Design, synthesis and docking studies of some novel (R)-2-(4′- chlorophenyl)-3-(4′-nitrophenyl)-1,2,3,5-tetrahydrobenzo[4,5] imidazo [1,2-c]pyrimidin-4-ol derivatives as antitubercular agents

European Journal of Medicinal Chemistry

Volumn 83, Issue , 2014, Pages 245-255

  Barot, Kuldipsinh P ^a   Jain, Shailesh V ^a   Gupta, Nirzari ^a   Kremer, Laurent ^b,c   Singh, Shubhra ^b,e,f   Takale, Vijay B ^d   Joshi, Kruti ^d   Ghate, Manjunath D ^a  

^a NIRMA UNIVERSITY   (India)

^b CNRS   (France)

^c INSERM   (France)

^d Piramal Enterprises Limited   (India)

^e IFTM UNIVERSITY   (India)

^f CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Benzimidazole derivatives; Cytotoxicity assay; Docking study; In vitro antitubercular activity; Structure activity relationship (SAR); Tuberculosis

Indexed keywords

2 (2' 6' DICHLOROPHENYL) 3 (3' HYDROXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (2' 6' DIMETHYLPHENYL) 3 (2' METHOXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (2' 6' DIMETHYLPHENYL) 3 (3' HYDROXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (2' 6' DIMETHYLPHENYL) 3 (4' HYDROXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (2' 6'' DIMETHYPHENYL) 3 (2' AMINO 3,4 DIMETHYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (2' METHOXYPHENYL) 3 (2' HYDROXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (3' 5' DICHLOROPHENYL) 3 (2' CHLOROPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (3' 5' DICHLOROPHENYL) 3 (2' METHOXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (3' 5' DICHLOROPHENYL) 3 (3'4' DIMETHOXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (3' 5' DICHLOROPHENYL) 3 (4' CHLOROPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (4 NITROSTYRYL) 1H BENZO[D]IMIDAZOLE; 2 (4' BROMOPHENYL) 3 (4' HYDROXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (4' CARBOXYPHENYL) 3 (2' HYDROXY 5 METHOXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (4' CHLOROPHENYL) 3 (4' NITROPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (4' METHOXYPHENYL) 3 (3' BROMOPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (4' METHOXYPHENYL) 3 (3' PYRIDINYLPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (4' METHOXYPHENYL) 3 (4' METHOXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (4' NITROPHENYL) 3 (2' NITROPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (4' NITROPHENYL) 3 (3' NITROPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 4 CHLORO N [[2 (4 NITROSTYRYL) 1H BENZO IMIDAZOL 1 YL]METHYL]ANILINE; 4 CHLORO N [[2 [(2,3) 3 (4 NITROPHENYL)OXIRAN 2 YL] 1H BENZO[D]IMIDAZOL 1 YL]METHYL]ANILINE; ARGININE; BENZIMIDAZOLE DERIVATIVE; FTSZ PROTEIN; GLYCINE; PHENYLENEDIAMINE; PYRIMIDINE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; 2 (2',6 DIMETHYLPHENYL) 3 (3' HYDROXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (2',6' DICHOLROPHENYL) 3 (3' HYDROXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (2',6' DIMETHYLPHENYL) 3 (2' AMINO,3,4 DIMETHYLPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (2',6' DIMETHYLPHENYL) 3 (2' METHOXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (2',6' DIMETHYLPHENYL) 3 (4' HYDROXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (3',5' DICHLOROPHENYL) 3 (2' CHLOROPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (3',5' DICHLOROPHENYL) 3 (2' METHOXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (3',5' DICHLOROPHENYL) 3 (3',4' DIMETHOXYPHENYL) 1,2,3,5 TETRAHYDROBEZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (3',5' DICHLOROPHENYL) 3 (4' CHLOROPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (4' CARBOXYLPHENYL) 3 (2' HYDROXY,5 METHOXYPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL; 2 (4' CHLOROPHENYL) 3 (4' NITROPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZO[1,2 C]PYRIMIDIN 4 OL DERIVATIVE; 2 (4' NITROPHENYL) 3 (3' NITROPHENYL) 1,2,3,5 TETRAHYDROBENZO[4,5]IMIDAZOL[1,2 C]PYRIMIDIN 4 OL; 2 METHYL 1H BENZO[D]IMIDAZOLE; 4 CHLORO N[[2 (4 NITROSTYRYL) 1H BENZO[D]IMIDAZOL 1 YL]METHYL]ANILINE; 4 CHLORO N[[2 [3 (4 NITROPHENYL)OXIRAN 2 YL] 1H BENZO[D]IMIDAZOL 1 YL]METHYL]ANILINE; ISONIAZID; PHENYLENEDIAMINE DERIVATIVE; 2-(4'-CHLOROPHENYL)-3-(4'-NITROPHENYL)-1,2,3,5-TETRAHYDROBENZO(4,5)IMIDAZO(1,2-C)PYRIMIDIN-4-OL; BACTERIAL PROTEIN; CYTOSKELETON PROTEIN; FTSZ PROTEIN, BACTERIA; IMIDAZOLE DERIVATIVE; PYRIDINE DERIVATIVE;

ANTITUBERCULAR ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL INTERACTION; COMPUTER MODEL; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; IN VITRO STUDY; INFRARED SPECTROMETRY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR DOCKING; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; VERO CELL LINE; X RAY ANALYSIS; ANIMAL CELL; CHEMICAL ANALYSIS; CONTROLLED STUDY; CRYSTALLOGRAPHY; DRUG PURITY; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR INTERACTION; TEMPERATURE SENSITIVE MUTANT; ANIMAL; CHEMISTRY; CHLOROCEBUS AETHIOPS; DRUG EFFECTS; METABOLISM; PROTEIN CONFORMATION; SYNTHESIS;

ANIMALS; ANTITUBERCULAR AGENTS; BACTERIAL PROTEINS; CERCOPITHECUS AETHIOPS; CHEMISTRY TECHNIQUES, SYNTHETIC; CYTOSKELETAL PROTEINS; DRUG DESIGN; IMIDAZOLES; MOLECULAR DOCKING SIMULATION; MYCOBACTERIUM TUBERCULOSIS; PROTEIN CONFORMATION; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS;

EID: 84903164958     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.06.019     Document Type: Article

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