol. The latter, condensed with trans‐p‐mentha‐2,8‐dien‐1‐ol in the presence of either boron trifluoride etherate or p‐toluenesulfonic acid, gave 4′,5′‐dehydro‐Δ9‐ and Δ8‐THC respectively. 4′,5′‐dehydro‐Δ8‐THC was also obtained by isomerization of 4′,5′‐dehydro‐Δ9‐THC. Catalytic selective reduction of these precursors with deuterium or tritium, in the presence of tris(triphenylphosphine)rhodium chloride, afforded Δ9‐THC‐4′,5′,‐2H or Δ9‐THC‐4′,5′‐3H (50 Ci/mMole) and Δ8‐THC‐4′,5′‐2H or Δ8‐THC‐4′,5′‐3H (56 Ci/mMole).
Indium labeled particles for lung imaging: Homogeneous and heterogeneous phase reactions
Authors: Moore David H. , Shani Jashovam , Wolf Walter
Published: October 2006

The labeling of microspheres with In, intended as potential lung and capillary‐bed imaging agents, was studied using an EDTA‐exochelator to specifically bind indium. Incubation of the azo‐phenyl‐EDTA‐microsphere with indium, resulted in an unstable preparation which primarily localized in the liver and spleen. When, however, 111In was reacted with the diazo‐phenyl‐EDTA in solution, and this complex then coupled to the microspheres, excellent binding resulted. Similarly, complexing of In to azo‐phenyl‐EDTA‐albumin in solution followed by aggregation, also yielded radiolabeled particles which were resistant to washing and localized over 90% in the lung, immediately upon injection to rats. These results have been rationalized by proposing a mechanism where the kinetics of homogeneous and heterogeneous phase reactions account for the nature of the different products formed. The present study, while it leads to better indium microspheres and aggregates than recorded in the literature, above all points out to the need of a better understanding of reaction kinetics in the preparaation of such radiopharmaceuticals.
Synthesis of deuterium‐labelled drugs, of abuse for use as internal standards in, quantification by selected ion monitoring. II. Deuterium‐labelled benzodiazepines: Chlordiazepoxide, demethyldiazepam, diazepam, and oxazepam
Authors: Fentiman Allison F. , Foltz Rodger L.
Published: October 2006

Four deuterium‐labelled benzodiazepines were prepared for use as internal standards in the quantification of chlordiazepoxide, demethyldiazepam, diazepam, and oxazepam at low levels in body fluids by selected ion monitoring. The method described provides a way to introduce cleanly and in high isotopic purity five deuterium atoms into each drug.
Acetylation with acetic‐1–13‐C pivalic anhydride
Authors: Horton Walter J. , Adams Steven P. , Niermeyer Mary W.
Published: October 2006

In situ formation of acetic‐1–13‐C pivalic anhydride constitutes a convenient and economical means of preparing C‐13 containing acetanilides in excellent yield. Similarly, in situ formation of pivalic anhydride yields pivanilides. An elegant synthesis of p‐acetylaminobenzaldehyde from p‐nitro‐benzaldehyde via the acetal is described.
Synthesis of tritium‐labelled 7α‐hydroxy and 7β‐hydroxy dehydroepiandrosterone
Authors: Couch R. A. F. , Skinner S. J. M.
Published: October 2006

Tritium labelled 7α‐hydroxy and 7β‐hydroxy dehydroepiandrosterone were synthesised by the allylic acyloxylation of [1,2‐3H(n)] dehydroepiandrosterone‐3β‐acetate with t‐butylperbenzoate. The 7α epimer was of comparable specific activity to the substrate.
A convenient method for synthesis of 14C‐carbonyl methylcarbamates
Authors: Hurst Harrell E. , Dorough H. Wyman
Published: October 2006

While [14C‐carbonyl]‐methyl isocyanate has been used widely for the preparation of radioactive insecticidal methylcarbamates, yields are often low, and in some cases reactions completely unsuccessful, because of the sensitivity of the isocyanate to moisture. This paper described a process whereby the [14C]‐methyl isocyanate, in its break‐seal container as received from the supplier, is reacted with the appropriate oxime or phenolic intermediate without exposing the isocyanate to atmospheric moisture. Results are presented for the insecticides carbaryl, carbofuran, aldicarb and methomyl demonstrating consistent yields of 85 to 95% using a procedure of uncommon simplicity.
Synthesis of 14‐14C‐adriamycin
Authors: Vishnuvajjala Babu R. , Kataoka Tadashi , Cazer Frederick D. , Witiak Donald T. , Malspeis Louis
Published: October 2006

14‐14C‐Adriamycin HCI has been prepared from unlabeled adriamycin. The 14C‐Diazald served as the source of the label. This synthesis does not require protection of the phenolic hydroxyl groups.
Labelling of neuroleptic butyrophenones. 1. syntheses of haloperidol‐14C and trifluperidol‐14C
Authors: Nakatsuka Iwao , Kawahara Kazuo , Kamada Takeshi , Yoshitake Akira
Published: October 2006

4‐[4‐(4‐Chlorophenyl)‐4‐hydroxypiperidino]‐4′‐fluorobutyrophenone (haloperidol) (I) and 4′‐fluoro‐4‐[4‐hydroxy‐4‐(3‐trifluoromethylphenyl) piperidino] butyrophenone (trifluperidol) (II), neuroleptic drugs, were labelled at the carbonyl position with carbon‐14 for the use of metabolic studies. The syntheses were achieved according to the reaction scheme shown in Fig. 1. Cyclopropionic‐1‐14C acid (IV) was prepared from cyclopropyl bromide (III) by Grignard reaction with carbon‐14C dioxide. Condensation of IV with fluorobenzene, followed by ring‐opening with hydrogen chloride, gave 4‐chloro‐4′‐fluorobutyrophenone‐1‐14C (VI). After ketalization of VI, the ketal (VII) was condensed with corresponding piperidine derivatives (VIIIa and VIIIb) and subsequently hydrolized with hydrochloric acid to give haloperidol‐1‐14C (I) and trifluperidol‐1‐14C (II), respectively. The overall radiochemical yields of I and II from barium carbonate‐14C were 31 and 27%, respectively.
Labeled 2‐deoxy‐D‐glucose analogs. 18F‐labeled 2‐deoxy‐2‐fluoro‐D‐glucose, 2‐deoxy‐2‐fluoro‐D‐mannose and 14C‐2‐deoxy‐2‐fluoro‐D‐glucose
Authors: Ido T. , Wan C‐N. , Casella V. , Fowler J. S. , Wolf A. P. , Reivich M. , Kuhl D. E.
Published: October 2006

