Synthesis of chiral 4-pyrazolyl dihydropyridines and their enantiomeric separation

Synthesis of chiral 4-pyrazolyl dihydropyridines and their enantiomeric separation

Kumar, Rakesh; Yadav, Neha; Arora, Jyoti; Prasad, Ashok K

Abstract:

The 1,4-dihydropyridines are the most effective of the calcium antagonists or calcium channel blockers. This class also includes compounds that have exactly the opposite action profile and are known as calcium agonists. There are even instances in which this reversal of activity is found between enantiomers. We herein report the efficient chiral synthesis of DHP derivatives. In contrast to the techniques used previously in our enantioselective Hantzsch variant the chirality information is introduced using two different β-keto esters. The separation of respective enantiomers of 1a is achieved using enzymatic method and calcium channel antagonist activity of the synthesised pure enantiomers is under progress.

The 1,4-dihydropyridines are the most effective of the calcium antagonists or calcium channel blockers. This class also includes compounds that have exactly the opposite action profile and are known as calcium agonists. There are even instances in which this reversal of activity is found between enantiomers. We herein report the efficient chiral synthesis of DHP derivatives. In contrast to the techniques used previously in our enantioselective Hantzsch variant the chirality information is introduced using two different β-keto esters. The separation of respective enantiomers of 1a is achieved using enzymatic method and calcium channel antagonist activity of the synthesised pure enantiomers is under progress.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013101521523

Referências bibliográficas

• [1] 1 Hadjebia, M.; Hashtroudib, M.; Bijanzadeh, H.R.; Balalaie, S. Helvetica Chimica Acta 2011, 94, 382-388.
• [2] 2 Rudong, S.; Velazquez, C.; Knaus, E.E. J. Med. Chem. 2004, 47, 254-261.
• [3] 3 Enders, D.; Miller, S.; Demir, A. S. Tetrahedron Letters 1988, 29, 6437-6440.

Como citar:

Kumar, Rakesh; Yadav, Neha; Arora, Jyoti; Prasad, Ashok K; "Synthesis of chiral 4-pyrazolyl dihydropyridines and their enantiomeric separation", p-133-133. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013101521523