bluuebunny/crossref_metadata_2025_split huggingface dataset:
Stereospecific synthesis of L‐[1,4‐13C2]aspartic acid, L‐β‐([13C]cyano)alanine and L‐[4‐13C]aspartic acid
Authors: Röhm Klaus H. , van Etten Robert L. 
Published: October 2006

AbstractA convenient stereospecific synthesis of L‐aspartic acid, 13C‐labelled in both carboxyls, is described. The crucial step of the procedure is the conversion of [1,4‐13C2]fumaric acid to L‐aspartic acid utilizing the enzyme L‐aspartase. In addition, an improved synthesis of L‐β([13C]cyano)alanine was developed. This compound is easily converted to L‐[4‐13C]aspartic acid.
Preparation of [4‐3H]‐3‐dehydroretinol by sodium borotritide reduction
Authors: Tosukhowong Pichit , Supasiri Thararat 
Published: October 2006

Abstract[4‐3H]‐Dehydroretinol (5) was prepared from a vitamin A derivative. The procedure involves conversion of methyl retinoate (1) to methyl 4‐oxoretinoate (2) by manganes dioxide oxidation. The 3H‐label was introduced by sodium borotritide reduction of methyl 4‐oxoretinoate (2) followed by acid catalyzed dehyration to methyl [4‐3H]‐3‐dehydroretinoate (4). Reduction of the tritiated methyl dehydroretinoate with lithium aluminium hydride yielded [4‐3H]‐3‐dehydroretinol (5). Final purification was achieved by preparative thin layer chromatography.
Preparation of 14C‐ and 18O‐labeled 2‐[2‐methoxy‐4‐(methylsulfinyl)phenyl]‐1H‐imidazo[4,5‐c]‐pyridine hydrochloride (LY175326), a cardiotonic with inotropic and vasodilator activities
Authors: Kau Don , Krushinski Joseph H. , Robertson David W. 
Published: October 2006

AbstractTwo different forms of 14C‐labeled 2‐methoxy‐4‐(methylthio) benzoic acid were prepared and employed in the synthesis of 14C‐labeled 2‐[2‐methoxy‐4‐(methylsulfinylphenyl]‐lH‐imidazo‐[4,5‐c]pyridine hydrochloride (LY175326), a cardiotonic with inotropic and vasodilator activities that is currently in clinical trials. The synthetic procedures described in this report allowed the introduction of the 14C‐label in the antepenultimate step. Additionally, an 18O‐labeled form of LY175326 was synthesized to facilitate kinetic analysis of the formation of its sulfide and sulfone metabolites.
Synthesis of 6‐(10‐hydroxy‐[1‐14C]decyl) ‐2,3‐dimethoxy‐5‐methyl‐1,4‐benzoquinone
Authors: Hayashi Nobuyoshi , Kato Shinji 
Published: October 2006

Abstract6‐(10‐Hydroxy‐[1‐14C]decyl)‐2,3‐dimethoxy‐5‐methyl‐1,4‐ benzoquinone (VIII) having a specific activity of 23.4 mCi/mmol was synthesized. 9‐(2‐Hydroxy‐3,4‐dimethoxy‐6‐methyl‐[carbonyl‐14C] benzoyl)nonanol (VI) was obtained from the condensation of 3,4,5‐trimethoxytoluene with 10‐acetoxy‐[1‐14C]decanoyl chloride (V) prepared from K14CN (I). Reduction of VI with hydrogen in the presence of Pd‐Cprovided 10‐(2‐hydroxy‐3,4‐dimethoxy‐6‐methylphenyl)‐[1‐14C]decanol (VII). VII was oxidized with a Fremy's salt to give VIII in 21.5% radiochemical yield. 6‐(10‐Hydroxy‐decyl)‐2‐methoxy‐3‐[14C]methoxy‐5‐methyl‐1,4‐ benzoquinone (XI) was prepared in 34.6% radiochemical yield from the reaction of [14C]dimethyl sulfate with 6‐(10‐hydroxydecyl) ‐3‐hydroxy‐2‐methoxy‐5‐methyl‐1,4‐benzoquinone.
Synthesis of tritium labelled cholecystokinin derivative : [3H]‐Boc‐[Nle28, 31]‐ CCK27–33
Authors: Sasaki N. A. , Funakoshi S. , Potier P. , Morgat J.‐L. , Genet R. , Gacel G. , Charpentier B. , Roques B. P. 
Published: October 2006

