New quinolinyl-1,3,4-oxadiazoles: Synthesis, in vitro antibacterial, antifungal and antituberculosis studies

Medicinal Chemistry

Volumn 9, Issue 4, 2013, Pages 596-607

  Patel, Rahul V ^a   Kumari, Premlata ^a   Chikhalia, Kishor H ^b  

^a SARDAR VALLABHBHAI NATIONAL INSTITUTE OF TECHNOLOGY   (India)

^b GUJARAT UNIVERSITY   (India)

Author keywords

5 quinolinyl 6 yl 1,3,4 oxadiazol 2 thiol; Antimicrobial activity; Antituberculosis activity; Benzothiazole; Quinoline 6 carboxylic acid

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO) N P TOLYLACETAMIDE; 5 QUINOLIN 6 YL 1,3,4 OXADIAZOL 2 THIOL; CARBON DISULFIDE; ESTER DERIVATIVE; HYDRAZINE; N (4 ACETAMIDOPHENYL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (4 BROMOPHENYL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (4 CHLOROPHENYL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (4 CYANOPHENYL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (4 ETHOXYPHENYL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (4 FLUOROPHENYL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (4 IODOPHENYL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (4 METHOXYPHENYL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (4 NITROPHENYL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2YLTHIO)ACETAMIDE; N (6 BROMOBENZO[D]THIAZOL 2 YL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (6 CHLOROBENZO[D]THIAZOL 2 YL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (6 CYANOBENZO[D]THIAZOL 2 YL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (6 FLUOROBENZO[D]THIAZOL 2 YL) 2 (5 (QUINOLIN 6 YL)1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (6 IODOBENZO[D]THIAZOL 2 YL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (6 METHYLBENZO[D]THIAZOL 2 YL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (6 NITROBENZO[D]THIAZOL 2 YL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (BENZO[D]THIAZOL 2 YL) 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; N (BENZO[D]THIAZOL 2 YL) 2 CHLOROACETAMIDE DERIVATIVE; N PHENYL 2 (5 (QUINOLIN 6 YL) 1,3,4 OXADIAZOL 2 YLTHIO)ACETAMIDE; QUINOLINE 6 CARBOHYDRAZIDE; QUINOLINE 6 CARBOXYLIC ACID METHYL ESTER; QUINOLYL 1,3,4 OXADIAZOL 2YLTHIO N BENZOTHIAZOLYL ACETAMIDE DERIVATIVE; QUINOLYL 1,3,4 OXADIAZOL 2YLTHIO N PHENYL ACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS CLAVATUS; ASPERGILLUS FUMIGATUS; ASPERGILLUS NIGER; BACILLUS CEREUS; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; INFRARED RADIATION; KLEBSIELLA PNEUMONIAE; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; PROTEUS VULGARIS; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; SALMONELLA TYPHI; SHIGELLA FLEXNERI; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ANTITUBERCULAR AGENTS; FUNGI; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MICROBIAL SENSITIVITY TESTS; OXADIAZOLES; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84877950215     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/1573406411309040014     Document Type: Article

References (36)

