Synthesis of novel quinolone and coumarin based 1,3,4-thiadiazolyl and 1,3,4-oxadiazolyl N-mannich bases as potential antimicrobials

Letters in Organic Chemistry

Volumn 9, Issue 7, 2012, Pages 478-486

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

^a SARDAR VALLABHBHAI NATIONAL INSTITUTE OF TECHNOLOGY   (India)

^b GUJARAT UNIVERSITY   (India)

Author keywords

1,3,4 oxadiazole; 1,3,4 thiadiazole; Antimicrobial activity; Coumarin; Piperazine; Quinolone

Indexed keywords

EID: 84865804105     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017812802139681     Document Type: Article

References (42)

1. Okuma, K.; Iwakawa, K.; Turnidge, J.D.; Grubb, W.B.; Bell, J.M.; O'Brien, F.G.; Coombs, G.W.; Pearman, J.W.; Tenover, F.C.; Kapi, M.; Tiensasitorn, C.; Ito, T.; Hiramatsu, K. Dissemination of new methicillin-resistant Staphylococcus aureus clones in the community. J. Clin. Microbiol., 2002, 40, 4289-4294.
2. Klein, E.; Smith, D.L.; Laxminarayan, R. Hospitalizations and Deaths Caused by Methicillin-Resistant Staphylococcus aureus, United States, 1999-2005. Emerg. Infect. Dis., 2007, 13(12), 1840-1846.
3. Johnson, E.M.; Warnock, D.W.; Luker, J.; Portor, S.R.; Crispian, S.J. Emergence of azole drug resistance in Candida species from HIV-infected patients receiving prolonged fluconazole therapy for oral candidosis. Antimicrob. Chemother., 1995, 35(1), 103-114.
4. World Health Organization, Global tuberculosis control: a short update to the 2009 report. Available at http://www.who.int/tb/publications/globalreport/ 2009/update/en/index.htm.
5. Bakht, M.A.; Yar, M.S.; Abdel-Hamid, S.G.; Al Qasoumi, S.I.; Samad, A. Molecular properties prediction, synthesis and antimi-crobial activity of some newer oxadiazole derivatives. Eur. J. Med. Chem., 2010, 45(12), 5862-5869.
6. 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 sul-foxide derivatives containing trimethoxyphenyl substituted 1, 3, 4-thiadiazole and 1, 3, 4-oxadiazole moiety. Bioorg. Med. Chem., 2008, 16, 3632-3640.
7. 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(11), 4963-4967.
8. Khanum, S.A.; Shashikanth, S.; Umesh, S.; Kavitha, R. Synthesis and antimicrobial study of novel heterocyclic compounds from hy-droxybenzophenones. Eur. J. Med. Chem., 2005, 40(11), 1156-1162.
9. 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(11), 4708-4719.
10. 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. Syn-thesis and antifungal activities of 5-(3, 4, 5-trimethoxyphenyl)-2-sulfonyl-1, 3, 4-thiadiazole and 5-(3, 4, 5-trimethoxyphenyl)-2-sulfonyl-1, 3, 4-oxadiazole derivatives. Bioorg. Med. Chem., 2007, 15(11), 3981-3989.
11. Mamolo, M.G.; Zampieri, D.; Vio, 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(11), 3797-3809.
12. 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(3), 197-206.
13. Ali, M.A.; Shaharyar, M. Oxadiazole mannich bases: Synthesis and antimycobacterial activity Bioorg. Med. Chem. Lett., 2007, 17, 3314-3316.
14. Desai, K.; Baxi, A.J. Studies on 2-azetidinone: part vi synthesis and antimicrobial activity of 5-(2', 4'-dichlorophenoxymethyl)-2-(4"-aryl- 3"-chloro-2"-azetidinone-1"-yl)-1, 3, 4-thiadiazole. Indian J. Pharm. Sci., 1992, 54, 183-188.
15. Gawande, N.G.; Shingare, M.S. Synthesis of some thiazolylthiosemicarbazides. triazoles, oxadiazoles, thiadiazoles & their microbial activity. Indian J. Chem., 1987, 26, 387-389.
16. Mamolo, M.G.; Vio, L.; Banfi, E. Synthesis and antimicrobial activity of some 2, 5-disubstituted 1, 3, 4-thiadiazole derivatives. Farmaco., 1996, 51, 71-74.
17. Shucla, H.K.; Desai, N.C.; Astik, R.R.; Thaker, K.A. Studies on some thiosemicarbazones and 1, 3, 4-thiadiazoles as potential antitu-bercular and antibacterial agents. J. Indian Chem. Soc., 1984, 61, 168-171.
18. Miyamoto, K.; Koshiura, R.; Mori, M.; Yokoi, H.; Mori, C.; Hasegawa, T.; Takatori, K. Antitumour activity 5-substituted 2-acylamino-1, 3, 4thiadiazole against transplantable rodent tumours. Chem. Pharm. Bull., 1985, 33, 5126-5129.
19. Chou, J.Y.; Lai, S.Y.; Pan, S.L., Jow, G.M., Chern, J.W., Guh, J.H. Investigation of anticancer mechanism of thiadiazole based com-pound in human nonsmall cell lung cancer A549 cells. Biochem. Pharmacol., 2003, 66, 115-124.