AbstractThe synthesis of a new acetylenic analogue of the C‐terminal heptapeptide segment of cholecystokinin (CCK) in which the Met28 and Met31 residues are replaced by two acetylenic precursors of norleucine (Nle), L‐2‐amino‐4‐hexynoic acid (Aha), is described. Reductive tritiation of this acetylenic heptapeptide Boc‐[Aha28, 31]‐CCK27, 33 led to the labelled [3H]‐Boc‐[Nle28, 31]‐CCK27–33 which displays a specific activity of about 150 Ci/mmol. According to its full biological potency, this CCK analogue can be used for various biological assays including binding studies.
A versatile synthesis of C‐5 labeled ornithines
Authors: Wityak John , Palaniswamy Venkatapuram A. , Gould Steven J. 
Published: October 2006

AbstractUsing diethyl (2‐cyanoethyl)acetamidomalonate prepared from either acrylonitrile or 3‐tosylpropionitrile and diethyl acetamidomalonate, reduction with PtO2 and H2 in ethanol followed by acid hydrolysis affords ornithine in 70–95% yield. [5, 5–2H2]Ornithine and [5‐13C, 5‐15N]ornithine were prepared by these procedures.
Tritiated hexadecyl platelet activating factor (PAF)
Authors: Wyrick Steven D. , McClanahan Judy S. , Wykle Robert L. , O'Flaherty Joseph T. 
Published: October 2006

AbstractWe report the synthesis of the natural isomer of [3H]‐lyso platelet activating factor, [3H]‐lyso PAF (1‐0‐[9′,10′‐3H2]‐hexadecyl‐2‐lyso‐sn‐glycero‐3‐phosphocholine) and its conversion by acetylation to [3H]‐PAF(1‐0‐[9′,10′‐3H2]‐hexadecyl‐2‐acetylsn‐glycero‐3‐phosphocholine) for use in in vitro and in vivo metabolic studies. The procedure employed allows the separation of the natural (sn‐1‐0‐alkyl)lyso and unnatural (sn‐3‐0‐alkyl) isomers of the PAF precursors from a racemic mixture. The natural lyso‐Δ9, 10‐1‐0‐hexadecenyl PAF was reduced with 5.0 Ci of carrier free tritium gas to afford the tritiated lyso PAF at a specific activity of 56 Ci/mmole (115 mCi/mg).
Synthesis of 14C‐labeled indeloxazine hydrochloride (YM‐08054), a cerebral activator
Authors: Arima Hideki , Tamazawa Kazuharu 
Published: October 2006

AbstractIndeloxazine hydrochloride, (±)‐2‐[(inden‐7‐yloxy)methyl]morpholine hydrochloride (YM‐08054), a new cerebral activator, was labeled with 14C for metabolic studies. The labeled material with a specific activity of 14.9 mCi/mmol was synthesized in a 42.8% radiochemical yield from potassium [14C]cyanide via a process of ten steps.
Synthesis of 13C‐labelled propylene oxide via 13C‐labelled 2‐chloropropionic acid and 2‐chloropropanol
Authors: Pri‐Bar Ilan , Buchman Ouri 
Published: October 2006

Abstract1‐Methyl‐[2‐13C]ethylene oxide (I) is prepared in a four‐step synthesis, starting from [1‐13C]propionic acid. A method for an efficient α‐chlorination of low carboxylic acids is developed, 2‐chloropropionyl chloride being esterified without separation to give 72% of phenyl‐2‐chloro‐[1‐13C]propionate. The ester is hydrogenated with LiAlH4 to give 95% yield of 2‐chloro‐[1‐13C]propan‐1‐ol which is then subjected to alkaline dehydrochlorination, giving 35% yield of the isolated product (I). This micro‐scale method is also suitable for syntheses of 14C‐labelled epoxides of low molecular weight.
Syntheses of radiolabelled forms of a novel histamine H1 antagonist (SK&F 93944)
Authors: Cashyap M M , Mitchell M B , Osborne D C , Saunders D 
Published: October 2006