1. Nathan, C. Antibiotics at the crossroads. Nature, 2004, 431, 899- 902.
2. World Health Organization, Global tuberculosis control: a short update to the 2009 report. Available at http://www.who.int/tb/publications/global-report/ 2009/update/en/index.html.
3. Patel, R.V.; Kumari, P.; Rajani, D.P.; Chikhalia, K.H. A new class of 2-(4-cyanophenyl amino)-4-(6-bromo-4-quinolinyloxy)-6- piperazinyl(piperidinyl)- 1, 3, 5-triazine analogues with antimicrobial/antimycobacterial activity. J. Enzyme Inhib. Med. Chem., 2012, 27, 370-379.
4. Patel, R.V.; Kumari, P.; Chikhalia, K.H. Fluorinated s-triazinyl piperazines as antimicrobial agents. Z. Naturforsch. C., 2011, 66C, 345-352.
5. Patel, R.V.; Kumari, P.; Rajani, D.P.; Chikhalia, K.H. Synthesis, characterization and pharmacological activities of 2- [4-cyano-(3- trifluoromethyl)phenyl amino)]-4-(4-quinoline/coumarin-4-yloxy)- 6- (fluoropiperazinyl)-s-triazines. J. Fluorine Chem., 2011, 132, 617-627.
6. Musiol, R.; Jampilek, J.; Buchta, V.; Silva, L.; Niedbala, H.; Podeszwa, B.; Palka, A.; Majerz-Maniecka, K.; Oleksyn, B.; Polanski, J. Antifungal properties of new series of quinoline derivatives. Bioorg. Med. Chem., 2006, 14, 3592-3598.
7. Charris, J.; Dominguez, J.; Gamboa, N.; Rodrigues, J.; Angel, J. Synthesis and antimalarial activity of E-2- quinolinylbenzocycloalcanones. Eur. J. Med. Chem., 2005, 40, 875-881.
8. Patel, R.V.; Kumari, P.; Rajani, D.P.; Chikhalia, K.H. Synthesis and antimycobacterial activity of various 1-(8-quinolinyloxy)-3- piperazinyl(piperidinyl)-5-(4-cyano-3-trifluoromethylphenyl amino)-s-triazines. Acta Chim. Slov., 2011, 58, 802-810.
9. Zhao, Y.; Chen, Y.; Chang, F.; Tzeng, C. Synthesis and cytotoxic evaluation of certain 4-anilino-2-phenylquinoline derivatives. Eur. J. Med. Chem., 2005, 40, 792-797.
10. Patel, R.V.; Kumari, P.; Rajani, D.P.; Pannecouque, C.; De Clercq, E., Chikhalia, K.H. Antimicrobial, antituberculosis, anticancer and anti-HIV evaluation of newer s-triazine based heterocycles. Fut. Med. Chem., 2012, 4, 1053-1065.
11. Mohammed, A.B.; Yar, M.S.; Abdel-Hamid, S.G.; Qasoumi, S.I.; Samad, A. Molecular properties prediction, synthesis and antimicrobial activity of some newer oxadiazole derivatives. Eur. J. Med. Chem., 2010, 45, 5862-5869.
12. Liu, F.; Luo, X.Q.; Song, B.A.; Bhadury, P.S.; Yang, S.; Jin, L.H.; Xue, W.; Hu, D.Y. Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1, 3, 4- thiadiazole and 1, 3, 4-oxadiazole moiety. Bioorg. Med. Chem., 2008, 16, 3632-3640.
13. Jha, K.K.; Samad, A.; Kumar, Y.; Shaharyar, M.; Khosa, R.L.; Jain, J.; Kumar, V.; Singh, P. Design, synthesis and biological evaluation of 1, 3, 4-oxadiazole derivatives. Eur. J. Med. Chem., 2010, 45, 4963-4967.
14. Naveena, C.S.; Boja, P.; Kumari, N.S. Synthesis, characterization and antimicrobial activity of some disubstituted 1, 3, 4-oxadiazoles carrying 2-(aryloxymethyl)phenyl moiety. Eur. J. Med. Chem., 2010, 45, 4708-4719.
15. Chen, C.J.; Song, B.A.; Yang, S.; Xu, G.F.; Bhadury, P.S.; Jin, L.H.; Hu, D.Y.; Li, Q.Z.; Liu, F.; Xue, W.; Lu, P.; Chen, Z. Synthesis and antifungal activities of 5-(3, 4, 5-trimethoxyphenyl)-2- sulfonyl-1, 3, 4-thiadiazole and 5-(3, 4, 5-trimethoxyph-enyl)-2- sulfonyl-1, 3, 4-oxadiazole derivatives. Bioorg. Med. Chem., 2007, 15, 3981-3989.
16. Mamolo, M.G.; Zampieri, D.; Voi, L.; Fermeglia, M.; Ferrone, M.; Pricl, S.; Scialinoc, G.; Banfi, E. Antimycobacterial activity of new 3-substituted 5-(pyridin-4-yl)-3H-1, 3, 4-oxadiazol-2-one and 2- thione derivatives. Preliminary molecular modeling investigations. Bioorg. Med. Chem., 2005, 13, 3797-3808.
17. Kucukguzel, S.G.; Oruc, E.E.; Rollas, S.; Sahin, F.; Ozbek, A. Synthesis, characterisation and biological activity of novel 4- thiazolidinones, 1, 3, 4-oxadiazoles and some related compounds. Eur. J. Med. Chem., 2002, 37, 197-206.
18. Ali, M.A.; Shaharyar, M. Oxadiazole mannich bases: synthesis and antimycobacterial activity. Bioorg. Med. Chem. Lett., 2007, 17, 3314-3316.