A convenient method for the synthesis of 18F‐2‐deoxy‐2‐fluoro‐D‐glucose (4) and 18F‐2‐deoxy‐2‐fluoro‐D‐mannose (8) by the direct fluorination of 3,4,6‐tri‐0‐acetyl‐D‐glucal with 18F‐F2 is described. 14C‐2‐deoxy‐2‐fluoro‐D‐glucose has been synthesized from 14C‐3,4,6‐tri‐0‐acetyl‐D‐glucal (from D‐[14c(U)]‐glucose) by fluorination with F2 (Method 1) and CF3OF (Method 2). These labeled analogs of 2‐deoxy‐D‐glucose were required for the study of local cerebral glucose metabolism.
Preparation of [1‐14C] and 35S‐labelled alkyl sulphonates
Authors: Taylor Andrew J. , Olavesen Anthony H. , James Colin
Published: October 2006

Undecyl, dodecyl and hexadecyl sulphonates were prepared with 14C‐label in the 1‐position. The syntheses require the formation of a Grignard intermediate from the appropriate n‐1 alkyl bromide followed by carboxylation of the Grignard with 14CO2 and subsequent esterification with diazomethane. Reduction of the ester with lithium aluminium hydride and conversion to the corresponding alkyl bromide provides a suitable 1‐14C labelled derivative for conversion to the required thiol which is readily oxidised to the corresponding sulphonate with retention of the label in the 1‐position. The synthetic route provides an acceptable overall yield (18–24%) of specifically labelled alkyl sulphonates of high purity. By using [35S]thiourea in the sequence 35S‐labelled dodecyl sulphonate was readily obtained. The identity and purity of the products was confirmed by mass spectrometry, infra‐red spectroscopy, t.l.c. and reverse‐isotope dilution.
A novel surface for high specific activity tritium labelling using microwave discharge activation of tritium gas
Authors: Ehrenkaufer Richard Lee E. , Wolf Alfred P. , Hembree Wylie C.
Published: October 2006

A 10 to 300 fold increase in specific activity has been realized in the microwave discharge activation (MDA) of tritium gas labeling of a variety of compounds, up to the Ci/mmol range by the use of a cellulose Millipore filter (CMF) as the labeling surface. New reaction systems have also been developed to accommodate these and other large samples as well as multiple samples.
Synthesis of 14C‐labeled inosine 5′‐phosphate
Authors: Sakata Shinji , Ikegami Shiro
Published: October 2006

14C‐Labeled inosine 5′‐phosphate was synthesized by direct phosphorylation of inosine‐8‐14C with phosphoryl chloride followed by hydrolysis of the resulting phosphorodichloridate. Isolation and recrystallization of its disodium salt afforded pure material in 66.8% overall chemical yield.
Synthesis of 14C‐endosulfan from 2,3 14C‐maleic anhydride
Authors: Huhtanen K. L. , Dorough H. W.
Published: October 2006

The insecticide endosulfan (5a,9a‐ 14C 6,7,8,9,10,10‐hexachloro‐1,5,5a,6,9,9a hexahydro‐6,9‐methano‐2,4,3‐benzodioxathiepin‐3‐oxide) was prepared from 2,3 14C‐maleic anhydride. The Diels‐Alder reaction of maleic anhydride with hexachloro‐cyclopentadiene yielded 1,4,5,6,7,7‐hexachlorobi‐cyclo [2.2.1] hept‐5‐ene‐2,3‐dicarboxylic acid anhydride. This anhydride was reduced to the corresponding carboxylic acid γ lactone with sodium boro‐hydride which was further reduced to the diol (1,4,5,6,7,7‐hexachloro‐2,3‐bis‐(hydroxymethyl) bicyclo [2. 2. 1] hept‐5‐ene) with lithium aluminum hydride. The later compound was reacted with thionyl chloride in carbon tetrachloride to give endosulfan.
A modified synthesis of tritium labelled amides from labelled carboxylic acids and amines using EEDQ as a reagent
Authors: Soudijn W. , van Wijngaarden I. , Knaeps A. G.
Published: October 2006

The reaction conditions for the preparation of amides from labelled carboxylic acids and amines using EEDQ (2‐ethoxy‐1 (2H)‐quinolinecarboxylic acid, ethyl ester) as a reagent were modified for the synthesis of the tritium labelled benzamide Halopemide (N‐{2‐[4‐(5‐chloro‐2,3‐dihydro‐2‐oxo‐ lH‐benzimidazol‐1‐yl)‐1‐piperidinyl] ethyl} −4‐fluorobenzamide), as EEDQ, reacted in an unexpected way, resulting in a 1:1 mixture of the benzamide and the N‐carbethoxy derivative of the starting amine and of “unreacted” carboxylic acid.

The basicity of the starting amine influenced the yield of the benzamide. By optimalizing the reaction conditions, it was possible to convert the labelled benzoic acid quantitatively into the benzamide.
Synthesis of carbon‐14 labelled acetaminophen (4‐hydroxyphenylacetamide, carbonyl‐14C)
Authors: Stavchansky S. , Wu P.
Published: October 2006

A simple and convenient method for the condensation of paminophenol (I) with 14C‐acetic anhydride (II) yields up to 76% of 14C‐labelled 4‐hydroxyphenylacetamide (carbonyl‐14C) (III). Typical synthesis time is 60 minutes. Radioactive yield is 51%, and specific activity is 0.22 μCi/mg.
Synthesis of some 2,3‐14C‐quinoxaline derivatives
Authors: Saari Walfred S. , Lumma William C.
Published: October 2006

6‐Chloro‐lH‐quinoxalin‐2‐one‐2,3‐14C was prepared by the novel condensation of 4‐chloro‐1,2‐phenylenediamine with glyoxylic acid‐14C (U). The labelled quinoxalinone was transformed further into 2,6‐dichloroquinoxaline‐2,3‐14C and 6‐chloro‐2‐(1′‐piperazinyl)‐quinoxaline‐2,3‐14C.
Synthesis of an intrinsically radiolabeled enkephalin analog: [p‐tritio‐phenylalanyl]4‐norleucyl5‐enkephalin
Authors: Day Alan R. , Freer Richard J.
Published: October 2006

In a previous study methionine‐enkephalin (H‐Tyr‐Gly‐Gly‐Phe‐Met‐OH) and four analogs and homologs were synthesized and compared to morphine with respect to their ability to inhibit electrically evoked contractions of the isolated guinea pig ileum. The compounds were: Tyr‐Gly‐Gly‐Phe‐Leu (Leu5‐enkephalin), Tyr‐Gly‐Gly‐Phe (des‐Met5‐enkephalin), Tyr‐Gly‐Gly‐Phe‐Nle (Nle5‐enkephalin) and Tyr‐Gly‐Gly‐[p‐chloro‐Phe]‐Nle ([p‐chloro‐Phe]4‐Nle5‐enkephalin). The IC50 concentrations on the guinea pig ileum assay were 3.0 × 10−7 M, 4.0 × 10−5 M, 1.1 × 10−7 M and 1.6 × 10−7 M respectively. The IC50 for Met5‐enkephalin was 5.0 × 10−8 M and for morphine 2.0 × 10−7 M. These data indicate that the methionine residue is important for biological activity and that norleucine is a more acceptable substitution at this position than is leucine. Therefore, the [p‐chloro‐Phe]4‐[Nle]5‐enkephalin was synthesized, dehalogenated by catalytic hydrogenation in the presence of 3H2 to yield the intrinsically labeled [p‐tritio‐Phe]4‐Nle5‐enkephalin. The labeled peptide (9 Ci/mmole) was completely stable for at least 9 months at −20°C in 50% aqueous acetic acid.
A synthesis of 1‐(1‐14C‐ethoxycarbonyl)‐2‐ethoxy‐1,2‐dihydroquinoline [14C‐EEDQ]
Authors: Robinson W. T.
Published: October 2006

