bluuebunny/crossref_metadata_2025_split huggingface dataset:
Labelling of a new hypolipaemic agent with carbon‐14, preparation of 1,1‐bis[4‐(1‐carboxy‐1‐methylpropoxy)phenyl]cyclohexane‐2‐14C
Authors: Yoshitake Akira , Makari Yoshiaki , Kawahara Kazuo , Doi Tadashi 
Published: October 2006

Abstract1,1‐Bis[4‐(1‐carboxy‐l‐methylpropoxy)phenyl]cyclahexane (S‐8527) (I), a new hypolipaemic agent, was labelled at C‐2 with carbon‐14 for the use of metabolic studies. The procedure used is illustrated in Fig. 1. Cyclohexane‐2‐14C which was prepared from potassium cyanide‐14C was condensed with phenol to afford 1,1‐bis(4‐hydroxyphenyl)cyclohexane‐2‐14c (VI). Condensation of VI with ethyl methyl ketone and chloroform under a strong base (potassium hydroxide) gave S‐8527‐2‐14C (I). A total of 3.11 mCi of pure S‐8527‐2‐14C (I) was obtained, representing 12% radiochemical yield from potassium cyanide‐14C. Furthermore, a new radioactive by‐product was isolated and elucidated its structure as X (Fig. 3).
Synthesis of high specific activity benzo[a]pyrene‐6‐t and its K‐region oxidized derivatives
Authors: Harvey Ronald G. , Fu Peter P. 
Published: October 2006

AbstractThe potent carcinogen benzo[a]pyrene specifically tritiated in the 6‐position was synthesized through hydrogenation of 6‐bromobenzo[a]pyrene with tritium gas. The benzo[a]pyrene‐6‐t was then employed in the synthesis of benzo[a]pyrene‐6‐t 4,5‐oxide of high specific activity via. the corresponding cis‐diol, quinone and trans‐diol. Also, BaP‐6‐d and BaP‐G‐t were employed in the synthesis of the corresponding K‐region oxidized derivatives (cis‐ and trans‐diols, quinones, and oxides). Loss of the isotopic label was generally minimal except in the transformations involving the high specific activity BaP‐6‐t compounds.
Carbon‐14 ring labelling of some methylxanthines of pharmacological importance
Authors: Ayrey G. , Yeomans M. A. 
Published: October 2006

AbstractPreparative, separative and analytical methods are described for the following labelled compounds: 4‐amino[5‐14C] formamidouracil (II), 1,3‐dimethyl‐4‐amino[5‐14C]formamidouracil (III), 1,3‐dimethyl[S‐14c]xanthine ([8‐14C]theophylline) (IV), 1,3,7‐trimethyl [8‐14C]xanthine ([8‐14C]caffeine) (V), 4‐amino[2‐14C]uracil (VI),′ 4‐amino‐5‐nitroso[2‐14C]uracil (VII), 4,5‐diamino[2‐14C]uracil (VIII), [2‐14C]xanthine (IX), 3‐methyl[2‐14C]xanthine (X), [2‐14C]theobromine (XI), [2‐14c]theophylline (XII) and [2‐14c]caffeine (XIII).
Tritium labelling of ribonuclease by the gas‐exposure method, as improved by an electric discharge
Authors: Noyer M. , Schnek A. G. , Léonis J. , Winand M. 
Published: October 2006

AbstractWhen lyophilized samples of bovine pancreatic ribonuclease are exposed to tritium gas, the exchange process can be markedly improved by applying high frequency electric discharges.Labelling has been carried out for 5, 15 or 30 minutes periods. Labile radioactivity, was then removed by means of molecular sieving and repeated lyophilizations, the tritiated protein being submitted to further purification by ion‐exchange chromatography.The specific radioactivity of such purified samples is in the Curie/mmole range, and the biological activity of the enzyme remains well preserved. The distribution of tritium atoms among component aminoacids has been determined, after acid hydrolysis of the labelled protein.
Synthesis of carbon‐13 labelled 6‐substituted benzo (a) pyrenes
Authors: Royer Robert E. , Daub Guido H. , Jagt David L. Vander 
Published: October 2006