AbstractA novel histamine H1 antagonist SK&F 939441, 2‐[4‐(5‐bromo‐3‐methylpyrid‐2‐yl)butylamino]‐5‐(6‐methylpyrid‐3‐yl‐methyl)‐4(3H)‐pyrimidone, has been labelled with carbon‐14 in two different positions for use in metabolism and pharmacoinetic studies. The four stage synthesis of [pyrimidone‐2‐14C] SK&F 93944 (7) from barium [14C]cyanamide is described. The overall radiochemical yield was 38%. [butylamino‐4‐14C] SK&F 93944 (14) was synthesised in four steps from [14C]methyl iodide. The key steps in this synthesis were alkylation of 2‐lithio‐3‐methyl pyridine with [14C]methyl iodide and the bromination of 4‐(3‐methyl‐2‐pyridyl)[4‐14C]butylamine in a liquid sulphur trioxide/freon mixture. The overall radiochemical yield was 1.6% from [14C]methyl iodide.
Synthesis of [2‐14C]dezaguanine mesylate (6‐amino‐1,5‐dihydro‐4H‐imidazo[4,5‐c]pyridin‐4‐one‐6‐14C methanesulfonate), a new antitumor agent
Authors: Hartman Jon D. , Alks Vitauts , Huang C. C. , Cook P. Dan 
Published: October 2006

AbstractDezaguanine mesylate (CI‐908 mesylate, 3‐deazaguanine mesylate, 6‐amino‐1,5‐dihydro‐4H‐imidazo[4,5‐c]pyridin‐4‐one methanesulfonate, 7), a new antitumor agent, was labeled in‐the 2‐position by use of a new synthesis to 3‐deazaguanine. Thus, methyl 4‐(hydroxymethyl)‐1‐(triphenylmethyl‐1H‐imidazole‐5‐carboxylate (10) was converted with thionyl chloride to the corresponding chloromethyl‐derivative 11, which was treated with [14C]‐potassium cyanide to afford the labeled penultimate intermediate, methyl 5‐(cyanomethyl)‐1H‐imidazole‐4‐carboxylate (12). Ring closure of 12 with methanolic ammonia and subsequent salt formation provided [2‐14C]3‐deazaguanine mesylate (13).
Synthesis of 2 deuterium labelled analogs of veralipride
Authors: Staveris S. , Schmitt A. , Jamet G. , Kerr R R. , Ottman L. , Jung L. , Koffel J. C. 
Published: October 2006

AbstractVeralipride was labelled with trideuteromethyl groups first in the o‐methoxy and later in both o‐and m‐methoxy positions respective to the benzamide functions. Hydroxylated benzaldehydes were the starting materials and (CD3)2SO4 the labelling substance. A known synthesis was followed for veralipride‐d3. This synthesis was extensively modified in the final steps for veralipride‐d6 by introducing an ester exchange reaction which increased the overall yield.
Tritium labelled (±)‐10‐[2‐(1‐methyl‐2‐piperidinyl)ethyl]‐2‐(methyl‐mercapto)‐[3‐3H(n)]phenothiazine (thioridazine)
Authors: Wyrick Steven D. , Mailman Richard B. , Niedzwiecki Diane M. 
Published: October 2006

AbstractThe antipsychotic drug, thioridazine, differs from more classical antipsychotic drugs with respect to both some atypical psychopharmacological characteristics and to the critical involvement of active metabolites in its pharmacology. Tritium labelled thioridazine has been prepared in our laboratory by palladium catalyzed reduction of an aryl brominated precursor using carrier free tritium gas in THF. The product is labelled in the 3‐position of the phenothiazine ring system and a specifie activity of 12 Ci/mmole was obtained.
Synthesis of 122I‐ and 125I‐labelled meta‐dimethoxy‐N,N‐dimethyliodophenylisopropylamines
Authors: Mathis Chester A. , Shulgin Alexander T. , Sargent Thornton 
Published: October 2006

AbstractThe syntheses of 122I‐ and 125I‐labelled 2,4‐dimethoxy‐N,N‐dimethyl‐5‐iodophenylisopropylamine, 3,5‐dimethoxy‐N,N‐dimethyl‐2‐iodophenylisopropylamine and 2,6‐dimethoxy‐N,N‐dimethyl‐3‐iodophenylisopropylamine are described. The speed (3 min, including purification) and yield (45‐85%) obtained in direct iodination procedures utilizing chloramine‐T have allowed the use of the short‐lived positron emitter 122I (t1/2 = 3.6 min) in brain blood flow imaging studies. The three appropriate precursors (the meta‐dimethoxy‐N,N‐dimethylphenylisopropylamines) were prepared from the corresponding phenyl acetone analogues by reductive amination employing dimethylamine and NaCNBH3. The ketones were obtained from the appropriate nitrostyrenes through reduction with elemental Fe.
Preparation of methyl 8c, 11c‐octadecadienoate‐17,17,18,18‐d4 and methyl 8c,11c,14c‐octadecatrienoate‐17,17,18,18‐d4
Authors: Adlof R. O. , Emken E. A. 
Published: October 2006