A three step in situ micro synthesis is described for 1‐(1‐14C‐ethoxycarbonyl)‐2‐ethoxy‐1, 2‐dihydroquinoline [14C‐EEDQ]. Ethylchloroformate made from 1‐14C‐ethanol and phosgene is allowed to react with quinoline and subsequently ethanol in the presence of Na2CO3 to form 14C‐EEDQ.
A simple electrolytic method of labeling human fibrinogen, immune gamma globulin and serum albumin with 99mTc‐pertechnetate at pH 7.4
Authors: Wong Dennis W.
Published: October 2006

An improved electrolytic labeling technique has been developed for tagging human plasma proteins at physiologic pH condition. The basic principle involves the addition of protein after electrolysis and pH adjustment, thus avoiding harsh treatment of the protein and preserving its biological properties. High binding efficiency has been obtained for human fibrinogen, immune gamma globulin and serum albumin with an average of 77%, 86% and 87% respectively as assayed by paper radiochromatography. The labeling mechanism is not known. Data from protein electrophoresis demonstrate the existance of chemically active 99mTc‐complex species with high protein binding capacity. The entire labeling process requires less than 1 hour. Since plasma proteins are labeled at pH 7.4, the problem of protein denaturation has been significantly reduced.
A high yield synthesis of 2‐14C‐methimazole
Authors: Lee Philip W. , Gudzinowicz Michael J. , Neal Robert A.
Published: October 2006

2‐14C‐Methimazole was prepared in a condensation reaction between methylaminoacetaldehyde dimethyl acetal and potassium 14C‐thiocyanate in acidic medium. The yield of final product was 86.3% of theoretical with a radio purity of greater than 99.5%.
Labelled compounds of potential biological interest VI. Preparation of some labelled local anaesthetic aminoethers
Authors: Gosztonyi Tamas , Domeij Karl Erik , Sandberg Rune
Published: October 2006

2′‐(2‐Diisopropylaminoethoxy)‐butyrophenone (ketocaine) and 1‐butoxy‐2‐(2‐diisopropylaminoethoxy)‐benzene show a good anaesthetic effect on topical application. The synthesis of both of these compounds specifically labelled with 14C is described. The preparation of ketocaine generally labelled with tritium and specifically labelled with deuterium is also reported.
Nouvelle Methode De Synthese d'Olefines Deuteriees En Position Selective
Authors: Quintard J. P. , Pereyre M.
Published: October 2006

Tous les styrères mono, di ou tri‐deutériés sur la partie vinylique sont obtenus sélectivement par une méthode organostanique rapide et pratique.

Le procédé fait intervenier l'addition d'un hydrure (ou deutériure) organostannique au phénylacéne (deutérié ou non) suivie de transmétallation par le butyllithium et de réaction des lithiens vinyliques obtenus avec l'acide acétique (deutérié ou non).

De telles synthèsis sont susceptibles d'étre généralisées à un certain nombre d'autres systèmes vinyliques.
Non‐specific tritiation of some carcinogenic aromatic amines
Authors: Breeman G. E. M. , Kaspersen F. M. , Westra J. G.
Published: October 2006

2‐Aminofluorene, 4‐amino‐3‐methylbiphenyl, 4‐amino‐biphenyl and 4‐amino‐4′‐fluorobiphenyl were tritiated by acid catalyzed exchange of the corresponding nitro compounds followed by catalytic reduction. The exchange reactions were carried out by heating the nitro compounds in [3H]‐trifluoroacetic acid with a catalytic amount of trifluoromethanesulphonic acid (TFMS). No loss of tritium could be detected during the conversion of the tritiated nitro compounds into the corresponding amines by catalytic hydrogenation. Incorporation into the ortho position is very low (< 4%). During the metabolic activation and binding of the tritiated N‐acetyl‐2‐aminofluorene to rat liver DNA in vivo, no tritium exchange occurred.
Synthesis of potassium [14C] dicloxacillin
Authors: Ferdinandi E. S.
Published: October 2006

A synthesis of potassium [14C] dicloxacillin, labelled in the 3‐position of the isoxazole ring, is described. The compound, having the specific activity 21 mCi/mmole, was obtained in 30% overall yield from ethyl [3‐14C] acetoacetate.
Synthesis of 5‐nitrofuran‐2 [14C] aldehyde diacetate and the antibacterial agent [14C]‐nifuroxazide
Authors: Elsom L. F. , Hawkins D. R.
Published: October 2006

Furan‐2‐[14C] carboxylic acid has been prepared in 74% yield by carbonation of 2‐furyl‐lithium. Furan‐2‐[14C] aldehyde was isolated as the diacetate after catalytic reduction of the corresponding acid chloride. Nitration gave 5‐nitrofuran‐2‐[14C] aldehyde diacetate and after hydrolysis to the aldehyde was condensed with 4‐hydroxybenzhydrazide to give 5‐nitrofuran‐2‐[14C]‐aldehyde 4′‐hydroxybenzoylhydrazone, [14C]‐nifuroxazide, in an overall radiochemical yield of 15% from barium [14C]‐carbonate.
Synthesis of 14C‐labeled flame retardants. 14C‐labeled‐tetrabromophthalic anhydride and tetrabromobisphenol‐A
Authors: Susán Alexander B. , Ebert David A. , Duncan William P.
Published: October 2006

The multistep syntheses of tetrabromophthalic‐1,2,3,4,5,6‐U‐14C anhydride 6, and 3,5,3′,5′‐tetrabromo‐4,4′‐isopropylidenedi‐(phenol‐U‐14C) 11, are described. The synthesis pathway to 6 includes a novel preparation of phthalic acid‐1,2,3,4,5,6‐U‐14C acid from benzene‐U‐14C. Both 6 and 11 were obtained in 9% overall radiochemical yield (based on benzene‐U‐14C).
A simple method for the synthesis of specific [2H] and [3H]labelled methyl‐hydroxylated derivatives of 7,12‐dimethylbenz[a]anthracene
Authors: Fu Peter P. , Yang Shen K.
Published: October 2006