AbstractSodium formate‐13C, prepared by hydrolysis of isopropyl formate, was allowed to react with N‐methylaniline hydrochloride to prepare the formylating agent N‐methylformanilide‐1‐13C. Formylation of benzo(a)pyrene with N‐methylformanilide‐1‐13C gave the 6‐13CHO derivative which was reduced to 6‐13CH3 and 6‐13CH2OH benzo(a)pyrenes. 6‐13CH2C1 benzo(a)pyrene was prepared from the 6‐13CH2OH derivative.
Synthesis of tritium labeled mazindol
Authors: Dugger Harry A. , Tabot Kenrick C. 
Published: October 2006

AbstractMazindol was labeled with tritium in the 6,9 positions in low yield starting with dimethyl phthalate‐3,6‐3H which was prepared by reduction of dimethyl 3‐chlorophthalate with tritium gas using 10% palladium on charcoal as a catalyst. The labeled dimethyl phathalate was hydrolisized with extensive loss of the label by exchange and after conversion to phthalic anhydride was condensed with chlorobenzene to give 2‐(p‐chlorobenzoyl) benzoic acid‐3,6‐3H. This acid was converted in two steps into 5‐hyddroxy‐54‐imidazo [2,1‐a] isoindol‐6,9‐3H (mazindol‐6,9‐3H). In a similar fashion, mazindol‐7,8‐3H was prepared in higher yields beginning with dimethyl 4‐chlorophthalate. There was no loss of the label during the hydrolysis of dimethyl Phthalate‐4,5‐3H.
Synthese d'un diuretique marque au carbone 14: Acide dichloro‐2,3 [thenoyl‐2 (14C = 0)]‐4 phenoxy acetique (D.C.I. acide tiénilique)
Authors: Herbert M. , Pichat L. 
Published: October 2006

Abstract2‐Thenoic acid (14C = 0) 1 is prepared in 75 % radioactive yield by carbonation with 14CO2 of 2‐thienyL‐magnesium bromide. Boiling of 1 with oxalyl chloride gives rise to 2‐thenoylchloride (14CO) which is not isolated and is condensed with 2,3 dichLoroanisoLe under FrieLdeL‐Grafts conditions. Ketone 3 is demeth Lated with AlCl3 in benzene to give rise to 4‐ 2‐thenoyl (14C = O)‐2,3‐dichloro phenol 4. The sodium derivative of 4 is condensed in D.M.F. with sodium chloracetate to Lead to the title compound with an overall yield of 16 % based on 14CO2 – TieniLic acid‐14c, specific activity: 50 mCi/mMole, has been found to be sensitive to self‐irra‐diation decomposition in the dry state at ‐ 25%° C. Radiation decomposition is minimized at 24 mCi/mMole in methanol solution.
Preparatton and high pressure liquid chromatography of 5‐astatouracil
Authors: Meyer G.‐J. , Rössler K. , Stöcklin G. 
Published: October 2006

Abstract5‐astatouracil was prepared via the decomposition of the 5‐diazonium salt of uracil in the presence of 211At− with overall yields ranging from 20 to 30%. Identification and separation was carried out on four different high pressure liquid chromatography columns. Under identical conditions, astatination is more effective than iodination, and complex formation of halide with the diazonium compound seems to be the product forming mechanism.
Synthesis of pentachloronitrobenzene‐14C6
Authors: Kadunce R. E. , Lamoureux G. L. 
Published: October 2006

AbstractPentachloronitrobenzene‐14C6 was synthesized in 81.7% yield by exhaustive chlorination of nitrobenzene‐14C6. Hexachlorobenzene‐14C6 was produced in 11% yield as a byproduct of the reaction.
Preparation de l'acide biphenyl‐4, oxo‐4, methylene‐2 butyrique (14C‐4) et de deux derives chloro substitues
Authors: Cousse Henri , Bonnaud Bernard , Pichat Louis , Aubert Francis 
Published: October 2006

