Antituberculosis and antibacterial evaluations of some novel phenyl pyrazolone-substituted 1h-benzo[g]pyrazolo[3,4-b] quinoline-3-ylamine derivatives

Medicinal Chemistry Research

Volumn 21, Issue 12, 2012, Pages 4168-4176

  Parekh, Nikhil M ^a   Maheria, Kalpana C ^a  

^a SARDAR VALLABHBHAI NATIONAL INSTITUTE OF TECHNOLOGY   (India)

Author keywords

1H benzo g pyrazolo 3; 4 b quinoline 3 ylamine; Antibacterial activity; Antituberculosis activity; Synthesis

Indexed keywords

1H BENZO[G]PYRAZOLO[3,4 B]QUINOLINE 3 YLAMINE DERIVATIVE; 3 [4 (1H BENZO[G]PYRAZOLO[3,4 B]QUINOLIN 3 YLAZO) 3 METHYL 5 OXO 4,5 DIHYDRO PYRAZOL 1 YL]BENZENESULPHONIC ACID; 4 (1H BENZO[G]PYRAZOLO[3,4 B]QUINOLIN 3 YLAZO) 2 (2 CHLORO PHENYL) 5 METHYL 2,4 DIHYDRO PYRAZOL 3 ONE; 4 (1H BENZO[G]PYRAZOLO[3,4 B]QUINOLIN 3 YLAZO) 2 (2,5 DICHLORO PHENYL) 5 METHYL 2,4 DIHYDRO PYRAZOL 3 ONE; 4 (1H BENZO[G]PYRAZOLO[3,4 B]QUINOLIN 3 YLAZO) 2 (3 CHLORO PHENYL) 5 METHYL 2,4 DIHYDRO PYRAZOL 3 ONE; 4 (1H BENZO[G]PYRAZOLO[3,4 B]QUINOLIN 3 YLAZO) 2 (3,4 DICHLORO PHENYL) 5 METHYL 2,4 DIHYDRO PYRAZOL 3 ONE; 4 (1H BENZO[G]PYRAZOLO[3,4 B]QUINOLIN 3 YLAZO) 5 METHYL 2 4 TOLYL 2,4 DIHYDRO PYRAZOL 3 ONE; 4 [4 (1H BENZO[G]PYRAZOLO[3,4 B]QUINOLIN 3 YLAZO) 3 METHYL 5 OXO 4,5 DIHYDRO PYRAZOL 1 YL] 2,5 DICHLORO BENZENESULPHONIC ACID; 4 [4 (1H BENZO[G]PYRAZOLO[3,4 B]QUINOLIN 3 YLAZO) 3 METHYL 5 OXO 4,5 DIHYDRO PYRAZOL 1 YL] 3 CHLORO BENZENESULPHONIC ACID; 4 [4 (1H BENZO[G]PYRAZOLO[3,4 B]QUINOLIN 3 YLAZO) 3 METHYL 5 OXO 4,5 DIHYDRO PYRAZOL 1 YL]BENZENESULPHONIC ACID; 6F.4 [4 (1H BENZO[G]PYRAZOLO[3,4 B]QUINOLIN 3 YLAZO) 3 METHYL 5 OXO 4,5 DIHYDRO PYRAZOL 1 YL] 3 METHYL BENZENESULPHONIC ACID; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; BENZENE DERIVATIVE; CIPROFLOXACIN; ETHAMBUTOL; FLUCONAZOLE; ISONIAZID; PYRAZOLONE DERIVATIVE; QUINOLINE DERIVATIVE; RIFAMPICIN; STREPTOMYCIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CONTROLLED STUDY; DIAZOTIZATION; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; ZONE OF INHIBITION;

EID: 84855165269     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9942-4     Document Type: Article

References (22)

