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Conformationally Constrained Analogs of N ‐Substituted Piperazinylquinolones: Synthesis and Antibacterial Activity of N ‐(2,3‐Dihydro‐4‐hydroxyimino‐4 H ‐1‐benzopyran‐3‐yl)‐piperazinylquinolones
Author(s) -
Emami Saeed,
Foroumadi Alireza,
Samadi Nasrin,
Faramarzi Mohammad A.,
Rajabalian Saeed
Publication year - 2009
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.200800182
Subject(s) - enoxacin , norfloxacin , chemistry , piperazine , stereochemistry , moiety , benzopyran , substituent , antibacterial activity , bicyclic molecule , benzothiazole , antibacterial agent , quinolone , ciprofloxacin , quinazolinone , levofloxacin , combinatorial chemistry , bacteria , antibiotics , organic chemistry , biochemistry , biology , genetics
A series of novel quinolone agents bearing a particular bulky and conformationally constrained bicyclic substituent (2,3‐dihydro‐4‐hydroxyimino‐4 H ‐1‐benzopyran‐3‐yl‐ moiety) on the piperazine ring of 7‐piperazinyl quinolones (norfloxacin, enoxacin, ciprofloxacin, and levofloxacin) were synthesized and evaluated against a panel of Gram‐positive and Gram‐negative bacteria. Among these derivatives, ciprofloxacin counterpart 9c , highly inhibited the tested Gram‐positive bacteria, superior to that of the reference drugs, and displayed antibacterial activity at non‐cytotoxic concentrations.