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Title: Synthesis and antimicrobial evaluation of novel alkylated piperazine-based fluoroquinolone carboxylate derivatives
Authors: Venepally, Vijayendar
Sirisha, K
Kumar, C Ganesh
Reddy Jala, Ram Chandra
Keywords: Piperazine;Fluoroquinolone;Quinolone;Antimicrobial;Antifungal
Issue Date: Apr-2020
Publisher: NISCAIR-CSIR, India
Abstract: In the present study, to synthesize quinolone-piperazine alkylated analogues, initially 3,4-difluoro nitro benzene is reduced to yield 3,4-difluorobenzenamine which is treated with diethyl ethoxymethyl enemalonate to yield diethyl 2-((3,4-difluorophenylamino) methylene) malonate. This has been further cyclized to produce ethyl 6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate which is treated with iodoethane to produce ethyl 1-ethyl-6,7-diifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate. This is hydrolyzed and subsequent nucleophilic substitution with piperazine at 7th position gives quinolone-piperazine derivative. This is alkylated to yield 1-ethyl-6-fluoro-7-(4-alkylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is treated with ethanol to afford the desired ethyl 1-ethyl-6-fluoro-7-(4-hexylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate derivatives. Based on the antimicrobial activity studies, hexyl analog 8a exhibits potent antimicrobial activity against Staphylococcus aureus MTCC 96, Bacillus subtilis MTCC 121, Micrococcus luteus MTCC 2470 (MIC value 1.9µg/mL), with respect to other synthesized compounds and reference drug ciprofloxacin. 8b (heptyl analogue) and 8c (nonyl analogue) show significant activity with MIC value 3.9µg/mL. In the case of antifungal screening, 8a, 8b and 8c show significant antifungal activity against Candida albicans MTCC 3017with MIC value ranged from 3.9 to 7.8µg/mL. Compounds 8a (butyl) shows potent minimum bactericidal concentration activity with MIC value 3.9µg/mL against the tested strains.
Page(s): 474-484
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.59B(04) [April 2020]

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