Synthesis of some oxadiazole derivatives as new anticandidal agents

Molecules

Volumn 16, Issue 9, 2011, Pages 7662-7671

  Kaplancikli, Zafer Asim ^a  

^a ANADOLU UNIVERSITY   (Turkey)

Author keywords

Anticandidal activity; Oxadiazole; Pyrimidine

Indexed keywords

5 ((PYRIMIDIN 2 YLTHIO)METHYL) 1,3,4 OXADIAZOLE 2(3H) THIONE; 5-((PYRIMIDIN-2-YLTHIO)METHYL)-1,3,4-OXADIAZOLE-2(3H)-THIONE; ANTIFUNGAL AGENT; OXADIAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE; SULFIDE;

ARTICLE; CANDIDA ALBICANS; CHEMISTRY; DRUG EFFECT; MICROBIOLOGICAL EXAMINATION; SYNTHESIS;

ANTIFUNGAL AGENTS; CANDIDA ALBICANS; MICROBIAL SENSITIVITY TESTS; OXADIAZOLES; PYRIMIDINES; SULFIDES;

EID: 80053279167     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16097662     Document Type: Article

References (24)

1. Ruan, S.Y.; Hsueh, P.R. Invasive Candidiasis: An Overview from Taiwan. J. Formos. Med. Assoc. 2009, 108, 443-451.
2. Canuto, M.M.; Rodero, F.G. Antifungal drug resistance to azoles and polyenes. Lancet Infect. Dis. 2002, 2, 550-563. (Pubitemid 34966358)
3. Ghannoum, M.A.; Louis, B.R. Antifungal Agents: Mode of Action, Mechanisms of Resistance and Correlation of These Mechanisms with Bacterial Resistance. Clin. Microbiol. Rev. 1999, 12, 501-517. (Pubitemid 29484744)
4. Pfaller, M.A.; Diekema, D.J. Epidemiology of Invasive Candidiasis: A Persistent Public Health Problem. Clin. Microbiol. Rev. 2007, 20, 133-163. (Pubitemid 46167771)
5. Sheehan, D.J.; Hitchcock, C.A.; Sibley, C.M. Current and emerging azole antifungal agents. Clin. Microbiol. Rev. 1999, 12, 40-79. (Pubitemid 29055953)
6. Jiang, L.; Tan Y.; Zhu, X.; Wang, Z.; Zuo, Y.; Chen, Q.; Xi, Z.; Yang, G. Design, Synthesis, and 3D-QSAR Analysis of Novel 1,3,4-Oxadiazol-2(3H)-ones as Protoporphyrinogen Oxidase Inhibitors. J. Agric. Food Chem. 2010, 58, 2643-2651.
7. Mayekar, A.N.; Yathirajan, H.S.; Narayana, B.; Sarojini, B.K.; Suchetha Kumari, N. Synthesis and Antimicrobial Studies on New Substituted 1,3,4-Oxadiazole Derivatives Bearing 6-Bromonaphthalene Moiety. Int. J. Chem. 2010, 2, 38-54.
8. Farshori, N.N.; Banday, M.R.; Ahmad, A.; Khan, A.U.; Rauf, A. Synthesis, characterization, and in vitro antimicrobial activities of 5-alkenyl/ hydroxyalkenyl-2-phenylamine-1,3,4-oxadiazoles and thiadiazoles. Bioorg. Med. Chem. Lett. 2010, 20, 1933-1938.
9. Chikhalia, K.H.; Vashi, D.B.; Patel, M.J. Synthesis of a novel class of some 1,3,4-oxadiazole derivatives as antimicrobial agents. J. Enzym. Inhib. Med. Chem. 2009, 24, 617-622.
10. Karabasanagouda, T.; Adhikari, A.V.; Shetty, N.S. Synthesis and Antimicrobial Activities of Some novel 1,3,4-Oxadiazoles Carrying Alkylthio and Alkylsulphonylphenoxy Moieties. Phosphor. Sulfur Silicon 2007, 182, 2925-2941.
