Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents

Abstract

A series of novel arylfluoroquinolones has been prepared. These derivatives are characterized by having a fluorine atom at the 6-position, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position. Structure-activity relationship (SAR) studies indicate that the in vitro antibacterial potency is greatest when the 1-substituent is either p-fluorophenyl or p-hydroxyphenyl and the 7-substituent is either 1-piperazinyl, 4-methyl-1-piperazinyl, or 3-amino-1-pyrrolidinyl. The electronic and spatial properties of the 1-substituent, as well as the steric bulk, play important roles in the antimicrobial potency in this class of antibacterials. As a result of this study, compounds 45 and 41 were found to possess excellent in vitro potency and in vivo efficacy.

Design synthesis and antibacterial activity studies of new thiadiazoloquinolone compounds

“…Much has been learned about how molecular modifications of the core quinolone structure affect the antibacterial profile. The structure-activity relationship of the quinolones has been the subject of extensive reviews [4][5][6][7][8][9][10][11][12][13][14][15][16] . In our continuous effort to develop new chemotherapeutics with enhanced activities against resistant bacterial strains 17,18 , we introduced a new class of tricyclic compounds, namely thiadiazoloquinolones 19 .…”

Regioselective Synthesis of Some Thio Analogues of Quinolone Antibacterials via Borate Complex of Quinolone Carboxylic Acid Catalyzed by DABCO under Microwave Irradiation

“…A five or six membered ring is the most commonly found substitution at position C-7, for example, ciprofloxcine and norfloxacine that are widely used as antibiotics in wide range, have piperazine substitution at C-7 position (Scheme 1). Fluoro quinolones with 7-piperazinyl moiety have been reported to possess potent antibacterial activity [2][3][4][5][6][7][8][9] .…”

New Improved Quinlone Derivatives Against Infection

“…The 3-carboxylic group is considered important for DNA gyrase binding (Chu et al, 1985, Domagala et al, 1988, Sarro & Sarro, 2001. Modifications on this position of quinolone are normally not accepted (Mitscher, 2005).…”