AbstractItaconic acid‐4‐14C has been prepared by condensation of sodium cyanide 14C with ethyl α‐bromomethyl acrylate and hydrolysis of the intermediate ethyl α‐(cyanomethyl) acrylate.Itaconic anhydride‐4‐14C has been used in Friedel‐Crafts reactions with respectively biphenyl, 2‐chlorobiphenyl, 4‐chlorobiphenyl for the preparation of 4‐biphenyl‐4‐oxo‐2‐methylene butyric acid‐4‐14C and the corresponding‐2′chloro and 4′‐chloro substituted derivatives.
Synthesis of 1‐phenyl‐2‐phenyl‐1‐13C‐ethene‐1‐13C (trans‐stilbene) and derivatives
Authors: Braden Gary A. , Hollstein Ulrich 
Published: October 2006

AbstractFor mass spectrometric studies 1‐phenyl‐2‐phenyl‐1‐13C‐ethene‐1‐13C (trans‐stilbene) was synthesized from acetic‐1‐13C acid and acetic‐2‐13C acid via methylcyclohexene‐1‐13C and ‐α‐13C and toluene‐1‐13C and ‐α‐13C. No scrambling of the label was observed during the aromatization step. The labeled stilbene was converted into 1‐phenyl‐2‐phenyl‐1‐13C‐ethane‐1‐13C (bibenzyl), 2‐phenyl‐3‐phenyl‐1‐13C‐oxirane‐2‐13C (trans‐stilbene oxide), meso‐1,2‐dibromo‐1‐phenyl‐2‐phenyl‐1‐13C‐ethane‐1‐13C and 1‐phenyl‐2‐phenyl‐1‐13C‐ethyne‐1‐13C (tolan).
The preparation of deuterium‐ and tritium‐labeled pirbuterol hydrochloride
Authors: McIlhenny Hugh M. 
Published: October 2006

AbstractA mild exchange labeling procedure utilizing O‐deuterated or O‐tritiated t‐butanol with sodium catalysis afforded isotope exchange in the α‐hydrogen position of the amide N‐t‐butyl‐2‐(5‐benzyloxy‐6‐hydroxymethyl‐2‐pyridyl)‐2‐hydroxy‐acetamide, thereby extending the utility of this approach with ketones to poor enolizers that are base labile. Complete label retention accompanied the subsequent steps of reduction and debenzylation to 2‐hydroxymethyl‐3‐hydroxy‐6(l‐hydroxy‐2‐t‐butylaminoethyl)‐pyridine dihydrochloride (pirbuterol hydrochloride)‐2H or ‐3H, in 15‐18% overall yield at the 4 mmole level. Deuterium incorporation was estimated to be 39%; a specific activity of 206 μc/mg was achieved by radiolabeling. A radiochemical and chemical purity of > 99.5% was established. Tritium label stability was demonstrated in aqueous media at acidic, neutral and basic pH.
Preparation of chloroacetaldehyde‐l‐14C and its reaction with adenine and cytosine nucleotides
Authors: Greenfield John C. , Leonard Nelson J. , Nystrom Robert F. 
Published: October 2006

AbstractChloroacetaldehyde, which reacts selectively with cytosine and adenine nucleotides to give fluorescent etheno‐bridged derivatives, was synthesized bearing a 14C label. The chloroacetaldehyde l‐14C, prepared from glycerol‐2‐14C, was used to form etheno‐bridged adenine and cytosine nucleotides for enzyme studies and was applied to the chemical modification of tRNA.
Synthesis and properties of dodecane‐1,12‐13C2 and dodecane‐1,1,1,12,12,12‐2H6
Authors: Shaw G. J. , Milne G. W. A. 
Published: October 2006

AbstractNormal dodecane labeled with either carbon‐13 or deuterium at both the terminal methyl groups has been synthesized. The mass spectra and PNMR and CNMR spectra of these compounds have been measured and are reported.
Spezifische 15N‐markierung von creatinin
Authors: Medina R. , Schmidt H.‐L. 
Published: October 2006

