Synthesis of new 4-(2,5-dimethylpyrrol-1-yl)/4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: A novel class of potential antibacterial, antifungal and antitubercular agents

Medicinal Chemistry Research

Volumn 22, Issue 3, 2013, Pages 1073-1089

  Joshi, S D ^a   More, Yogesh ^a   Vagdevi, H M ^b   Vaidya, V P ^c   Gadaginamath, G S ^a   Kulkarni, V H ^a  

^a S E T S COLLEGE OF PHARMACY   (India)

^b Department of Chemistry   (India)

^c KUVEMPU UNIVERSITY   (India)

Author keywords

Acid hydrazide derivatives; Antibacterial activity; Antifungal activity; Antitubercular activity; Broth dilution assay method; Cytotoxicity; Pyrroles

Indexed keywords

2 (2 NITROPHENYL) 5 [4 (1H PYRROL 1 YL)PHENYL] 1,3,4 OXADIAZOLE; 2 (4 BROMOPHENYL) 5 [4 (1H PYRROL 1 YL)PHENYL] 1,3,4 OXADIAZOLE; 2 (4 CHLOROPHENYL) 5 [4 (1H PYRROL 1 YL)PHENYL] 1,3,4 OXADIAZOLE; 2 (4 NITROPHENYL) 5 [4 (1H PYRROL 1 YL)PHENYL] 1,3,4 OXADIAZOLE; 2 [4 FLUORO 3 (TRIFLUOROMETHYL)PHENYL] 5 [4 (1H PYRROL 1 YL)PHENYL] 1,3,4 OXADIAZOLE; 3 ACETYL 5 [4 (2,5 DIMETHYLPYRROL 1 YL)PHENYL] 2 (2 CHLOROPHENYL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 [4 (2,5 DIMETHYLPYRROL 1 YL)PHENYL] 2 PHENYL 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 4 (2,5 DIMETHYLPYRROL 1 YL)BENZOIC ACID; 4 (2,5 DIMETHYLPYRROL 1 YL)BENZOIC ACID[1 (4 AMINOPHENYL)ETHYLIDENE]HYDRAZIDE; 4 AMINO 5 [4 (2,5 DIMETHYLPYRROL 1 YL)PHENYL] 2,4 DIHYDRO 1,2,4 TRIAZOLE 3 THIONE; 5 [4 (2,5 DIMETHYLPYRROL 1 YL)PHENYL] 1,3,4 OXIDIAZOLE 2 THIOL; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; CIPROFLOXACIN; FLUCONAZOLE; HYDRAZIDE DERIVATIVE; N (4 PYRROL 1 YL) 2 BROMO BENZOYL)BENZOIC ACID HYDRAZIDE; N (4 PYRROL 1 YL) 2 NITRO BENZOYL)BENZOIC ACID HYDRAZIDE; N (4 PYRROL 1 YL) 3 NITRO BENZOYL)BENZOIC ACID HYDRAZIDE; N (4 PYRROL 1 YL) 4 BROMO BENZOYL)BENZOIC ACID HYDRAZIDE; N ACETYL 4 (2,5 DIMETHYLPYRROL 1 YL)BENZOIC ACID HYDRAZIDE; N' (1 BENZYLIDENE) 4 (1H 2,5 DIMETHYLPYRROL 1 YL)BENZOHYDRAZIDE; N' (1 METHYLBENZYLIDENE) 4 (1H 2,5 DIMETHYLPYRROL 1 YL)BENZOHYDRAZIDE; N' (PROPAN 2 YLIDENE) 4 (1H 2,5 DIMETHYLPYRROL 1 YL)BENZOHYDRAZIDE; NORFLOXACIN; OXADIAZOLE DERIVATIVE; PYRROLE DERIVATIVE; TRIAZOLE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BACILLUS SUBTILIS; BACTERIAL STRAIN; BROTH DILUTION; CANCER CELL CULTURE; CANDIDA TROPICALIS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; IN VITRO STUDY; INFRARED SPECTROSCOPY; KLEBSIELLA PNEUMONIAE; LUNG ADENOCARCINOMA; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; SACCHAROMYCES CEREVISIAE; STAPHYLOCOCCUS AUREUS; VERO CELL;

EID: 84874106227     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0112-0     Document Type: Article

References (27)

