Synthesis and evaluation of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4- (2-(4-substitutedpiperazin-1-yl)acetyl)piperazin-1-yl)quinoline-3-carboxylic acid derivatives as anti-tubercular and antibacterial agents

European Journal of Medicinal Chemistry

Volumn 71, Issue , 2014, Pages 324-332

  Suresh, Narva ^a   Nagesh, Hunsur Nagendra ^a   Renuka, Janupally ^a   Rajput, Vikrant ^b   Sharma, Rashmi ^b   Khan, Inshad Ali ^b   Kondapalli Venkata Gowri, Chandra Sekhar ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

^b CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

Author keywords

Anti tubercular activity; Antibacterial activity; Cytotoxicity; Fluoroquinolone; Supercoiling assay

Indexed keywords

1 CYCLOPROPYL 6 FL UORO 7 [4 (2 {4 METHYLPIPERAZIN 1 YL} ACETYL)PIPERAZIN 1 YL] 4 OXO 1,4 DIHYDROQUINOLONE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 (2 {4 (1 PHENYLETHYL) PIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 (2 {4 (3 TRIFLUOROMETHYL)PHENYL)PIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 (2 {4 (PYRIDINE 2 YL) PIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 (2 {4 (PYRIMIDINE 2 YL)PIPERAZIN 1 YL)PIPERAZIN 1 YL] 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 (2 {4 M TOLYLPIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 (2 {4 PHENYLPIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7 [4 (2 {4 (3 HYDROXYPHENYL)PIPERAZIN 1 YL}ACETYLPIPERAZIN 1 YL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7 [4 (2 {4 (3 METHOXYPHENYL)PIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7 [4 (2 {4 (4 NITROPHENYL)PIPERAZIN 1 YL}PIPRAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 7 [4 (2 {4 (2 (DIMETHYLAMINO)ETHYL) PIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 7 [4 (2 {4 (3,4 DIFLUOROPHENYL)PIPERAZIN 1 YL}PIPERAZIN 1 YL] 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 7 [4 (2 {4 (3,4 DIMETHOXYPHENYL)PIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 7 [4 (2 {4 ETHYLPIPERAZIN 1 YL}ACETYL) PIPERAZIN 1 YL] 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 (2 {4 (2 CHLOROPHENYL)PIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1 CYCLOPROPYL FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 (2 {4 (2 CYANOPHENYL)PIPERAZIN 1 YL}ACETYL) PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 (2 {4 (4 CHLOROPHENYL)PIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 (2 {4 (4 CYANOPHENYL)PIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 (2 {4 (BIS(4 FLUOROOPHENYL)METHYL)PIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1 CYCLO PROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 (2 {4 ACETYLPIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLC ACID; 7 [4 (2 {4 BENZHYDRYLPIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 (2 {4 BENZYLPIPERAZIN 1 YL}ACETYL)PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; ANTIINFECTIVE AGENT; CARBOXYLIC ACID DERIVATIVE; CIPROFLOXACIN; ENOXACIN; LOMEFLOXACIN; NORFLOXACIN; OFLOXACIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; 1 CYCLOPROPYL 6 FLUORO 1,4 DIHYDRO 4 OXO 7 [4 [2 (4 SUBSTITUTEDPIPERAZIN 1 YL)ACETYL]PIPERAZIN 1 YL]QUINOLINE 3 CARBOXYLIC ACID DERIVATIVE; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 [2 (4 M TOLYLPIPERAZIN 1 YL)ACETYL]PIPERAZIN 1 YL] 1,4 DIHYROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 [2 (4 PHENYLPIPERAZIN 1 YL)ACETYL]PIPERAZIN 1 YL] 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 [2 [4 (1 PHENYLETHYL)PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL] 1,4 DIHYROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 [2 [4 (3 FLUOROMETHYL)PHENYL]PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL] 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 [2 [4 (PYRIDINE 2 YL)PIPERAZIN 1 YL]ACETYL)PIPERAZIN 1 YL] 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 [4 [2 [4 (PYRIMIDINE 2 YL)PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 L] 1,4 DIHYSROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7 [4 [2 (4 METHYLPIPERAZIN 1 YL)ACETYL]PIPERAZIN 1 YL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7 [4 [2 [4 (3 HYDROXYPHENYL)PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7 [4 [2 [4 (3 METHOXYPHENYL)PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CABOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7 [4 [2 [4 (4 NITROPHENYL)PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL]ACETYL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CABOXYLIC ACID; 1 CYCLOPROPYL 7 [4 [2 (4 ETHYLPIPERAZIN 1 YL)ACETYL]PIPERAZIN 1 YL] 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 7 [4 [2 [4 (3,4 DIFLUOROPHENYL)PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL] 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 7 [4 [2 [4 (3,4 DIMETHOXYPHENYL)PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL]PIPERAZIN 1 YL] 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE CARBOXYLIC ACID; 1 CYCLOPROPYL 7 [4 [2 [4 [2 (DIMETHYLAMINO)ETHYL]PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL] 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 (2 (4 BENZHYDRYLPIPERAZIN 1 YL)ACETYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [2 [4 (2 CHLOROPHENYL)PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXOX 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [2 [4 (2 CYANOPHENYL)PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL]1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [2 [4 (4 ACTYLPIPERAZIN 1 YL)ACETYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [2 [4 (4 BENZYLPIPERAZIN 1 YL)ACETYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [2 [4 (4 CHLOROPHENYL)PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [2 [4 (4 CYANOPHENYL)PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [2 [4 [BIS(4 FLUOROOPHENYL)METHYL]PIPERAZIN 1 YL]ACETYL]PIPERAZIN 1 YL] 1 CYCLO PROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; ANTIBIOTIC AGENT;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTITUBERCULAR ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS AUREUS; ANALYTIC METHOD; ANIMAL EXPERIMENT; ANIMAL MODEL; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MINIMUM BACTERICIDAL CONCENTRATION; STRUCTURE ACTIVITY RELATION;

ANTI-TUBERCULAR ACTIVITY; ANTIBACTERIAL ACTIVITY; CYTOTOXICITY; FLUOROQUINOLONE; SUPERCOILING ASSAY;

ANTI-BACTERIAL AGENTS; CARBOXYLIC ACIDS; ESCHERICHIA COLI; ESCHERICHIA COLI INFECTIONS; HALOGENATION; HUMANS; MYCOBACTERIUM TUBERCULOSIS; QUINOLINES; STAPHYLOCOCCAL INFECTIONS; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP; TUBERCULOSIS;

EID: 84889603040     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.10.055     Document Type: Article

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