Specific [2H] and [3H]labelled methyl‐hydroxylated derivatives of 7,12‐dimethylbenz[a]anthracene (DMBA), 7‐hydroxymethyl‐12‐methylbenz[a]anthracene, 7‐methyl‐12‐hydroxymethylbenz[a]anthracene, and 7,12‐dihydroxymethylbenz[a]anthracene, were synthesized with good yield and high specific activity. The method involved two simple steps; oxidation of the unlabelled methyl‐hydroxylated DMBA to the corresponding formyl derivatives followed by reduction with either sodium borodeuteride or sodium borotriteride to yield the [2H] or [3H]labelled methyl‐hydroxylated derivatives with the isotope specifically attached to benzylic carbons.
Derivate von [103Ru]‐methyl‐ruthenocen Konstitution und Organ‐verteilung von Potentiellen Radiopharmaka
Authors: Schneider Michael , Wenzel Martin
Published: October 2006

Synthesis and organ distribution of the oxidation products of methylruthenocene up to ruthenocene acid and of various derivatives of hydroxymethylruthenocene labelled with 103Ru are described. Hydroxymethylruthenocene and ruthenocenecarboxaldehyde show like ruthenocene acid a comparable organ distribution and a high affinity to the kidneys. Probable hydroxymethylruthenocene and the aldehyde are oxidizid in vivo and then excreted as acid or as conjugate via kidneys. The benzoic acid ester of hydroxymethylruthenocene enriches in the adrenals with high contrast to kidneys. Tumor affinity of all compounds tested was low.
3‐(1,2‐Diphenylethyl)‐1,4,5,6‐Tetrahydro‐1,2,4‐Triazine‐3_14C Monohydrochloride
Authors: McKendry Lennon H.
Published: October 2006

3‐(1,2‐Diphenylethyl)‐1,4,5,6‐tetrahydro‐1,2,4‐triazine‐3‐14c hydrochloride (6) with a specific activity of 25.53 mCi/mmole was prepared in a 66.1% yield from benzyl cyanide‐1‐14C via a three step process.
Synthesis of Shikimic‐6‐13C acid
Authors: Hollstein Ulrich , Mock David L. , Sibbitt Randy R. , Roisch Uta , Lingens Franz
Published: October 2006

Shikimic‐6‐13C acid, 43 ± 5% enriched, was synthesized from 91% enriched acetic‐2‐13C acid via 91% enriched phosphoenolpyruvic‐3‐13c acid. The latter intermediate was condensed with erythrose‐4‐phosphate by a cell free extract of E. coli 83‐24.
Synthesis of deuterium and tritium labeled 2‐acetamido‐ 5,6‐dimethylbenzimidazole
Authors: Hsi Richard S. P. , Skaletzky Louis L.
Published: October 2006

Synthesis of 2‐acetamido‐5,6‐dimethylbenzimidazole, labeled with deuterium and tritium at the 4‐ and 7‐Dositions of the benzimidazole ring system, is described. 4,5‐Dimethyl‐O‐phenyl‐enediamine is deuterated and tritiated in the 3‐ and 6‐positions by means of exchange with deuterated and tritiated water. These relatively labile labels are rendered stable after formation of the benzimidazole rinq system. The stability of the labels in 2‐acetamido‐5,6‐dimethyl[4,7‐3H]benzimidazole is ascertained.
The enzymatic preparation of L(+)‐3‐hydroxy(3‐14C)butyrate
Authors: Dombrowski George , Chao Kuen‐Lan , Swiatek Kenneth R.
Published: October 2006

L(+)‐3‐hydroxy(3‐14C)butyrate was prepared by treating the D, L‐racemic mixture with the stereospecific D‐(−)‐3‐hydroxybutyrate dehydrogenase enzyme. The unfavorable equilibrium position of the dehydrogenase was overcome by the addition of acetaldehyde and alcohol dehydrogenase. The D‐isomer was converted by this treatment to acetoacetate. The unreacted L(+)‐3‐hydroxy(3‐14C)butyrate was then isolated by preparative silica gel chromatography in an overall yield of 65%.
A convenient method for production of 11C‐labelled glucose
Authors: Ehrin E. , Westman E. , Nilsson S.‐O. , Nilsson J. L. G. , Widen L. , Greitz T. , Larsson C.‐M. , Tillberg J.‐E. , Malmborg P.
Published: October 2006

A convenient photosynthetic method for production of 11C‐ labelled glucose has been designed using the green alga Scenedesmus obtusiusculus Chod. The organism converts H11CO3 to glucose in 50‐70% yield. The total time needed for the synthesis and isolation of the glucose is 25‐30 minutes.
The synthesis of 13‐cis‐retinoic acid‐6,7‐14C
Authors: Muccino Richard R. , Wasiowich Carol A.
Published: October 2006

A route to crystalline 13‐cis‐retinoic acid‐6,7‐14C (1) has been developed. Addition of acetylene‐1,2‐14C to 6‐methyl‐5‐hepten‐2‐one (4) gave dehydrolinalool‐1,2‐14C (5) which was catalytically transformed into citral‐1,2‐14C (6) and then condensed with acetone to give pseudoionone‐4,5‐14C (7). Ring closure of 7 gave β‐ionone‐6,7‐14C (8) which upon addition of vinyl Grignard give vinyl‐β‐ionol‐6,7‐14C (9). Conversion of 9 to its triphenylphosphonium salt 10 and condensation of the Wittig reagent from 10 with 4‐hydroxy‐3‐methylbut‐2‐enolide (11) gave a mixture from which pure 13‐cis‐retinoic acid‐6,7‐14C (1) could be crystallized.
A facile micromolar reduction of [1,2,3,4,10‐14C]aldrin to 6,7‐dihydro[1,2,3,4 10‐14C]aldrin
Authors: Lewis Neil J. , Cazer Frederick D.
Published: October 2006

The preparation of 6,7‐dihydro[1,2,3,4,10‐14C]aldrin is reported by catalytic reduction of [1,2,3,4,10‐14C]aldrin. Modification of previously published conditions afforded the desired product in 97.1% yield as assayed by electron capture gas chromatography. The convenient one vessel reaction proceeds rapidly to give the high purity product in twenty minutes at atmospheric pressure.
The preparation of aromatic astatine compounds through aromatic mercury‐compounds
Authors: Visser Gerard W. M. , Diemer Eduard L. , Kaspersen Frans M.
Published: October 2006

Aromatic astatine compounds can be prepared under mild conditions in high yields by reaction of astatine with aromatic mercury compounds.

