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Synthesis, Structure, and Antibacterial Activity of 4‐Imino‐1, 4‐dihydrocinnoline‐3‐carboxylic Acid and 4‐Oxo‐1, 4‐dihydrocinnoline‐3‐carboxylic Acid Derivatives as Isosteric Analogues of Quinolones
Author(s) -
Stańczak Andrzej,
Ochocki Zbigniew,
Martynowski Dariusz,
Główka Marek,
Nawrot Ewa
Publication year - 2003
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.200390000
Subject(s) - chemistry , antibacterial activity , carboxylic acid , substituent , nalidixic acid , chemical synthesis , stereochemistry , antibacterial agent , imine , biological activity , bacteria , organic chemistry , in vitro , antibiotics , ciprofloxacin , biochemistry , genetics , catalysis , biology
Abstract Chemical modification of cinnoxacin was studied with the aim of improving its antibacterial activity and spectrum. A series of 4‐imino‐1, 4‐dihydrocinnoline‐3‐carboxylic acid derivatives was synthesized and their in vitro antibacterial activity was evaluated. These derivatives were designed as isosteric analogues of fluoroquinolones and are characterized by the presence of an imine group instead of an oxo group at the 4‐position and a nitrogen atom in position 2. The crystal structure of one analogue determined by X‐ray diffraction shows the dipolar formof the compound in the solid state. The in vitro antibacterial activity of the synthesized compounds against Gram‐positive and Gram‐negative bacteria was examined. The MIC of the most active compounds lies in the range of the first generation of quinolones such as nalidixic acid. The compounds with dichlorobenzyl substituent show enhanced activity against Gram‐positive bacteria.