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Synthetic piperine amide analogs with antimycobacterial activity
Author(s) -
Philipova Irena,
Valcheva Violeta,
Mihaylova Rositsa,
Mateeva Mina,
Doytchinova Irini,
Stavrakov Georgi
Publication year - 2018
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.13140
Subject(s) - antimycobacterial , amide , piperine , moiety , chemistry , stereochemistry , cytotoxicity , piperidine , selectivity , biological activity , monoterpene , mycobacterium tuberculosis , combinatorial chemistry , organic chemistry , biochemistry , in vitro , tuberculosis , medicine , pathology , catalysis
Piperine amide analogs are synthesized by replacement of the piperidine moiety with different types of cyclic amines, including adamantyl and monoterpene‐derived fragments. The compounds are screened for activity against Mycobacterium tuberculosis H37Rv. The most potent compounds are the 1‐adamantyl and the monoterpene‐derived hybrids, which combine nanomolar antimycobacterial activity with low cytotoxicity against human cells. The presence of quaternary carbon atom as main structural requirement for anti‐ TB activity is pointed out by a QSAR study. The most promising compound is the (+)‐isopinocampheylamine‐derived amide which is characterized with selectivity index of 1387.8.