Compared to direct electrophilic astatination this procedure is an easy and clean method for the introduction of astatine in aromatic compounds.
Tritiation of the nitroxide spin labeled fatty acid 14‐proxylstearic acid
Authors: Keana John F. W. , Boyd Steven A.
Published: October 2006

The nitroxide spin labeled fatty acid 14‐proxylstearic acid (1) was tritium labeled (likely at the 2‐position) by a platinum black catalyzed exchange reaction in tritiated hot aqueous potassium hydroxide. The recovery of pure tritiated 1 was 565, with a specific activity of 260 mCi/mM.
Electron spin resonance spectroscopy studies of 99Tc in aqueous solutions. Part II
Authors: Heitzmann Martin W. , Yang George C. , Ford Leonard A. , Benson Walter R.
Published: October 2006

The addition of NaNO2 to aqueous NH4TcO4 yielded paramagnetic Tc complexes when reduced in HCl solutions. Similar or identical complexes are produced by reduction of NH4TcO4 with hydroxyl amine in acidic, neutral, and basic solutions.
New synthesis of carbamate, thiocarbamate and urea type herbicides: Preparation of 14C‐labelled diuron and E P T C
Authors: Volford J. , Knausz D. , Meszticzky A. , Horváth L. , Csákvári B.
Published: October 2006

N,N‐dialkyl‐carbamic acid‐trimethylsilyl‐esters were synthesized starting with 14CO2. The new synthesis route is simple and provides good radiochemical yield. Silyl‐carbaminates directly or thorough carbamoyl‐halogenides may be used for preparation of labelled herbicides: carbamates, thiocarbamates and ureas.
Preparation of tritiated 2,4‐diamino‐5‐adamantyl‐6‐methylpyrimidine
Authors: Zakrzewski Sigmund F. , Evans E. Anthony
Published: October 2006

Tritium labeled 2,4‐diamino‐5‐adamantyl‐6‐methylpyrimidine was prepared by a platinum metal catalyzed tritium exchange for 4 hr at 70°. The crude material was purified on a Sephadex G‐25 column and converted to its water soluble ethanesulfonate salt. The analysis of the purified material revealed that 43% of the tritium was located in the 6‐methyl group and the remainder in the adamantane moiety of the molecule.
Synthesis of N‐(2‐piperidylmethyl)‐2,5‐BIS(2,2,2‐trifluoroethoxy)benzamide‐carbonyl‐14C acetate (flecainide‐14C acetate)
Authors: Banitt E. H. , Conard G. J.
Published: October 2006

N‐(2‐Piperidylmethyl)‐2,5‐bis(2,2,2‐trifluoroethoxy)benzamide acetate (flecainide acetate; R‐818), a new antiarrhythmic agent, was labelled with carbon‐14 at the carboxamide position for metabolic studies. A three‐step synthetic route starting from 2,5‐dihydroxybenzoic acid‐carboxyl‐14C provided chemically pure flecainide‐14C acetate in 37.0% overall yield. Thin layer chromatographic analysis indicated that the carbon‐14 labelled product (12.28 mCi/mmol) was at least 99.5% radiochemically pure.
Selenium incorporation into sulphur amino acids and glutathione and the stability of the incorporation products
Authors: Czauderna M. , Samochocka K.
Published: October 2006

The reaction of 75Se‐sodium selenite with cysteine, cystine and glutathione was studied. Selenodicysteine and selenodiglutathione were obtained as the incorporation products of inorganic selenium. The incorporation of selenium into these organic compounds is greatly affected by pH. The equilibrium constants of the selenodicysteine and selenodiglutathione formation were calculated. The stability of selenodicysteine in a strong acidic solution, in the hydrogen peroxide solution and in the presence of mercaptoethylamine were investigated. The mechanism of the decomposition of the investigated selenium compounds was suggested.
Preparation of tritium‐labeled 4‐hydroxy‐α‐[p‐(2‐(N‐pyrrolidinyl) ethoxy) phenyl]‐α′‐nitrostilbene (CN‐928), a biologically‐important metabolite of the antiestrogen CI‐628
Authors: Katzenellenbogen John A. , Tatee Tochiro , Robertson David W.
Published: October 2006

3‐3H‐4‐hydroxy‐α‐[p‐(2‐(N‐pyrrolidinyl)ethoxy)phenyl]‐α'‐nitro‐stilbene (3H‐CN‐928), a tritium‐labeled metabolite of the Park‐Davis antiestrogen CI‐628, was prepared by catalytic hydrogenolysis of the corresponding 3‐iodo‐CN‐928 with carrier‐free tritium gas. The precursor was prepared either by iodination of CN‐928, or by total synthesis from 3‐iodo‐4‐hydroxybenzoic acid. The final material was obtained with a specific activity of 22 Ci per mmole, which is sufficiently high for receptor binding studies.
A rapid synthesis of nitrogen‐13 labelled amphetamine
Authors: Finn R. D. , Christman D. R. , Wolf A. P.
Published: October 2006

The preparation of nitrogen‐13 labelled α‐methylphenyl‐ethylamine (amphetamine), utilizing a sealed reaction system is described.
Tritium incorporation into solvents under the conditions of catalytic dehalogenation
Authors: Černý B. , Hanuš J.
Published: October 2006

Incorporation of tritium into selected polar solvents was studied in the presence of bases and buffering substances. Tritium gas was used as a tritium source and the, reaction was catalyzed by PdO, Pd/BaSO4, Raney nickel.
Synthesis of 14C‐labeled O‐acetyl‐L‐serine, O‐benzoyl‐L‐serine, β‐N‐phenyl‐L‐asparagine, benzyl glycinate, and α‐dimethylaminoisobutyric acid
Authors: Adam William E. , Snook Edward W. , Curphey Thomas J.
Published: October 2006

Syntheses and analyses are described for β‐N‐phenyl [14C(U)]‐L‐asparagine, O‐acetyl [1‐14C]‐L‐serine, O‐benzoyl [7‐14C]‐L‐serine, benzyl[7‐14C]glycinate p‐toluenesulfonate, benzyl glycinate[1‐14C] p‐toluenesulfonate, and α‐dimethylaminoisobutyric acid[1‐14C].
Synthesis of 14C‐labelled polychlorobiphenyls derived from the labelled 4‐chloro‐, 2,5‐dichloro‐, 3,4‐dichloro‐, 2,3‐dichloro‐2,4,5‐trichloro‐ and 2,3,6‐trichloroanilines
Authors: Bergman Å. , Bamford I. , Wachtmeister C. A.
Published: October 2006

[14C] Aniline hydrogen sulphate was acetylated, and the acetanilide obtained was chlorinated with N‐chlorosuccinimide to 2‐chloro, 4‐chloro‐ and 2, 4‐dichloroacet[14C] anilide. The labelled 2‐ and 4‐chloroacet[14C] anilides were hydrolyzed and treated with aluminium chloride, hydrogen chloride and chlorine in dry dichloromethane to give the major products 2, 5‐dichloro‐ and 3, 4‐dichloro [14C] aniline. The labelled 2, 3‐dichloro‐ and 2,3, 6‐trichloroanilines were obtained as minor products from the chlorination of 2‐chloro [14C] aniline, likewise 2,4, 5‐trichloroaniline was obtained from 4‐chloro [14C] aniline. The [14C] anilines prepared were coupled with benzene, 1, 4‐dichloro‐, 1, 2‐dichloro or 1, 3‐dichlorobenzene to give 4‐chloro‐, 2, 3′,4′, 5‐tetrachloro‐, 2, 3, 3′, 4′ ‐ tetrachloro‐, 3,3′, 4,4′‐tetrachloro‐, 2, 2′, 5,5′‐tetrachloro‐, 2, 2′, 3,3′‐tetrachloro‐, 2, 2′, 3, 5′, 6‐pentachloro‐, 2, 2′, 4, 4′, 5‐pentachloro‐ and 2, 3′,4, 5, 5′‐pentachloro[14C]biphenyl.