20. Singh, A.K.; Mishra G.; Jyoti, K. Review on Biological Activities of 1, 3, 4-Thiadiazole Derivatives. J. Appl. Pharm. Sci., 2011, 01, 44-49.
21. Nagaraj; Chaluvaraju, K.C.; Niranjan, M.S.; Kiran S. 1, 1, 3, 4 oxadiazole: a potent drug candidate with various pharmacological Activities. Int. J. Pharm. Pharm. Sci., 2011, 3, 9-16.
22. Boschelli, D.H.; Connor, D.T.; Bornemeier, D.A.; Dyer, R.D.; Kennedy, J.A.; Kuipers, P.J.; Okonkwo, G.C.; Schrier, D.J.; Wright, C.D. 1, 3, 4-Oxadiazole, 1, 3, 4-thiadiazole, and 1, 2, 4-triazole analogs of the fenamates: in vitro inhibition of cyclooxygenase and 5-lipoxygenase activities. J. Med. Chem., 1993, 36, 1802-1810.
23. Nargund, L.V.; Reddy, G.R.; Hariprasad, V. Anti-inflammatory activity of substituted 1, 3, 4-oxadiazoles.J Pharm Sci., 1994, 83(2), 246-248.
24. Ksepko, D.P.; Foks, H.; Janowiec, H.; Kwiek, Z.Z. Synthesis and tuberculostatic activity of reaction products 5-(2-, 3-and 4-pyridil)-1, 3, 4-oxadiazol-2-thione with amines. Acta. Pol. Pharm., 1993, 50, 259-267.
25. Mishra, A.R.; Singh, S. Antifungal Activity of New 1, 3, 4-oxadiazolo[3, 2-a]-s-triazine-5, 7-diones and Their 5-thioxo-7-ones. J. Agric. Food Chem., 2000, 48 (11), 5465-5468.
26. Mazonne, G.; Bonina F. Synthesis and antimycotic activity of 3-methylamino derivatives of various 2-mercapto-5-aryl-1, 3, 4-oxadiazoles. Farmaco. Ed. Sci., 1979, 34, 390-342.
27. Aggarwal, N.; Kumar, R; Dureja, P.; Khurana, J. M. Synthesis of novel nalidixic acid based 1, 3, 4-thiadiazole and 1, 3, 4-oxadiazole derivatives as potent antibacterial agents, Chemical biology & Drug Design. Chem. Bio. & Drug Design, DOI: 10.1111/j.1747-0285.2011.01316.x.
28. Vukovic, N.; Sukdolak, S.; Solujic, S.; Niciforovic, N. Substituted imino and amino derivatives of 4-hydroxycoumarins as novel anti-oxidant, antibacterial and antifungal agents: Synthesis and in vitro assessments. Food Chem., 2010, 120(4), 1011-1018.
29. Mladenovic, M.; Vukovic, N.; Niciforovic, N.; Sukdolak, S.; Solu-jic, S. Synthesis and molecular descriptor characterization of novel 4-hydroxy-chromene-2-one derivatives as antimicrobial agents. Molecules, 2009, 14(4), 1495-1512.
30. Vukovic, N.; Sukdolak, S.; Solujic, S.; Milosevic, T. Synthesis and Antimicrobial Evaluation of Some Novel 2-Aminothiazole Deriva-tives of 4-Hydroxy-chromene-2-one. Arch. Pharm. Chem. Life Sci., 2008, 341(8), 491-496.
31. 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.
32. Patel, R.V.; Kumari, P.; Rajani, D.P.; Chikhalia, K.H. Fluorinated s-triazinyl piperazines as antimicrobial agents. Z Naturforsch C. J. Biosci., 2011, 66, 341-345.
33. 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 antimicro-bial/antimycobacterial activity. J. Enzyme Inhib. Med. Chem., 2012, 27, 370-379.
34. 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 po-tential antimicrobial, antimycobacterial and anticancer agents. Eur. J. Med. Chem., 2011, 46, 4354-4365.
35. Chitre, T.S.; Panda, S.; Patil, S.M.; Chothe, A.S.; Vignesh, G.; Salake, A.B.; Kathiravan, M.K. Novel 1, 3, 4-(thiadiazol-2-ylamino) methyl-5-(pyridin-4- yl)-1, 3, 4-oxadiazol-2-thiones: synthesis, dock-ing and antimycobacterial testing. Adv. in Bio. Chem., 2011, 1, 7-14.
36. Al-Omar, M.A. Synthesis and Antimicrobial Activity of New 5-(2-Thienyl)-1, 2, 4-triazoles and 5-(2-Thienyl)-1, 3, 4-oxadiazoles and Related Derivatives. Molecules, 2010, 15, 502-514.
37. Mayekar, A.N. Synthesis and Antimicrobial Studies on New Sub-stituted 1, 3, 4-Oxadiazole Derivatives Bearing 6-Bromonaphthalene Moiety. Int. J. Chem., 2010, 2, 38-54.
38. Panda, S.S.; Malik, R.; Chand, M; Jain, S.C. Synthesis and antimi-crobial activity of some new 4-triazolylmethoxy-2H-chromen-2-one derivatives. Med Chem. Res. DOI 10.1007/s00044-011-9881-0.
39. 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., DOI 10.1007/s00044-012-0026-x.
40. 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 antitu-berculosis agents. Eur. J. Med. Chem., 2012, 53, 41-51.
41. Chimichi, S.; Boccalini, M.; Cosimelli, B. A new convenient route to 2-oxoethoxycoumarins: key intermediates in the synthesis of natural products. Tetrahedron, 2002, 58, 4851-4858.
42. Clause, G.W. Understanding microbes: A laboratory textbook for microbiology; W.H. Freeman and Company: New York, USA, 1989.