1. Abadi AH, Eissa AA, Hassan GS (2003) Synthesis of novel 1,3,4-trisubstituted pyrazole derivatives and their evaluation as antitumor and anti-angiogenic agents. Chem Pharm Bull 51(7): 838-844
2. Craig JC, Person PE (1971) Potential antimalarials. 7. Tribromomethylquinolines and positive halogen compounds. J Med Chem 14(12):1221-1222
3. Dillard RD, Pavey DE, Benslay DN (1973) Synthesis and antiinflammatory activity of some 2,2-dimethyl-1,2-dihydroquinolines. J Med Chem 16(3):251-253
4. Donnell FO, Smyth TJP, Ramachandran VN, Smyth WF (2010) A study of the antimicrobial activity of selected synthetic and naturally occurring quinolines. Int J Antimicrob Agents 35(1): 30-38
5. Eswaran S, Adhikari AV, Shetty NS (2009) Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. Eur J Med Chem 44:4637-4647
6. Isobe M, Nishikawa T, Yamamoto N, Tsukiyama T, Ino A, Okita T (1992) Methodologies for synthesis of heterocyclic compounds. J Heterocycl Chem 29:619-625
7. Jain R, Dixit A, Pandey P (1989) Synthesis of some new 1-carbamoyl-3-aminophenyl-and-1-carbamoyl-3-amino-(2-chlorophenyl)-5-methyl-4 arylpyrazoles as possible potential antidiabetics. J Indian Chem Soc 66:486-489
8. Kerry MA, Boyd GW, Mackay SP, Meth-Cohn O, Platt L (1999) The synthesis of benzo[h]quinolines as topoisomerase inhibitors. J Chem Soc 1:2315-2321
9. Kishor N, Mishra BB, Tripathi V, Tiwari VK (2009) Alkaloids as potential anti-tubercular agents. Fitoterapia 80(3):149-163
10. Makawana JA, Patel MP, Patel RG (2011) Synthesis and in vitro antimicrobial evaluation of pentasubstituted pyridine derivatives bearing the quinoline nucleus. Med Chem Res. doi: 10.1007/s000 44-011-9568-6
11. Meth-Cohn O (1993) The synthesis of pyridines, quinolines and other related systems by the vilsmeier and the reverse vilsmeier method. Heterocycles 35:539-557
12. Mungra DC, Patel MP, Patel RG (2010) Microwave-assisted synthesis of some new tetrazolo [1,5-a]quinoline-based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity. Med Chem Res. doi: 10.1007/s00044-010-9388-0
13. Naik PHR, Naik HSB, Naik TRR, Lamani DS, Aravinda T (2010) An efficient, microwave-assisted, one-pot synthesis of dioxolano quinoline/benzo[h]quinolines as potent antibacterial agents. Phosphorus Sulfur Silicon 185:355-360
14. Parekh N, Maheria K, Patel P (2011a) Studies on microbial activity and dyeing performance of novel acid azo dyes based on 3-(4-aminophenyl)-2-phenylquinazolin-4(3h)-one. J Sci Ind Res 70:525-532
15. Parekh N, Maheria K, Patel P, Rathod M (2011b) Study on antibacterial activity for multidrug resistance stain by using phenyl pyrazolones substituted 3-amino 1H-pyrazolon (3,4-b) quinoline derivative in vitro condition. Int J PharmTech Res 3(1):540-548
16. Patel HV, Vyas KV, Fernandes PS (1990) Synthesis of substituted 6-(30,50-4dimethyl-1H pyrazol-10-yl) quinolines and evaluation of their biological activity. Indian J Chem 29(B):836-842
17. Rani M, Parthiban P, Ramachandran R, Kabilan (2011) Design and synthesis of novel piperazine unit condensed 2,6-diarylpiperidin-4-one derivatives as antituberculosis and antimicrobial agents. Med Chem Res. doi:10.1007/s00044-011-9573-9
18. Rizvi SUF, Siddiqui HL, Ahmad MN, Ahmad M, Bukhari MH (2011) Novel quinolyl-thienyl chalcones and their 2-pyrazoline derivatives with diverse substitution pattern as antileishmanial agents against Leishmania major. Med Chem Res. doi: 10.1007/s00044-011-9647-8
19. Suresh T, Nandha R, Magesh S, Mohan PS (2003) Synthesis, characterization and antimicrobial activities of 4-phenyl-3-thiopyrimido[ 4,5-b]quinolines. Indian J Chem 42(B):2133-2135
20. Thakor SF, Patel DM, Patel MP, Patel RG (2007) Synthesis and antibacterial activity of novel pyrazolo[3,4-b]quinoline based heterocyclic azo compounds and their dyeing performance. Saudi Pharm J 15:1-7
21. Thomas KD, Adhikari AV, Shetty NS (2010) Design, synthesis and antimicrobial activities of some new quinoline derivatives carrying 1,2,3-triazole moiety. Eur J Med Chem 45:3803-3810
22. Tripathi RP, Tewari N, Dwivedi N, Tiwari VK (2005) Fighting tuberculosis: an old disease with new challenges. Med Res Rev 25: 93-131