3, 4‐Dichloro [14C] aniline and biphenyls prepared from this aniline were found to be contaminated by bromoanalogues. The origin of these have been studied.
No‐carrier‐added bromination of estrogens with chloramine‐t and Na77Br
Authors: Mazaitis J. K. , Francis B. E. , Eckelman W. C. , Gibson R. E. , Reba R. C. , Barnes J. W. , Bentley G. E. , Grant P. M. , O'Brien H. A.
Published: October 2006

The syntheses of monobromohexestrol and 17α‐bromoethynylestradiol are described as examples of bromination of phenolic and ethynyl moieties using Chloramine‐T. This technique represents a unique method of producing no‐carrier‐added radiobromoethynylderivatives. However, more efficient chromatography is needed to separate the chloroderivative, which is a side product of the reaction, from the radio‐bromoderivative.
Synthesis of 4‐fluoro‐2, 3‐dimethyl‐1‐phenyl‐3‐pyrazoline‐5‐one (4‐fluoroantipyrine) and 18f‐labeled analog by direct fluorination of antipyrine with molecular fluorine
Authors: Shiue C.‐Y. , Wolf A. P.
Published: October 2006

A facile procedure for preparing 4‐fluoroantipyrine is reported. Treatment of antipyrine with molecular fluorine gives 4‐fluoroantipyrine (3) and 4,4‐difluoro‐3‐hydroxy‐2,3‐dimethyl‐1‐phenylpyrazolidin‐5‐one (2). The product distribution depends on the ratio of antipyrine and molecular fluorine. The same procedure is used to prepare [18F]‐4‐fluoroantipyrine with high specific activity.
Synthesis of 14C‐labelled 2‐(p‐chloro‐α‐hydroxybenzyl)‐benzimidazole (HBBPC)
Authors: Durand A. , Beney C. , Duc C. Luu , Delord Cl. Agnius
Published: October 2006

p‐Chloro[14C]mandelic acid 2 was prepared from [14C]potassium cyanide and p‐chlorobenzaldehyde 1. The condensation of p‐chloro[14c] mandelic acid with 1,2‐diamino benzene 3 gave the title benzimidazole 4 labelled at the carbon atome 2 of the heterocyclic ring.
Synthesis of imipramine labelled with four deuterium atoms in 10, 11 positions
Authors: Chaudhuri Naba K. , Ball Thomas J.
Published: October 2006

The synthesis of imipramine labelled with four deuterium atoms in 10, 11 positions is described. The intermediate, trideutero‐o‐nitrotoluene was prepared by reduction of o‐nitrobenzoic acid with B2D6 followed by conversion of the resulting alcohol to the chloride and selective reduction of the chloride with NaBD4 in dimethyl sulfoxide. Trideutero‐o‐nitro‐toluene was then converted to tetradeutero‐2,2′‐dinitrodibenzyl by treatment with K‐tert butoxide in presence of air. The dinitro compound was reduced to a diamino compound which was then cyclized by heating its diphosphate salt, and the resulting amine on reaction with 1‐chloro‐3‐dimethylaminopropane gave tetradeuterated imipramine.
9α, 11α ‐tritiummarkierte östradiolderivate
Authors: Römer Johannes , Schwarz Sigfrid , Weber Gisela
Published: October 2006

In present work the syntheses of derivatives of 9α, 11α tritium labelled estradiols are described. Estron, estradiol, 17α‐ethynylestradiol and its 3‐isopropylsulfonyl ester were synthesized with high specific activity. Comparing the specific activities of all products it was obvious that tritium is exchanged in considerable amount in the strongly alkaline medium of ethynylation step. We believe that this exchange is attributed to tritium in benzylic positions.
Stablity upon storage, analysis and purification of 14C‐ and 3H‐labeled polycyclic aromatic hydrocarbons (PAH) and their metabolites
Authors: Susàn Alexander B. , Rohrig Timothy P. , Wiley James C.
Published: October 2006

The studies on the stability, analysis and purification of several 14C‐ and 3H‐labeled polycyclic aromatic hydrocarbons such as benzo[a]‐pyrene, benzo[e]pyrene, and dibenz[a,c]anthracene and their metabolites such as dihydrodiols, phenols, and tetrahydrodiol epoxides are reported.
Preparation of radioactively labelled indole‐3‐acetic acid precursors
Authors: Hofmann Frieder , Rausch Thomas , Hilgenberg Willy
Published: October 2006

A microscale method for the synthesis of indole‐3‐acetaldehyde, indole‐3‐ethanol, indole‐3‐acetaldoxime and indole‐3‐acetonitrile from radioactively labelled tryptophan with high yield and no reduction in specific radioactivity is described.
Production of carbon‐11 labelled methyl iodide by direct recoil synthesis
Authors: Wagner R. , Stöcklin G. , Schaack W.
Published: October 2006

A novel method for a one‐step on‐line production of no carrier added 11CH3I is described. The method makes use of recoil reactions of 11C‐atoms, produced via the 14N(p, α) 11C‐process in a gaseous N2‐HI flow target system. The radiochemical yield of 11CH3I under optimized conditions is 25 %. Separation from 11CH4 which is formed with a radiochemical yield of 45 % and from high boiling by‐products is readily achieved by washing and trapping procedures. Up to 90 mCi of pure 11CH3I have been produced with specific activities of about 300 Ci/mmol after a 40 minute collection time.
Tritiummarkierung Eines Neuen Steroids mit Fertilitätshemmenden Eigenschaften: 3‐methoxy‐14β, 15β‐methylen‐[9α, 11α‐3H]‐Östra‐1,3,5(10)‐trien‐17β‐OL
Authors: Wagner H. , Römer J. , Kasch H.
Published: October 2006

The synthesis of a [9α, 11α‐]‐tritium‐labelled new steroid with interceptive — post‐coital antifertility — activity, 3‐methoxy‐14β, 15β‐methylene‐estra‐1,3,5(10)‐triene‐17β‐ol, starting with the catalytic tritiation of 3‐methoxy‐estra‐1,3,5(10), 9(11)‐tetraene‐14α, 17β‐diol, is described.