11. Bakht, M.A.; Shahar Yar, M.; Abdel-Hamid, S.G.; Al 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. Bala, S.; Kamboj, S.; Kumar, A. Heterocyclic 1,3,4-oxadiazole compounds with diverse biological activities: A comprehensive review. J. Pharm. Res. 2010, 3, 2993-2997.
13. Padmavathi, V.; Sudhakar Reddy, G.; Padmaja, A.; Kondaiah, P.; Shazia, A. Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. Eur. J. Med. Chem. 2009, 44, 2106-2112.
14. Dolman, S.J.; Gosselin, F.; O'Shea, P.D.; Davies, I.W. Superior Reactivity of Thiosemicarbazides in the Synthesis of 2-Amino-1,3,4-oxadiazoles. J. Org. Chem. 2006, 71, 9548-9551. (Pubitemid 44924549)
15. Horning, D.E.; Muchowski, J.M. Five-membered Heterocyclic Thiones. Part I. 1,3,4-Oxadiazole-2-thione. Can. J. Chem. 1972, 50, 3079-3082.
16. Mekuskiene, G.; Burbuliene, M.M.; Jakubkiene, V.; Udrenaite, E.; Gaidelis, P.; Vainilavicius, P. 5-(4,6-diphenyl-2-pyrimidinyl)-1,3,4-oxadiazole- 2-thione with some C-electrophiles and N nucleophiles. Chem. Heterocycl. Comp. 2003, 39, 1364-1368.
17. Kalluraya, B.; Lingappa, B.; Nooji, S.R.; Kumari, N.S. Regioselective reaction: synthesis of novel Mannich bases derived from 5-(4,6-disubstituted-2- thiomethyl pyrimidyl)-1,3,4-oxadiazole-2-thiones and their biological properties. Org. Chem. Indian J. 2006, 2, 158-164.
18. Liu, T.T.; Lee, R.E.B.; Barker, K.S.; Lee, R.E.; Wei, L.; Homayouni, R.; Rogers P.D. Genome-wide expression profiling of the response to azole, polyene, echinocandin, and pyrimidine antifungal agents in Candida albicans. Antimicrob. Agents Ch. 2005, 49, 2226-2236. (Pubitemid 40734449)
19. Shadomy, S.; Kirchoff, C.B.; Ingroff A.E. In vitro activity of 5-fluorocytosine against Candida and Torulopsis species. Antimicrob. Agents Ch. 1973, 3, 9-14.
20. Gülerman, N.N.; Dogan, H.N.; Rollas, S.; Johansson, C.; Çelik, C. Synthesis and structure elucidation of some new thioether derivatives of 1,2,4-triazoline-3-thiones and their antimicrobial activities. Farmaco 2001, 56, 953-958. (Pubitemid 34019225)
21. Dhayanithi, V.; Syed, S.S.; Kumaran, K.; Sankar, K.R.J.; Ragavan, R.V.; Goud, P.S.K.; Kumari, N.S.; Pati, H.N. Synthesis of selected 5-thio-substituted tetrazole derivatives and evaluation of their antibacterial and antifungal activities. J. Serb. Chem. Soc. 2011, 76, 165-175.
22. Beggs, W.H. Influence of growth phase on the susceptibility of Candida albicans to butoconazole, oxiconazole, and sulconazole. J. Antimicrob. Chemoth. 1985, 16, 397-399. (Pubitemid 15016618)
23. Koneman, E.W.; Allen, S.D.; Janda, W.M.; Schreckenberger, P.C.; Winn, W.C. Color Atlas and Textbook of Diagnostic Microbiology, 5th ed.; Lippincott-Raven: Philadelphia, PA, USA, 1997; pp. 785-856.
24. Özdemir, A.; Turan-Zitouni, G.; Kaplancikli, Z.A.; Iscan, G.; Khan, S.; Demirci, F. Synthesis and the selective antifungal activity of 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine derivatives. Eur. J. Med. Chem. 2010, 45, 2080-2084