AbstractMulti‐gram quantities of methyl 8c,11c‐octadecadienoate‐17,17,18,18‐d4 and methyl 8c,11c,14c‐octadecatrienoate‐17,17,18,18‐d4 were synthesized for use in human metabolism studies. The deuterium atoms were incorporated using tris(triphenylphosphine)chlororhodium (I) catalyst and deuterium gas. The double bonds in the Δ11 and Δ14 positions were incorporated by acetylenic coupling. The double bond in the Δ8 position was introduced by the Wittig coupling of the mono‐ or di‐unsaturated triphenyl phosphonium halide to 7‐formylheptanoate. The 15‐25% trans isomers formed by the Wittig coupling reaction were removed by silver resin chromatography. Overall yields were 15%, for the diene ester (an 8‐step synthesis) and 12%, for the triene (a 12‐step synthesis). Both compounds were shown to have an isotopic purity of > 97% d4.
Synthesis of 14C‐labelled butoxyethoxyethanol
Authors: Thijssen J. B. A. , Janssen C. G. M. , Verluyten W. L. M. , Heykants J. J. P. 
Published: October 2006

AbstractButoxyethoxyethanol1, an organic solvent used as carrier in the levamisole pour‐on formulation, was synthesized via a Makosza etherification of 1‐14C‐ labelled bromobutane with mono tetrahydropyranyl (T.H.P.) protected diethylene glycol and subsequent removal of the T.H.P. protecting group. The compounds' synthetic yield was 88.8 %; it had a specific activity of 32.5 mci/mmol. The reaction product was radiochemically pure (99.6 %) according to high‐performance liquid chromatography and thin‐layer chromatography in three solvent systems.
Syntheses, resolution optique et radiolyse d' Acides Amines Trities a Haute Activite Specifique. I ‐ D,L‐Lysine (3H‐4,5,6,6); L‐lysine (3H‐4,4,5,5); L‐Leucine (3H‐4,5,5,5); Acide D‐α‐amino Adipique (3H‐4,4,5,5); Acide γ‐Amino Butyrique (3H‐2,2,3,3)
Authors: Ego Dominique , Beaucourt Jean‐Pierre , Pichat Louis 
Published: October 2006

2,6‐Diamino‐4‐hexynoic acid 5 was prepared from 1,4‐dichloro‐2‐butyne and diethyl acetamidomalonate. The catalytic reduction of 5 with tritium led to (4,5,6,6‐3H) DL‐lysine 6′ spec. act. 113 Ci/mM. The catalytic reduction With tritium of L‐2‐amino‐6‐t‐butoxycarbonylamino‐4‐hexynoic acid 7 followed by hydrolysis gave [4,4,5,5‐3H] L‐lysine 6 spec. act. : 120 Ci/mM.DL‐2‐amino‐5,5‐dichloro‐4‐methyl‐4‐pentenoic acid 11 was prepared from 2‐methyl‐1,1,3‐trichloro‐1‐propene and diethyl acetamidomalonate. The optical isomers Were separated by preparative HPLC. The catalytic reduction of the L enantiomer gave [4,5,5,5‐3H] L‐leucine 13 spec. act. 140 Ci/mM.Ethoxycarbonylation of ethyl 2‐acetylamino‐2‐ethoxycarbonyl 4‐pentynoate : 15 in presence of palladium gave triethyl 4‐acetylamino‐1‐butyne‐1,4,4‐tri‐carboxylate 16. Reduction of 16 with tritium followed by hydrolysis gave DL‐[4,4,5,5‐3H]α‐aminoadipia acid 18′ spea. act. 130 Ci/mM. The oxidation of 18′ with L‐aminoxidase led to D‐α‐aminoadipia acid 18 with the same specific activity.Methoxycarbonylation of 3‐phthalimido‐1‐propyne 19 in presence of Pd gave methyl 4‐phthalimido‐2‐butynoate 20 which tritiation followed by hydrolysis led to [2,2,3,3‐3H] GABA 22 spec. act. 109 Ci/mM. 3H NMR analyses Were carried out in each case. Studies on the self radiolysis of these aminoacids during storage are reported.
Synthesis of seven deuteromethyl‐caffeine analogues observation of deuterium isotope effects on cmr analysis
Authors: Falconnet J. B. , Brazier J. L. , Desage M. 
Published: October 2006