3‐Methoxy‐14β, 15β‐methylene‐[9α, 11α‐3H]‐estra‐1,3,5(10)‐triene‐17β‐ol was obtained in a four‐step synthesis with high specific activity (3,8 Ci/mmole) and radiochemical purity better than 99 %. Radiolysis and storage conditions are examined.
Preparation of cis,cis‐, trans,cis‐, cis,trans‐ and trans,trans‐12,15‐octadecadienoic‐9,10‐d2 acids, methyl esters and triglycerides
Authors: Rakoff Henry , Emken Edward A.
Published: October 2006

Methyl cis,cis‐, trans,cis‐, cis,trans‐, and trans,trans‐12,15‐octadecadienoates‐9,10‐d2 were prepared by the Wittig Reaction between cis‐ or trans‐3‐hexenyltriphenylphosphonium bromide and methyl 12‐oxododecanoate‐9,10‐d2 with butyl lithium in ethyl ether. At room temperature, the Wittig Reaction gave a product mixture with 80‐85% cis geometry in the double bond formed. When the reaction was run at −40°C, followed by protonation with methanol and slow warm‐up to room temperature, the product mixture had 60‐65% trans geometry in the double bond generated. Mixtures of the cis,cis and trans,cis and of the cis,trans and trans,trans isomers were separated by partial silver resin chromatography, and the individual pure fatty esters were converted to the triglycerides through the respective acid chlorides. Melting points and nuclear magnetic resonance chemical shifts are presented.
Specific tritium labelling of thyroliberin on histidyl and prolyl residues
Authors: Levine‐Pinto H. , Morgat J. L. , Fromageot P.
Published: October 2006

Tritiation of thyroliberin (L‐(Glu‐L‐His‐L‐Pro‐NH2) starting from the L‐[Δ3‐Pro3]‐TRF, on prolyl and histidyl residues is being dealt with below.

By catalytic tritiation of the double bond, followed by iodination of histidyl residue and catalytic deshalogenation in presence of tritium gas, TRF was labelled with a specific radioactivity close to the theoretical value. 3H‐[2,5‐His2‐3,4‐Pro3]‐TRF retained all biological potencies.
Synthesis and evaluation of potential tumor localizing radiopharmaceuticals: Technetium‐99m iminodiacetic acid derivatives of sulfanilamides
Authors: Hunt F. C. , Maddalena D. J. , McLaren A. B. , Wilson J. G.
Published: October 2006

To exploit the tissue affinity of compounds for radiopharmaceutical purposes, attachment of chelating groups is usually necessary to facilitate technetium‐99m binding and transport.

The chelating group, iminodiacetic acid, previously used to modify lidocaine for hepatobiliary radiopharmaceuticals, was attached to several antibiotic sulfanilamides known to concentrate in certain transplanted animal tumors.

These iminodiacetic acid derivatives were labelled with technetium‐99m by the stannous chloride reduction method.

Biodistribution of the 99mTc labelled compounds in tumor bearing rats revealed no specific concentration in the tumors and localization mainly in the excretory organs.

The results indicate that, as in the case of lidocaine, conversion of the sulfanilamides into iminodiacetic acid derivatives and chelation with technetium leads to an altered biodistribution and loss of biological specificity.
Preparation of methadone and some congeners labeled with tritium in the aromatic rings
Authors: Kepler J. A. , Sparacino C. M. , Howe C. R. , Austin R. D.
Published: October 2006

[diphenyl‐2,2′‐3H2]Methadone with specific activity of 8‐30 Ci/mmol was prepared by reductive dehalogenation of 6‐dimethylamino‐4, 4‐bis(2‐chlorophenyl)‐3‐heptanone with carrier‐free tritium gas. The labeled congeners (−)‐α‐acetylmethadol, (−)‐α‐acetyl‐N‐normethadol, and (−)‐α‐acetyl‐N,N‐dinormethadol were prepared from (+)‐[diphenyl‐2,2′‐3H2]methadone.
Synthesis of n‐heptyltrichlorosilane 7‐13C for preparation of labeled chromatographic surfaces
Authors: Gangoda M. E. , Gilpin R. K.
Published: October 2006

This report describes the synthesis of carbon‐13 labeled n‐heptyltrichlorosilane from 13C methyl iodide. The product is labeled at the 7‐position of the alkyl chain in a 24% yield.
Tritiation of mianserin
Authors: Favier J. S. , Wallaart J. , Kaspersen F. M.
Published: October 2006

Labelling of mianserin in the N‐methyl group or the piperazine ring results in changes in the physical properties of the molecule. Using deuterium it is shown that mianserin can be labelled at metabolically stable positions without introducing isotope effects by exchange under alkaline conditions (at C10) or by reductive dechlorination (at C12 or C13).

[13‐3H]‐mianserin with a specific activity of 16 Ci. mmol−1 was synthesized by reductive dehalogenation of 13‐chloromianserin using 3H2. The position of the label was confirmed by 3H‐NMR spectroscopy.
Radiohalogenation of non activated aromatic compounds via aryltrimethylsilyl intermediates
Authors: Wilbur D. S. , Anderson K. W. , Stone W. E. , O'Brien H. A.
Published: October 2006

The utility of aryltrimethylsilyl derivatives to regiospecifically introduce carrier and no‐carrier‐added quantities of radiobromine and radioiodine into certain aromatic rings has been demonstrated. Using trimethylsilyltoluenes as a model system for aromatic rings that are not highly activated, conditions for the rapid and efficient incorporation of radiobromine and radioiodine were found. Reaction conditions necessary for the radiobrominations were very mild; however, the slower radioiodinations required elevated temperatures or highly acidic conditions.
Synthese de [14 C] ‐ sulfometuron methyle et de [14 C] ‐ metsulfuron methyle
Authors: Bastide Jean , Badon Robert
Published: October 2006

[[2‐14C] pyridimyl] sulfometuron methyl and [2‐14C) ‐ triazinyl] metsulfuron methyl, two sulfonylurea herbicides has been prepared by multistep synthesis. [2‐14C] 2‐amino‐4,6 dimethyl pyrimidine was obtained by two steps from [14C] guanidine and [2‐14C] 2‐amino‐4 methoxy‐4 methyl 1,3,5 triazine was obtained from [14C] cyanamide. The two herbicides were prepared by condensation of heterocycle with methyl‐2 (sulfonylisocyanate) benzoate.
Improved yields in the synthesis of 4‐nitro[1‐13C]aniline
Authors: Yilmaz (1) Ibrahim , Shine Henry J.
Published: October 2006

