Synthesis of two optically active calcium channel antagonists labelled with carbon-11 for in vivo cardiac PET imaging

Dolle, Frédéric; Hinnen, Françoise; Valette, Héric; Fuseau, Chantal; Duval, Raphaël; Peglion, Jean‐Louis; Crouzel, C.

doi:10.1016/s0968-0896(97)00024-2

Cited by 29 publications

(11 citation statements)

References 17 publications

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“…The formation of compounds 8 and 9 can be rationalized asexplained by an in situ intramolecular oxidation-reduction reaction of compound 2 (Scheme 4), since because it is well known that the dihydropyridine moiety comport oneselfbehaves as a reductive system [10,11,12] and the nitrophenyl framework could acts as an oxiddizingant agent [13]. We presume that one of the first steps could be the formation of the N-OH intermediates you 15 and subsequent cyclization gives compound 8 .…”

Section: Results Aand Discussionmentioning

confidence: 99%

Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

et al. 2001

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The reaction of 5-hydroxy-2-nitrobenzaldehyde with ethyl acetoacetate in ammonia gave the two expected isomeric 1,4- and 1,2-dihydropyridines resulting from the normal Hantzsch reaction. However, the combination of 2-nitrobenzaldehyde with ethyl acetoacetate under the same conditions yielded four products: the two normal isomeric dihydropyridines and two tricyclic compounds. When we attempted to independently synthesize the two tricyclic compounds by reductive cyclization of 4-(2-nitrophenyl)-2,6-dimethyl-3,5-dicarbetoxy-1,4-dihydropyridine and 2-(2-nitrophenyl)-4,6-dimethyl-3,5-dicarbetoxy-1,2-dihydropyridine with tin (II) chloride in hydrochloric acid media, we obtained instead an indole and a quinoline derivative, respectively.

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Section: Results Aand Discussionmentioning

confidence: 99%

Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

et al. 2001

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“…The dextroisomer (D-isomer) (S-12967) was 6-to 18-fold less potent than the levoisomer (L-isomer) (S-12968). 24 Nomoto et al 25 synthesized pyridazinone derivatives of KF15232. These compounds were separated into both diastereoisomers, and each was converted to an optically pure form (.99%) enantioselectively.…”

Section: Preparation Synthesis and Characterizationmentioning

confidence: 99%

Chiral Cardiovascular Drugs

Ranade¹,

Somberg

2005

American Journal of Therapeutics

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Stereochemistry in drug molecules is rapidly becoming an important aspect in drug research, design, and development. Recently, individual stereoisomers of drug molecules with asymmetric centers such as fexofenadine, cetirizine, verapamil, fluoxetine, levalbutarol, and amphetamine, for example, have been separated and developed as individual drugs. These stereoisomers have different therapeutic activity, and each isomer has contributed differently with respect to its formulation's pharmacologic activity, side effects, and toxicity. The present overview discusses chirality among a select group of cardiovascular drugs, their stereochemical synthesis/preparation, isolation techniques using chiral chromatography, methods for confirmation of their enantiomeric purity, pharmacodynamics, and pharmacokinetics. Chirality has been visualized as an important factor in cardiovascular research. It is also becoming evident in other areas of therapeutics.

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“…Since that time, several dihydropyridines have been separated on the semipreparative scale for the study of their inversion by oxidation and electroreduction; 7 fluorenone DHP derivatives were separated on Chiralpak AD 8 giving sizeable amounts of the individual enantiomers; two couples of optically active labelling precursors of SN11568 have been preparatively resolved on home-made Chiralcel OF whereas the analytical check of the enantiomeric purity was performed on a Chiralpak AD column. 9 Semipreparative chromatographic purification of the enantiomers of amlodipine was obtained on a semipreparative Chiral-AGP column. 10 These selected examples deal with actual semipreparative resolutions, however one may take advantage of the numerous examples of analytical separations of DHP in literature, provided they are available in a molecularly oriented factual database format.…”

Section: Resultsmentioning

confidence: 99%

Resolution of some 4-benzofurazanyl and 4-benzofuroxanyl 1,4-dihydropyridine derivatives by chiral HPLC on Whelk-o1 and some polysaccharide chiral stationary phases

et al. 1999

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The chromatographic chiral resolution of racemic methyl 1,4‐dihydro‐2,6‐dimethyl‐5‐nitro‐4‐benzofurazanyl‐3‐carboxylates 1 and 2 and their benzofuroxanyl analogues 3 and 4 were studied on Whelk‐O1, Chiralcel OD‐H, Chiralcel OJ, and Chiralpak AD and AS. These CSPs were selected on the basis of the results of structural searches in Chirbase. Examination of the data and cluster analysis pointed out the influence of benzofurazane–benzofuroxane change versus α–β connection change on retention and enantioselectivity, respectively. The major contribution to the retention change arose from the type of heterocycle, whereas the major contribution to the enantioselectivity change came from the mode of connection (α or β) almost irrespective of the nature of the heterocycle. It resulted in a similarity of behaviour between 1 and 2 on one hand and 3 and 4 on the other as far as capacity factors were concerned, and in a similarity of behaviour between 1 and 3 on the one hand and 2 and 4 on the other as far as enantioselectivities were concerned. Chiralpak AS was selected for semipreparative resolution of the enantiomers. The study of several CSPs allowed us to obtain correlations of structure with retention and enantioselectivity as well as the choice of a semipreparative support to provide the quantities for biological tests. Chirality 11:602–608, 1999. © 1999 Wiley‐Liss, Inc.

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Synthesis of two optically active calcium channel antagonists labelled with carbon-11 for in vivo cardiac PET imaging

Cited by 29 publications

References 17 publications

Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

Chiral Cardiovascular Drugs

Resolution of some 4-benzofurazanyl and 4-benzofuroxanyl 1,4-dihydropyridine derivatives by chiral HPLC on Whelk-o1 and some polysaccharide chiral stationary phases

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