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Synthesis and Biological Activity of Usnic Acid Enamine Derivatives Full article

Journal Chemistry of Natural Compounds
ISSN: 0009-3130 , E-ISSN: 1573-8388
Output data Year: 2015, Volume: 51, Number: 4, Pages: 646-651 Pages count : DOI: 10.1007/s10600-015-1376-7
Tags usnic acid; diamines; quaternized derivatives; cytotoxicity; antimycobacterial activity; antibacterial activity
Authors Luzina O. A. 1 , Sokolov D. N. 1 , Pokrovskii M. A. 2 , Pokrovskii A. G. 2 , Bekker O. B. 3 , Danilenko V. N. 3 , Salakhutdinov N. F. 1,2
Affiliations
1 (Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3 (Данные Web of science) NI Vavilov Inst Gen Genet, Moscow 119991, Russia

Abstract: Enamine-derivatives of both enantiomers of usnic acid and the corresponding compounds with a quaternized N atom were synthesized. Compounds 3 and 4 exhibited moderate cytotoxic activity. All quaternized compounds were inactive against the tested tumor cell lines. Quaternized compounds 7 and 8 showed high antimycobacterial activity against Mycobacterium smegmatis, the primary test species for screening antituberculosis drugs. It was shown that the activity dropped in correlation with an increase of the length of the linker between the N atoms. Compound (+)- 8 inhibited effectively the growth of pathogenic Grampositive microorganisms Staphylococcus aureus, S. epidermidis, Streptococcus pneumoniae, and Enterococcus faecalis.
Cite: Luzina O.A. , Sokolov D.N. , Pokrovskii M.A. , Pokrovskii A.G. , Bekker O.B. , Danilenko V.N. , Salakhutdinov N.F.
Synthesis and Biological Activity of Usnic Acid Enamine Derivatives
Chemistry of Natural Compounds. 2015. V.51. N4. P.646-651. DOI: 10.1007/s10600-015-1376-7 WOS Scopus РИНЦ
Dates:
Published print: Jul 1, 2015
Published online: Jul 23, 2015
Identifiers:
Web of science WOS:000359431500010
Scopus 2-s2.0-84938989741
Elibrary 24005225
OpenAlex W969405451
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