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Structure–Activity Relationship Investigations Of Leishmanicidal N ‐Benzylcytisine Derivatives
Author(s) -
Turabekova Malakhat A.,
Vinogradova Valentina I.,
Werbovetz Karl A.,
Capers Jeffrey,
Rasulev Bakhtiyor F.,
Levkovich Mikhail G.,
Rakhimov Shukhrat B.,
Abdullaev Nasrulla D.
Publication year - 2011
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/j.1747-0285.2011.01092.x
Subject(s) - quantitative structure–activity relationship , chemistry , halogen , cytotoxicity , amastigote , axenic , stereochemistry , quantum chemical , chemical structure , structure–activity relationship , in vitro , computational chemistry , leishmania , molecule , biochemistry , organic chemistry , biology , parasite hosting , alkyl , world wide web , computer science , bacteria , genetics
In vitro leishmanicidal activity of 16 N ‐benzylcytisine derivatives has been evaluated using Leishmania donovani axenic amastigotes. In general, halogen (bromo‐, chloro‐) derivatives appeared to be more toxic against parasites than their parent compounds. Quantum‐chemical calculations helped to recognize certain patterns in the structure of frontier orbitals related to bioactivity of compounds. Thus, the presence of halogen atom is shown to have a significant effect on both distribution and the energy of LUMOs thereby on potent activity that was also confirmed by Quantitative‐Structure Activity Relationship (QSAR) analysis. Experimentally and theoretically observed structure–cytotoxicity relationships are described.