19. Aboraia, A.; Rahman, H.M.A.; Mahfuz, N.; Mohmoud, A.; Gendy, E.L. Novel 5-(2-hydroxyphenyl)-3-substituted-2, 3-dihydro-1, 3, 4- oxadiazole-2-thione derivatives: Promising anticancer agents. Bioorg. Med. Chem., 2006, 14, 1236-1246.
20. Patel, R.V.; Patel, P.K.; Kumari, P.; Rajani, D.P.; Chikhalia, K.H. Synthesis of benzimidazolyl-1, 3, 4-oxadiazol-2ylthio-N-phenyl (benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents. Eur. J. Med. Chem., 2012, 53, 41-51.
21. Saitoh, M.; Kunitomo, J.; Kimura, E.; Hayase, Y.; Kobayashi, H.; Uchiyama, N.; Kawamoto, T.; Tanaka, T.; Mol, C.D.; Dougan, D.R.; Textor, G.S.; Snell, G.P.; Itoh, F. Design, synthesis and structure- activity relationships of 1, 3, 4-oxadiazole derivatives as novel inhibitors of glycogen synthase kinase-3β. Bioorg. Med. Chem., 2009, 17, 2017-2029.
22. Patel, R.V.; Patel, J.K.; Kumari, P.; Chikhalia, K.H. Combination of bioactive moieties with different heteroatom(s): Application of Suzuki cross coupling reaction. Heteroatom Chem., 2012, 23, 399- 410.
23. Patel, R.V.; Patel, J.K.; Kumari, P.; Chikhalia, K.H. Synthesis of novel quinolone and coumarin based 1, 3, 4-thiazdiazolyl and 1, 3, 4- oxadiazolyl N-Mannich bases as potential antimicrobials. Lett. Org. Chem., 2012, 9, 478-486.
24. Patel, R.V.; Kumari, P.; Chikhalia, K.H. Synthesis of novel 3-(5- sulfanyl-1, 3, 4-oxadiazol-2-yl)-2H-chromen-2-one condensed striazinyl piperazines and piperidines as antimicrobial agents. Med. Chem. Res., 2012, 21, 3119-3132.
25. Akhtar, T.; Hameed, S.; Al-Masoudi, N.A.; Loddo, R.; La Colla, P. In vitro antitumour and antiviral activities of new benzothiazoles and 1, 3, 4-oxadiazole-2-thione derivatives. Acta Pharm., 2008, 58, 135-149.
26. Sawhney, S.N.; Boykin, D.W. Transmission of substituent effects in heterocyclic systems by carbon-13 nuclear magnetic resonance: Benzothiazoles. J. Org. Chem., 1979, 44, 1136-1142.
27. Patel, R.V.; Kumari, P.; Rajani, D.P.; Chikhalia, K.H. Synthesis of coumarin-based 1, 3, 4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides as antimicrobial and antituberculosis agents. Med. Chem. Res., in press, 2012, DOI 10.1007/s00044-012-0026-x.
28. Gillespie, S.H. Medical microbiology-Illustrated, Butterworth Heinemann Ltd., United Kingdom, 1994, 234-247.
29. Hawkey, P.M.; Lewis, D.A. Medical bacteriology- a practical approach. Oxford University Press, United Kingdom, 1994, 181- 194.
30. Anargyros, P.; Astill, D.S.; Lim, I.S. Comparison of improved BACTEC and Lowenstein-Jensen media for culture of mycobacteria from clinical specimens. J. Clin. Microbiol., 1990, 28, 1288- 1291.
31. Isenberg, H.D. Clinical microbiology procedures handbook, vol. 1, American Society for Microbiology, Washington, D.C., 1992.
32. Patel, R.V.; Kumari, P.; Rajani, D.P.; Chikhalia, K.H. Synthesis and studies of novel 2-(4-cyano-3-trifluoromethylphenyl amino)-4- (quinoline-4-yloxy)-6-(piperazinyl/piperidinyl)-s-triazines as potential antimicrobial, antimycobacterial and anticancer agents. Eur. J. Med. Chem. 2011, 46, 4354-4365.
33. Baraldi, P.G.; Preti, D.; Tabrizi, M.A.; Fruttarolo, F.; Saponaro, G.; Baraldi, S.; Romagnoli, R.; Moorman, A.R.; Gessi, S.; Varani, K.; Borea, P.A. N(6)- [(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxyphenyl]-( 2-chloro)-5'-N- ethylcarboxamido-adenosines: the first example of adenosine-related structures with potent agonist activity at the human A(2B) adenosine receptor. Bioorg. Med. Chem., 2007, 15, 2514-2527.
34. Wang, M.; Gao, M.; Mock, B.H.; Miller, K.D.; Sledge, G.W.; Hutchinsa, G.D.; Zhenga, Q.H. Synthesis of carbon-11 labeled fluorinated 2-arylbenzothiazoles as novel potential PET cancer imaging agents. Bioorg. Med. Chem., 2006, 14, 8599-8607.
35. Rana, A.; Siddiqui, N.; Khan, S.A.; Haque, S.E.; Bhat, M.A. N- { [(6-substituted-1, 3-benzothiazole-2-yl)amino]carbonothioyl}-2/4- substituted benzamides: synthesis and pharmacological evaluation. Eur. J. Med. Chem., 2008, 43, 1114-1122.
36. Amin, K.M.; Rahman, D.E.A.; Al-Eryani, Y.A. Synthesis and preliminary evaluation of some substituted coumarins as anticonvulsant agents. Bioorg. Med. Chem., 2008, 16, 5377-5388.