AbstractBy reaction of 1‐methyl‐2‐methylthio‐2‐imidazoline‐4‐on‐hydroiodide (2) with ammonia‐[15N], creatinine‐[15NH2] is synthesised in a one step reaction giving an 80% yield on the mmol scale. The specificity of labelling in the amino group is proved by enzymatic hydrolysis and examination of the reaction products by mass spectrometry.
Synthese du safrole marque au carbone 14 dans la chaine allylique: safrole 14C‐1′
Authors: Pichat L. , Tostain J. 
Published: October 2006

AbstractCarbonation of 3,4 methylenedioxy phenylmagnesium bromide with 14CO2 leads to (carboxyl 14C) 3,4 methylenedioxy benzoic acid. Reduction of the latter with LiAlH4 in T H FTHF: Tetrahydrofurne; CPV: Chromatographie en phase vapeur; CCM: Chromatographie sur couche mince.
gives rise to 3,4 methylenedioxy benzyl alcohol which reacts with thionylchloride to provide the corresponding chloride. By action of magnesium in T H F 3‐4 methylenedioxy benzylmagnesium chloride is obtained; it is then condensed with vinyl bromide in presence of catalytic quantities of FeCl3 to give (1′‐14C) safrol, specific activity: 15 mCi/mMole with an overall yield of 40 % based on barium carbonate.
The synthesis of tritium labeled cardioselectlve beta‐adrenoceptor antagonists
Authors: G. Shtacher , M. Erez , S. Cohen , A. Cohen , O. Buchman 
Published: October 2006

AbstractTwo cardioselective beta‐adrenoceptor antagonists: dl‐acetanalide‐4′‐[3‐(isopropylamino)‐2‐hydroxypropoxy] (“practolol”), and dl‐chloroacetanilide‐4′‐[3‐(isopropylamino) ‐2‐hydroxypropoxy] (“chloropractolol”), labeled with tritium at positions 3′ and 5′of the aromatic ring were prepared. The starting 3 materials for the synthesis of the aryloxypropanolamines was 2,6‐di‐ 3H‐4‐acetamido phenol, prepared by catalytic dehalogenation of 2,6‐dibromo‐4‐acetamido‐phenol, employing tritium gas. Condensation of 2,6‐di‐3H‐4‐acetamido‐phenol with epichlorohydrin, followed by epoxide ring opening with isopropylamine yielded 3′ 5′‐di‐3H‐acetanilide‐4′‐[3‐(isopropylamino)‐2‐hydroxypropoxy], (3′,5′‐di‐ 3H‐ practolol). Deacetylation of 3′,5′‐di‐3H‐practolol followed by selective ar‐N chloroacetylation of the resulting 1‐(2′,6′‐di‐3H‐4‐amino)‐phenoxy‐3‐isopropylaminopropan‐2‐ol, gave 3′,5′‐di‐3H‐chloropractolol with a specific activity of 750 mCi/mmol.
Labelled compounds of potential biological interest. IV. Tritium labelling of some cyclzing compounds
Authors: Gosztonyi Tamas , Domeij Karl Erik , Ross Svante 
Published: October 2006

AbstractQuaternary ammonium compounds formed at the site of action by spontaneous cyclization of tertiary ω‐haloalkylamine precursors may have interesting pharmacological properties. In order to study the pharmacokinetics of the cyclization principle, a series of new tertiary ω‐haloalkylamines derived from p‐chloroamphetamine has been synthesized both unlabelled and labelled with tritium at high specific activity.
An efficient synthesis of [2‐13C]‐monobromoacetic acid
Authors: Climie I. J. G. , Evans D. A. 
Published: October 2006

Abstract[2‐13C]‐Monobromoacetic acid was prepared in good yield by the bromination of acetic acid in the presence of phosphorous trichloride by appropriate modification of the method of Marvel.(1) A by‐product of this method was found to be bromoacetyl bromide, which could be avoided by hydrolysis to the required product by a modified work‐up procedure. Pure monobromoacetic acid was obtained by sublimation.
Labelled organophosphorus pesticides. II. Synthesis of carbon‐14 labelled N‐sec‐butyl O‐ethyl O‐(5‐methyl–2‐nitrophenyl) phosphoramidothioate (cremart®)
Authors: Yoshitake Akira , Shono Fumiaki , Kamada Takeshi , Nakatsuka Iwao 
Published: October 2006