1. Biava M, Fioravanti R, Porretta GC, Deidda D, Maullu C, Pompei R (1999) New pyrrole derivatives as antimycobacterial agents analogs of BM 212. Biorg Med Chem Lett 9:2983-2988
2. Das RK (2000) Tuberculosis-historical landmarks. J Indian Med Assoc 98:112-114
3. Demirayak S, Karaburun AC, Kiraz N (1999) Synthesis and antibacterial activities of some 1-[2-(substituted pyrrol-1-yl)ethyl]-2-methyl-5- nitroimidazole derivatives. Eur J Med Chem 34:275-278
4. Demirayak S, Karaburun AC, Beis R (2004) Some pyrrole substituted aryl pyridazinone and phthalazinone derivatives and their antihypertensive activities. Eur J Med Chem 39:1089-1095
5. Desai NC, Shukla K, Thaker KA (1984) Some new 2-aryl-3-isonicotamido-4- thiazolidinones and their 5-carboxymethy homologues as potential antitubercular and antibacterial agents. J Indian Chem Soc 61:239-240
6. Desai B, Sureja D, Naliapara Y, Shah A, Saxena AK (2001) Synthesis and QSAR studies of 4-substituted phenyl-2,6-dimethyl-3, 5-bis-N-(substituted phenyl)carbamoyl-1,4-dihydropyridines as potential antitubercular agents. Bioorg Med Chem 9:1993-1998
7. Dutt AK, Stead WW (1999) In: David S (ed) Tuberculosis and nontuberculosis mycobacterial infections, 4th edn. W.B. Saunders, Pennsylvania, p 3
8. Dye C (2002). 4th World congress on tuberculosis, Washington, DC. June 3-5
9. Goto S, Jo K, Kawakita T, Mitsuhashi S, Nishino T, Ohsawa N, Tanami H (1981) Determination method of minimum inhibitory concentrations. Chemother Chemother 29:76-79
10. Gundersen LL, Nissen-Meyer J, Spilsberg B (2002) Synthesis and antimycobacterial activity of 6-arylpurines: the requirements for the N-9 substituent in active antimycobacterial purines. J Med Chem 45:1383-1386
11. Jones RA (1992) Pyrroles, part II, the chemistry of heterocyclic compounds, vol 48. Wiley, New York, pp 131-298
12. Jones RA, Bean GP (1997) The chemistry of pyrroles. Academic Press, London, pp 51-57
13. Joshi SD, Vagdevi HM, Vaidya VP, Gadaginamath GS (2008a) Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems, a novel class of potential antibacterial and antitubercular agents. Eur J Med Chem 43:1989-1996
14. Joshi SD, Vagdevi HM, Vaidya VP, Gadaginamath GS, Purohit SS (2008b) Synthesis and antibacterial and antitubercular activities of some new 3-substituted phenyl-5-(4-pyrrol-1-ylphenyl)-4H-1,2,4-triazole derivatives. Indian J Heterocycl Chem 17:367-368
15. Joshi SD, Joshi Ashwini, Vagdevi HM, Vaidya VP, Gadaginamath GS (2010) Microwave assisted synthesis of some new quinolinylpyrrole derivatives as potential antibacterial and antitubercular agents. Indian J Heterocycl Chem 19:221-224
16. Khalil MA, El-Sayed OA, El-Shamny HA (1993) Synthesis of certain 2-aminoadamantane derivatives as potential antimicrobial agents. Arch Pharm 326:489-492
17. Maher D, Floyd K, Raviglione M (2002) Strategic framework to decrease the burden of TB/HIV. World Health Organization, Geneva
18. Martien WB, Floyd K, Broekmans JF (2002) Interventions to reduce tuberculosis mortality and transmission in low- and middle-income countries. Bull World Health Organ 80:217-227
19. Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55-63
20. Rouhi AM (1999) Tuberculosis: a tough adversary. In Chem Eng News 77:52-70
21. Shah RR, Mehta RD, Parikh AR (1985) Studies on isoniazid derivatives. Preparation and antimicrobial activity of 2-aryl-3-(pyridylcarbomyl)-5- carboxymethyl-4-thiazolidinones. J Indian Chem Soc 62:255-257
22. Sriram D, Yogeeswari P, Madhu K (2005) Synthesis and in vitro antimycobacterial activity of some isonicotinoyl hydrazones. Bioorg Med Chem Lett 15:4502-4505
23. Sriram D, Yogeeswari P, Madhu K (2006) Synthesis and in vitro antitubercular activity of some 1-[(4-sub)phenyl]-3-(4-{1-[(pyridine-4-carbonyl) hydrazono]ethyl phenyl) thiourea. B. Bioorg Med Chem Lett 16:876-878
24. Suling WJ, Seitz LE, Pathak V, Westbrook L, Barrow EW, Ginkel SZV, Reynolds RC, Robert Piper J, Barrow WW (2000) Antimycobacterial activities of 2,4-diamino-5-deazapteridine derivatives and effects on mycobacterial dihydrofolate reductase. Antimicrob Agents Chemother 44:2784-2793
25. Suresh Kumar GV, Rajendraprasad Y, Mallikarjuna BP, Chandrashekar SM, Kistayya C (2010) Synthesis of some novel 2-substituted-5-[isopropylthiazole] clubbed 1,2,4-triazole and 1,3,4-oxadiazoles as potential antimicrobial and antitubercular agents. Eur J Med Chem 45:2063-2074
26. Vigorita MG, Maccari R, Ottana R, Monforte F (1999) Lipophilic analogs of isoniazid with antiproliferative in vitro activity. Med Chem Res 9:306-321
27. Yajko DM, Madej JJ, Lacaster MV, Sanders CA, Cawthon VL, Gee B, Babst A, Keith Hardley W (1995) Colorimetric method for determining MICs of antimicrobial agents for Mycobacterium tuberculosis. J Clin Microbiol 33:2324-2327