AbstractThis article describes synthesis of all 7 N‐trideuteromethyl isotopomers of caffeine by reaction of trideuteromethyl iodide (C2H3I) with the appropriate xanthine molecules.The use of proton. deuterium and carbon‐13‐NMR as a first step in purity assessment revealed 13C‐NMR deuterium isotope effects on the resonance of perdeuteromethyl carbons.
Synthesis of deuterium labelled fluphenazine utilising borane reduction
Authors: Sardessai M. S. , Brander M. J. , Midha K. K. , Hawes E. M. 
Published: October 2006

AbstractTwo new procedures are described for the preparation of di‐ and tetra‐deuterated 10‐[[3‐[4‐(2‐hydroxyethyl)‐1‐piperazinyl]propyl]]‐2‐trifluoromethyl‐10H‐phenothiazine (fluphenazine). Deuterium was introduced in either the 1‐ or the 1‐ and 3‐positions of the propyl side chain by reduction with deuterated borane in tetrahydrofuran of the appropriately substituted N‐10 amide or amido ester. The isotopic purity of the synthesized deuterated products was greater than 99%.
Synthesis of 14C‐ and 2H‐labeled 1,3‐dihydro‐3,3‐dimethyl‐5‐(1,4,5,6‐tetrahydro‐6‐oxo‐3‐pyridazinyl)‐2H‐indol‐2‐one (LY195115), an orally effective positive inotrope
Authors: Robertson David W. , Krushinski Joseph H. , Kau Don 
Published: October 2006

AbstractWe have synthesized 14C‐ and 2H‐labeled 1,3‐dihydro‐3,3‐dimethyl‐5‐(1,4,5,6‐tetrahydro‐6‐oxo‐3‐pyridazinyl)‐2H‐indol‐2‐one (LY195115), an extremely potent, orally‐effective cardiotonic with inotropic and vasodilator activities. The 14C‐label was introduced in the antepenultimate step by reaction of a β‐chloroketone precursor with Na14CN; acid‐catalyzed hydrolysis and cyclization with hydrazine provided the tetrahydropyridazinone bearing the 14C‐label in the oxo‐carbon. 1,3‐Dihydro‐3,3‐di(methyl‐d3)‐2H‐indol‐2‐one was prepared by exhaustive methylation of 1‐acetyl‐1,3‐dihydro‐2H‐indol‐2‐one with sodium hydride and iodomethane‐d3, followed by removal of the nitrogen protecting group. This labeled material was converted in two steps to [2H6]‐LY195115.
N.C.A. [18F]‐labelling of aliphatic compounds in high yields via aminopolyether ‐ supported nucleophilic substitution
Authors: Block Dirk , Klatte Bernd , Knöchel Arndt , Beckmann Rainer , Holm Uwe 
Published: October 2006

AbstractThe nucleophilic introduction of n.c.a. ‐ [18F]‐fluoride into alkanes and carboxylic acids using anion activation by macrocyclic polyethers was investigated.The reactions carried out in the presence of the bicyclic aminopolyether APE 2.2.2. gave rise to high radiochemical yields (40‐65 %) under mild conditions. Important for the successful 18F‐labelling is a suitable cation/polyether couple, which leads to an unsolvated [18F]‐fluoride in a dipolar aprotic solvent and ensures a high ion concentration, thus enhancing the reactivity. Reaction parameters, such as concentration of substrate and APE, the influence of cation, anion and water were studied and optimised.
A simple one‐pot synthesis of cyclopropane [11C]carbonyl chloride. Synthesis and biodistribution of [11C]cyclorphan
Authors: McPherson Daniel W. , Hwang Dah‐Ren , Fowler Joanna S. , Wolf Alfred P. , Macgregor Robert M. , Arnett Carroll D. 
Published: October 2006