4‐Nitro[1‐13C]aniline has been prepared in overall yield of 54%, based on labeled acetone, by modification of a standard procedure (2).
Use of kinetic isotope effects in enzymatic oxidation of D‐[6‐3H]galactose for increasing its molar activity
Authors: Akulov G. P. , Korsakova N. A. , Kudelin B. K.
Published: October 2006

Large kinetic isotope effects have been observed in D‐[6‐3H]galactose enzymatic oxidation reactions catalyzed by the galactoseoxidase. It is possible to use these effects for considerable increase of the molar activity of D‐galactose labelled with tritium in the position 6.
Aryltrimethylammonium trifluoromethanesulfonates as precursors to aryl [18F]fluorides: Improved synthesis of [18F]GBR‐13119
Authors: Haka Michael S. , Kilbourn Michael R. , Leonard Watkins G. , Toorongian Steven A.
Published: October 2006

Aromatic nucleophilic substitution of various trimethylammonium trifluoromethanesulfonates with [18F]fluoride has been evaluated. Fluorinations were studied over a temperature range of 45–165°C, with decay corrected yields ranging from 20–80%. [18F]GBR 13119, 1‐[2‐{(4‐[18F]fluorophenyl)(phenyl)methoxy}ethyl]‐4‐(3‐phenylpropyl)piperazine, a potential radio‐tracer for the dopamine uptake system, has been prepared in no‐carrier‐added form from 4‐N,N,N,‐trimethylaniliniumphenylmethanone trifluoromethanesulfonate. Purification by solid‐phase techniques yielded the product in 20% decay corrected radiochemical yield and >98% radiochemical and chemical purity without HPLC.
Synthesis of tritium‐labelled enantiomers of myo‐inositol 1,4,5‐trisphosphate
Authors: Marecek James F. , Prestwich Glenn D.
Published: October 2006

Both natural D‐ and L‐enantiomers of myo‐Ins(1,4,5)P3 were synthesized with specific activities 14–16 Ci/mmol. A suitable inositol derivative was resolved as the diastereomeric camphanate esters, and the chiral inositol derivatives were oxidized to the protected inosose. Reduction of each chiral ketone with sodium borotritide and manipulation of protecting groups gave the enantiomeric [1‐3H]‐2,3,6‐tri‐0‐benzyl‐myo‐inositols in 55% radiochemical yield. Phosphorylation with tetrabenzylpyrophosphate and complete hydrogenolytic debenzylation provided the separate D‐myo and L‐myo‐ [1‐3H]‐Ins(1,4,5)P3 enantiomers in 30% radiochemical yield.
A method for the preparation of labelled gossypol by the incorporation of 14C acetate
Authors: Guadalupe Rojas M. , Stipanovic Robert D. , Williams Howard J. , Vinson Bradleigh
Published: October 2006

Carbon‐14 14labelled gossypol has been prepared by incorporating 1,2‐14C acetate in the growth medium of cold shocked cotton (Gossypium arboreum) seedling roots. Unlabelled gossypol was added during the purification procedure to aid crystallization; thus, from 350 seedling roots, 25 uCi sodium (1,2‐14C) (45–60 mCi/mmol) acetate and 800 mg of unlabelled gossypol; 350 mg of labelled gossypol (1900 dpm/mg) was isolated.
Determination of isotopic purity and position in deuterated methyl behenate
Authors: Liu R. H. , Bailey A. V.
Published: October 2006

In the course of preparing peanut oil type triglycerides for metabolism studies, methyl esters of deuterated behenic acid, a saturated 22‐carbon fatty acid, with zero, two, and six deuterium atoms were synthesized. The specific positions of deuterium atoms and the completion of deuteration in the products were characterized by gas chromatography/mass spectrometry methods.
A convenient synthesis of deuterated leukotriene A4 methyl ester
Authors: Bestmann Hans Jürgen , Meese Claus O. , Röder Thomas
Published: October 2006

2,2,3,3‐[2H4]‐1‐Iodopentane (8b) was prepared in four steps from propargyl alcohol and used in the C‐alkylation of the THP‐protected 3‐butyne‐1‐ol (10). Subsequent protective group removal of 11b, semi‐deuteration of the acetylenic alcohol 12b, and further transformation by known methods afforded the labelled key reagent 3,4,6,6,7,7‐[2H6]‐(Z)‐(3‐nonen‐1‐yl)triphenylphosphonium iodide (3b). Wittig olefination of epoxy dienal 2 with the ylide generated from 3b completed the convenient synthesis of hexadeuterated leukotriene A4 methyl ester (1b).
Synthesis of carbon‐14 labeled PD 117,302 and PD 126,212, potential new analgesic agents
Authors: Hays Sheryl J. , Hicks James L. , Butler Donald E. , Huang C. C.
Published: October 2006

Two kappa opiate agonists 1 and 2 have been labeled from bromo‐[1‐14C]‐acetic acid and sodium [1‐14C]acetate respectively.
Labelled compounds of interest as antitumour agents. Part II (1). Synthesis of 2H and 3H isotopomers of RSU 1069 and Ro 03‐8799 (pimonidazole)
Authors: Webb Paul , Threadgill Michael D.
Published: October 2006

2H‐ and 3H‐Labelled RSU 1069 and Ro 03‐8799 (pimonidazole) have been synthesised by reduction of 1‐(3‐chloro‐2‐oxopropyl)‐2‐nitroimidazole with the appropriately labelled sodium borohydride, followed by ring‐closure of the chlorohydrins and treatment of the resulting epoxides with aziridine or piperidine. In both cases, the specific activities were 200 mCi mmol−1 and the radiochemical yields were 86%. The parent compounds are radiosensitisers of hypoxic tumour cells.
Synthesis of [5‐14C]pentostatin, an antileukemic agent and potent adenosine deaminase inhibitor
Authors: Woo Peter W. K. , Lee Helen T.
Published: October 2006

Reaction of triethyl ortho[14C]formate (2) with 2‐amino‐1‐(5‐amino‐1H‐imidazol‐4‐yl)ethanone dihydrochloride (1) in the presence of molecular sieves 4A gave 6,7‐dihydro[5‐14C]imidazo[4,5‐d][1,3]diazepin‐8(3H)‐one hydrochloride monodimethyl sulfoxide (3) (radiochemical yield, 60%). The latter was persilylated with bis(trimethylsilyl)trifluroacetamide (4) and glycosylated with 2‐deoxy‐3,5‐di‐O‐p‐toluoyl‐α‐D‐erythro‐pentofuranosyl chloride (6) to give a mixture from which the 3‐N‐β‐glycosylated product 8 was isolated by chromatography and crystallization (13%). Deprotective saponification with methanolic sodium methoxide and subsequent sodium borohydride reduction of the 8‐keto function gave a (R,S)‐mixture from which the desired (R)‐isomer, [5‐14C]pentostatin (11), was isolated by preparative HPLC over a C18 column, desalting with Diaion‐HP20, and subsequent crystallization (39%).