AbstractN‐sec‐Butyl O‐ethyl O‐(5‐methyl–2‐nitrophenyl) phosphoramidothioate (Cremart) (I), an organophosphorus herbicide, was labelled with carbon‐14 at the aryl methyl group for metabolic studies. The synthetic procedures are shown in Fig. 1. 1‐Methoxy‐3‐methyl‐14C‐benzene was nitrated with fuming nitric acid‐acetic anhydride to give 2‐methoxy‐4‐methyl‐14C‐1‐nitrobenzene which on O‐demethylation with boron tribromide gave 5‐methyl‐14C‐2‐nitrophenol. Condensation of the latter with N‐sec‐butyl O‐ethyl phosphoramidochloridothioate in the presence of potassium carbonate afforded Cremart‐(aryl methyl‐14C)(I) in the overall yield of 9.2% from methanol‐14C, which had a specifie activity of 5.96 mCi/mmole.
A synthesis of camphene‐8‐14C and toxaphene‐14C
Authors: Oliver James E. 
Published: October 2006

AbstractAn efficient one‐vessel synthesis of camphene‐8–14C was developed. Methyl‐14C iodide was reacted with triphenylphosphine; treatment of the resulting phosphonium salt with methyllithium produced methylene[‐14C]‐triphenylphosphorane, which was condensed with camphenilone to provide camphene‐8–14C. Chlorination of the latter compound produced toxaphene‐14C, an important polychlorinated insecticide.
Tritium distribution, enantiomer formation, and glycine production in L‐valine labeled by microwave discharge activation of tritium gas
Authors: Ehrenkaufer Richard Lee E. , Wolf Alfred P. , Hembree Wylie C. , Lieberman Seymour 
Published: October 2006

AbstractThe labeling of L‐valine by microwave discharge activation of tritium gas was found to be general (i.e., all positions were labeled) but non‐random in distribution. The α, β, and γ positions contained 7.1%, 32.7% and 60.2% respectively. On a per‐hydrogen basis the β‐position was favored by more than a factor of 3, whereas the chiral α‐position was the least labeled. Net retention of the L‐configuration was observed at the chiral center with only 1.56% D‐valine being formed. Small amounts of glycine were found to be produced by fragmentation of the alkyl side chain of valine.
Synthesis of 14C‐labelled compounds. I. Synthesis of 2 (14C)‐dinitrosohexahydropyrimidine
Authors: Brann Horst , Bertram Barbara , Wiessler Manfred 
Published: October 2006

AbstractA convenient procedure to synthesize 2–14C‐dinitroso‐hexahydropyrimidine (DNHP) is described. The synthesis begines with the condensation of 14C‐formaldehyde and propylenediamine‐1,3 in benzene with azeotropic removal of water. The resulting bases are isolated from the reaction mixture as hydrochlorides and are nitrosated with sodium nitrite in aqueous medium at a constant pH of 4 to 5. After column chromatography on Silica gel and recrystallisation from ether 2–14C‐dinitroso‐hexahydropyrimidine (DNHP) is isolated in 30.7% yield based on 14C‐fomaldehyde.
Synthesis of 14C‐labelled compounds. II. Synthesis of 14C‐methylacetoxy methylnitrosamine
Authors: Braun Horst , Wiessler Manfred 
Published: October 2006

Abstract1,3,5–14C‐trimethylhexahydro‐1,3,5‐triazine was prepared by condensing 14C‐methylamine‐hydrochloride and formaldehyde in a concentrated aqueous solution. The so formed triazine reacts with Nitrosylchloride at 0°C to 14C‐methylchlorarethylnitrosamine which was not isolated and reacted further with silver acetate. After column chromatography on Silica gel and distillation 14C‐methylacetoxymethylnitrosamine was obtained in a 24.1% yield based on 14C‐methylamine‐hydrochloride.
Preparation du butyne‐2(D6) par isomerisation ET echange DU butyne‐1; dosages isotopiques
Authors: Saussey J. , Lavalley J. C. , Janin A. , Vallet Et A. 
Published: October 2006