AbstractA rapid, one‐pot, synthesis of cyclopropane [11C]carbonyl chloride was developed. This synthesis proceeded in 80% radiochemical yield (EOB) in a synthesis time of 10 minutes. This acid chloride was then used to synthesize a model compound, [11C]cyclorphan, by alkylation of norlevorphanol followed by reduction of the intermediate [11C]amide in an overall synthesis time of 55 minutes and a radiochemical yield of 15% (EOB). The biodistribution of [11C]cyclorphan in control and naloxone pretreated mice showed non‐specific binding and rapid clearance from brain.
Syntbesis of 14C‐labeeed felbamate from phenylacetic‐(methylene‐ 14C) acid
Authors: Choi Yong M. , Kucharczyk Norbert , Sofia R. Duane 
Published: October 2006

AbstractA synthetic procedure for the preparation of 2‐phenyl‐1,3‐propanediol‐2‐14C dicarbamate. starting with phenylacetic‐(methylene‐14C) acid was developed. The procedure from phenylacetic acid to 2‐phenyl‐1,3‐propanediol dicarbamate has four steps via phenylmalonic acid and 2‐phenyl‐1,3‐propanediol. The overall yield of all four steps was 28%.
Synthesis of 4‐(3‐t‐butylamino‐2‐hydroxypropoxy)‐benzimidazol‐2(11c)‐one (cgp 12177)
Authors: Boullais C , Crouzel C , Syrota A 
Published: October 2006

Abstract4‐(3‐t‐butylamino‐2‐hydroxypropoxy)‐benzimidazol‐2 (11C)‐one (CGP 12177) was synthetized in a short time (30 min) and with a specific activity of 130 mCi/μMol for β receptor studies by the positron emission tomography. The radioactive reagent was 11C‐phosgene and the starting material 1‐(3‐t‐butylamino‐2‐hydroxypropoxy)‐2.3‐diamino benzene.
14C‐labeling of a novel fungicide. I. Syntheses of optically active (E)‐and (Z)‐1‐(2,4‐dichlorophenyl)‐4,4‐dimethyl‐2‐(1,2,4‐triazol‐[14C]‐1‐YL)‐1‐penten‐3‐OLS
Authors: Nakatsuka Iwao , Kanamaru Hiroshi , Kamada Takeshi , Kawahara Kazuo , Yoshitake Akira 
Published: October 2006

AbstractA novel fungicide, (‐)(E)‐1‐(2,4‐dichlorophenyl)‐4, 4‐dimethyl‐2(1,2,4‐triazol‐1‐yl)‐1‐penten‐3‐ol (S‐3308 L) and its three optically active stereoisomers were labeled with carbon‐14 at the triazole ring for use in the metabolic and environmental fate studies. 1,2,4‐Triazole‐14C (4) prepared from formamide‐14C (3) was treated with bromopinacolone to give triazolylpinacolone‐14C (5), which was condensed with 2,4‐dichlorobenzaldehyde giving (Z)‐ketone‐14C (6). (Z)‐Ketone‐14C (6) was photoisomerized to (E)‐ketone‐ 14C (7), which was reduced to racemic (Z)‐S‐3308‐ 14C (1) in 20% yield from 3. Reduction of 6 gave racemic (Z))S‐3308‐14C (2) in 23% field from 3. Optical resolution of both racemates 1 and 2 by a HPLC method with a chiral column gave (‐)(E)‐, (+)(E)‐, (‐)(Z)‐ and (+)(Z)‐1‐(2,4‐dichlorophenyl)‐4,4‐dimethyl‐2‐(1,2,4‐triazol‐[14C]‐1‐yl)‐1‐penten‐3‐ols (1a, 1b, 2a and 2b) in essentially Quantitative yields.
Synthesis of 3h‐labelled enalapril maleate
Authors: Bartroli J. , Ramis J. , Marin A. , Forn J. 
Published: October 2006

AbstractThe synthesis of enalapril maleate (MK 421) labelled with tritium at its proline ring is described. Thus, the N′‐hydroxysuccinimidyl ester of a N‐carboxyalkyl alanine derivative was reacted with L‐[4,5‐H] proline and the crude reaction mixture treated with maleic acid to give the maleate salt of enalapril in 27% yield.
A rapid synthesis of [82Br]‐2‐deoxy‐2‐bromo‐D‐mannose and [82Br]‐ 2‐deoxy‐2‐bromo‐D‐glucose using D‐glucal as precursor
Authors: Homma Yoshio , Murase Yuko , Ishii Michiko , Sonehara Kazue 
Published: October 2006

