Natural product inspired diversity oriented synthesis of tetrahydroquinoline scaffolds as antitubercular agent.
An efficient natural product inspired diversity oriented syn thesis of tetrahydroquinoline analogues has been developed using the natural carbohydrate derived solid acid catalyst via multicomponent aza-Diels-Alder reaction of imine (generated in situ from aromatic amine and aldehyde) with dienophile in acetonitrile in a diastereoselective manner. The use of water as solvent reverses the diastereoselectivity toward the cis isomer. Interestingly, tricyclic pyrano/furano benzopyran with cis diastereoselectivity is obtained when salicylaldehyde is used as an alternative of aromatic aldehyde under the same condition. These synthesized quinolines and benzopyrans analogues have been evaluated for their Antitubercular activity against M. tuberculosis H₃₇Ra, and M. tuberculosis H₃₇Rv, and some of the analogues shows better activity profile than their natural product analogues. The protocol is not only mild, efficient, ecofriendly, but also involves reusable and biodegradable catalyst and provides route for both the diastereoisomer.
Central Drug Research Institute, CSIR, Lucknow, India. dratulsax@gmail.com
Atul
A
Kumar
Suman
S
Srivastava
Garima
G
Gupta
Vinita
V
Chaturvedi
Sudhir
S
Sinha
R
R
Srivastava
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001688:Biological Products / Q000737:chemistry* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology
D000995:Antitubercular Agents; D001688:Biological Products; D011804:Quinolines; C542964:1,2,3,4-tetrahydroquinoline