AbstractA convenient method for the synthesis of perdeuterated 2‐butyne has been elaborated. By shaking 1‐butyne at 180°C for 3 days with a base (LiOD in D2O) it has been shown, together with isomerization of the hydrocarbon with migration of the triple bond, there was hydrogen exahange. Four exahanges gave CD3C°CCD3, with high isotopia purity (τ = 99,5 %). Results of an experiment under lower temperature aonfirmed the mechanism. Different methods of isotopic analysis have been used, in particular 1H and 13C NMR and analytical gas chromatography.
Synthesis of nornicotine‐2,4,5,6‐d4 and its N′‐nitroso derivative
Authors: Munson James W. , Hodgkins Thomas G. 
Published: October 2006

AbstractNornicotine‐2,4,5,6‐d4 and its N′‐nitroso derivative were synthesized from pyridine‐d5. Initially, pyridine‐d5 was brominated in fuming D2SO4 to give 3‐bromopyridine‐d4. Treatment of this material with n‐butyllithium and dry ice followed by acidification gave nicotinic acid‐2,4,5,6‐d4. Conversion of this substance to the acid chloride hydrochloride (via thionyl chloride) followed by treatment with absolute ethanol gave ethyl nicotinate‐2,4,5,6‐d4. The ester was condensed with N‐trimethylsilyl‐2‐pyrrolidinone in the presence of n‐butyllithium and diisopropylamine to give, after hydrolysis and decarboxylation, myosmine‐2,4,5,6‐d4. Reduction of this material with sodium borohydride gave nornicotine‐2,4,5,6‐d4. Conversion to the N′nitroso derivative was achieved by treatment with nitrous acid.
Improved syntheses of carbon‐14 labelled 3‐phenoxybenzyl [1R,cis]‐ and [lR,trans]‐3–(2,2–dichlorovinyl)‐2,2‐dimethylcyclopropanecarboxylates
Authors: Nakatsuka Iwao , Shono Fumiaki , Yoshitake Akira 
Published: October 2006

Abstract3‐Phenoxybenzyl [1R,cis]‐3–2(2,2‐dichlorovinyl)‐2,2‐dimethyl‐cyclopropanecarboxylate (I) and its [1R,trans]‐isomer (II) were labelled with carbon‐14 at C‐2 position of the dichlorovinyl side chain for metabolic studies. The stereospecific syntheses were achieved according to the reaction scheme shown in Fig. 1. Wittig reaction of methyl [1R,cis]‐3‐formyl‐2,2‐dimethylcyclo‐propanecarboxylate with carbon‐14C tetrachloride followed by hydrolysis gave [1R,cis]‐3‐(2,2‐dichlorovinyl‐2–14C)‐2,2‐dimethylcyclopropanecarboxylic acid (VIa). Chlorination of the acid (VIa) and subsequent treatment of the resulting acid chloride with 3‐phenoxybenzyl alcohol afforded 3‐phenoxybenzyl [1R,cis]‐3–(2,2‐dichlorovinyl–2‐14C)‐2,2‐dimethylcyclopropane‐carboxylate (I) in the overall yield of 33%. Its [1R,trans]‐isomer (II) was also prepared in 35% yield by the similar procedures. The specific activities of I and II were 4.30 and 3.80 mCi/mmole respectively.
Preparation and characterisation of tritiated derivates of galactosylceramide and glucosylceramide
Authors: Poulos A. , Pollard Ac 
Published: October 2006