AbstractA new rapid synthesis of [82Br]‐2‐deoxy‐2‐bromo‐D‐mannose and [82Br]‐2‐deoxy‐2‐bromo‐D‐glucose is described. Reaction of 82Br2 with D‐glucal in CHCl3, followed by treatment with 1 N HCl gave [82Br]‐2‐deoxy‐2‐bromo‐D‐mannose and [82Br]‐2‐deoxy‐2‐bromo‐D‐glucose in the yield of 61.1 % and 27.7 %, respectively. The synthesis time was 20 min. The radiochemical purity of [82Br]‐2‐deoxy‐2‐bromo‐D‐mannose and [82Br]‐2‐deoxy‐2‐bromo‐D‐glucose was greater than 95 %. The radiochemical yield of [82Br]‐2‐deoxy‐2‐bromo‐D‐mannose and [82 Br]‐2‐deoxy‐2‐bromo‐D‐glucose was 14.3 % and 31.6 %, respectively. D‐Glucal was shown to be a useful precursor to allow rapid production of usable amounts of glucose analogs such as [75Br]‐2‐deoxy‐2‐bromo‐D‐mannose and [75Br]‐2‐deoxy‐2‐bromo‐D‐glucose.
Ochratoxin A labelled with 14C or 3H in the phenylalanine moiety
Authors: Hult Karl 
Published: October 2006

AbstractOchratoxin A is a mycotoxin produced by Aspergillus and Penicillium moulds. The toxin is an amide formed between phenylalanine and the isocoumarin acid ochratoxin α. Ochratoxin A with high specific radioactivity can be obtained, by substitution of the natural phenylalanine for 14C or 3H‐labelled phenylalanine. Labelled ochratoxin A was formed by condensation of labelled phenylalanine ethylester with an anhydride derivative of ochratoxin α. The intermediate O‐acetyl ochratoxin C was hydrolyzed with pig liver esterase and chymotrypsin to afford ochratoxin A. The overall yield of radioactivity was 50%. Specific activities up to 500 Ci/mol and 100 Ci/mmol for 14C and 3H respectively were obtained.
Methodes de Syntheses de l'idazoxan ‐ RX: 781094 [( Imidazolinyl‐2 ) ‐2‐Benzodioxanne‐1,4]Marque au Tritium a Haute Activite Specifique: Un Ligand Radioactif Antagoniste Selectif des α2‐Adrenorecepteurs Presynaptiques
Authors: Guillaumet G. , Coudert G. , Clement R. , Ponchant P. , Pichat L. 
Published: October 2006

Four methods of syntheses of IDAZOXAN (RX 781094): |2‐(2‐imidazolinyl)‐1,4‐benzodioxane| labelled with tritium: 1 at high specific activity, a selective radioligand presynaptic α2‐ adrenoreceptor antagonist are described. 2‐carbethoxy‐1,4‐benzodioxine 5 was treated with tritium in benzene in presence of Wilkinson's catalyst leading to 2‐carbethoxy [2,3‐3H]‐1,4‐benzodioxane: 6 spec. act. 60 Ci/m which was then condensed in toluene with a reagent made from trimethylaluminium and ethylenediamine giving rise to 1 specific activity 44 Ci/mMole.2‐(carbamido N‐cyanomethyl)1,4‐benzodioxine: 2 was prepared from 2‐chlorocarbonyl‐1,4‐benzodioxine: 10 and 2‐aminoacetonitrile. 2 was reduced with tritium in trifluoroacetic acid in presence of Pd/C giving 8 which, without purification was ring closed into 2 by trimethylaminium treatment. Spec. act. 35.5 Ci/mMole. When reduced with tritium in presence of Wilkinson's catalyst, 7 gave 9 spect. act. 55 Ci/mMole. After purification 9 was again reduced with tritium in trifluoroacetic acid in presence of Pd/C, or PtO2, or Rh/Al2O3 giving 8 which was cyclised into 1 by trimethylaluminium treatment in toluene. spec. act. of 1 was 41.5 ‐ 39 Curies/mMole. 1 was purified by successive preparative thin layer chromatography. The radiochemical purity checked by TLC and PLC was better than 99%. Some observations on the rate of self radiolysis of 1 are reported.