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Synthesis and In‐Vitro Antimycobacterial Activity of Fluoroquinolone Derivatives Containing a Coumarin Moiety
Author(s) -
Guo Qiang,
Liu MingLiang,
Feng LianShun,
Lv Kai,
Guan Yan,
Guo HuiYuan,
Xiao ChunLing
Publication year - 2011
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201000256
Subject(s) - antimycobacterial , gatifloxacin , lipophilicity , ciprofloxacin , chemistry , coumarin , mycobacterium smegmatis , moiety , in vitro , stereochemistry , moxifloxacin , combinatorial chemistry , mycobacterium tuberculosis , organic chemistry , biochemistry , antibiotics , medicine , tuberculosis , pathology
A series of gatifloxacin, ciprofloxacin, and 8‐OCH 3 ciprofloxacin coumarin derivatives with remarkable improvement in lipophilicity as compared to the parent fluoroquinolones was designed, synthesized, and characterized by 1 H‐NMR, MS, and HRMS. These derivatives were evaluated for their in‐vitro activity against Mycobacterium smegmatis CMCC 93202 and MTB H37Rv ATCC 27294. All of the synthesized compounds were less active than the parent compounds against M. smegmatis CMCC 93202, but the activity of compound 6 was found to be 2–8‐fold more potent than ciprofloxacin, 8‐OCH 3 ciprofloxacin, moxifloxacin, and rifampin, and comparable to gatifloxacin against MTB H37Rv ATCC 27294. These results indicated that the lipophilicity of the tested compounds is not the sole parameter affecting antimycobacterial activity.