AbstractRadiolabelled glucosylceramide and galactosylceramide have been prepared by the catalytic tritiation of a mixture of the corresponding unlabelled sphingolipids, and purified by preparative thin‐layer chromatography. The localisation of the label was determined by degrading the individual monohexosyl ceramides with aqueous methanolic hydrochloric acid and measuring the radioactivity content of the liberated fragments. Under the particular experimental conditions described, more than 98% of incorporated tritium was found in the ceramide portion of each sphingolipid, while the greater part (> 80%) of this radioactivity was detected in the long‐chain fatty acid moieties.The method offers a convenient means of preparing labelled substrates suitable foruse in metabolic studies. The data suggest that to reduce costs, mixtures rather than individual sphingolipids, can be tritiated.
Synthesis of labelled bioactive compounds. III. 2‐(arylimino)‐imidazolidine labeled with 14C, tritium and deuterium
Authors: Stiasni M. , Stähle H. 
Published: October 2006

AbstractFive compounds of a group of 2‐(arylimino)‐imidazolidines, among them Clonidine (St 155), have been labeled with 14 in the following manner: Potassium cyanide‐[14C] was converted to potassium thiocyanate‐[14C] and subsequently to the N′‐phenylthiourea using benzoyl chloride and the corresponding aniline. The thiourea was saponified and reacted with methyl iodide to give the quaternary isothiourea derivative. Ring closure to the imidazolidine was achieved through condensation with ethylenediamine. ‐ Tritium labeled Clonidine was obtained by catalytic debromination of the 4‐bromoderivative with tritium gas. ‐ The starting material for deuteroclonidine was ethylene‐[2H4]‐diammonium dichloride.
The synthesis of [3H] and [14C]o‐chlorobenzylidenemalononitrile (CS)
Authors: Harrison J. M. , Inch T. D. , Lawston I. W. , Ley R. V. , Sainsbury G. L. 
Published: October 2006

AbstractUsing similar procedures, the syntheses of [2‐14C]‐malononitrile and malono [14C]nitrile are described. Condensation with o‐chlorobenzaldehyde affords [2‐14C]‐o‐chlorobenzylidenemalononitrile and o‐chlorobenzylidenemalono [14C]nitrile respectively. The syntheses of [3H]o‐chlorobenzaldehyde and o‐chlorobenz[14C]aldehyde, again by a common sequence of reactions, is described and with malononitrile gives [3H]‐o‐chlorobenzylidenemalononitrile and [1‐14C]‐o‐chlorobenzylidenemalononitrile.
Biosynthetic preparation of diethylstilbestrol monoglucuronide – (glucuronyl‐U‐14C)
Authors: Corbett M. D. , Duncan W. P. , Chipko B. R. , Cahoy J. E. 
Published: October 2006

AbstractThe production of diethylstilbestrol monoglucuronide – (glucuronyl‐U‐14C) by incubation of uridine diphospho‐D‐ glucuronic acid‐U‐14C with diethylstilbestrol in the presence of guinea pig liver microsomes is described. The specific activity of the product was 9.1 mCi/mmole and the overall radiochemical yield was 13%, based on UDPGA – (glucuronyl‐U‐14C).
Preparation of tritium‐labeled compounds. VI. Nafoxidine hydrochloride by clemmensen reduction and by solvent exchange of intermediates
Authors: Thomas Richard C. , Lednicer Daniel 
Published: October 2006

AbstractTritium‐labeled nafoxidine hydrochloride, 1‐{p‐[2‐(N‐pyrro‐lidino) ethoxy]phenyl}‐3,4‐dihydro‐6‐methoxy‐2‐phenylnaphthalene hydrochloride (I), having two different intramolecular distributions of tritium, was prepared from 6‐methoxy‐2‐phenyl‐1‐tetralone (IV). I was labeled in the 4 position by incorporation of IV which had been labeled in the 4 position by Clemmensen reduction of 2‐phenyl‐4‐(m‐methoxyphenyl)‐4‐ketobutyric acid (II) in the presence of tritiated water, followed by cyclization of the resulting 2‐phenyl‐4‐(m‐methoxyphenyl) butyric acid (III). I was labeled in the aromatic positions of its phenylnapthalene moiety at a higher specific activity by incorporation of IV which had been generally labeled by exchange with tritiated trifluoroacetic acid.