Synthesis and biological activity of 5-substituted-2-amino-1,3,4-oxadiazole derivatives

Electrical energy offers numerous benefits for performing synthesis, including increased reaction rates, enhanced yields, and cleaner chemistries. 5-Substituted-2-amino-1,3,4-oxadiazoles were synthesized directly from the semicarbazone at a platinum electrode under controlled potential electrolysis in an undivided cell assembly in acetonitrile. The compounds were screened for antibacterial and antifungal activity against Staphylococcus aureus, Klebsiella pneumoniae, Pellicularia salmonicolor, and Macrophomina phaseolina.

Anahtar Kelimeler:

Antibacterial, antifungal, controlled potential, electrolysis, platinum electrode

Synthesis and biological activity of 5-substituted-2-amino-1,3,4-oxadiazole derivatives

Keywords:

Antibacterial, antifungal, controlled potential, electrolysis, platinum electrode,

PDF

___

1. Holla, B. S.; Gonaslaves, R.; Shenoy, S. Eur. J. Med. Chem. 2000, 35, 267-271.
2. Cesur, N.; Birteksoz, S.; Otuk, G. Acta Pharm. Turc. 2002, 44, 23-41.
3. Laddi, U. V.; Desai, S. R.; Bennur, R. S.; Bennur, S. C. Indian J. Heterocyclic Chem. 2002, 11, 319-322.
4. Zou, X.; Zhang, Z.; Jin, G. J. Chem. Res. (S) 2002, 228-230.
5. Zou, X. J.; Lai, L. H.; Jin, G. Y.; Zhang, Z. X. J. Agric. Food Chem. 2002, 50, 3757-3760.
6. Palaska, E.; Sohin, G.; Kalicen, P.; Darlu, N. T.; Altinok, G. Farmaco 2002, 57, 101-107.
7. Tyagi, M.; Kumar, A. Orient. J. Chem. 2002, 18, 125-130.
8. Hetzheim, A.; Moeckel, K. Adv. Heterocyclic Chem. 1966, 7, 183-224.
9. Hill, J. In Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; Pergamon Press, Oxford, 1984.
10. Chiba, T.; Okimoto, M. J. Org. Chem. 1992, 57, 1375-1379.
11. Butler, R. N.; Scott, F. L.; O’Mahony, T. A. F. Chem. Rev. 1973, 73, 93-102.
12. Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
13. Adams, G. L.; Graybill, T. L.; Sanchez, R. M.; Magard, V. W.; Burton, G.; Rivero, R. A. Tetrahedron Lett. 2003, 44, 5041-5045.
14. Tori, S. Electroorganic Syntheses, Kodansha, Tokyo, 1985.
15. Aboulwafa, O. M.; Omar, O. M. M. E. Sulfur Lett. 1992, 14, 181-188.
16. Omar, F. A.; Mahfouz, N. M.; Rahman, M. A. Eur. J. Med. Chem. 1996, 31, 819-825.
17. Golovlyova, S. M.; Moskvichev, Y. A.; Alov, E. M.; Kobylinskey, D. B.; Ermolaeva, V. V. Chem. Heterocycl. Compd. 2001, 37, 1102-1106.
18. Liu, F. M.; Wang, B. L.; Zhang, Z. F. Youji Huaxue 2001, 21, 1126-1131.
19. Gani, R. S.; Pujar, R. S.; Gadaginamath, G. S. Indian J. Heterocycl. Chem. 2002, 12, 25-28.
20. Wang, X.; Li, Z.; Yang, J. Synth. Commun. 2002, 32, 1097-1103.
21. Brain, C. T.; Brunton, S. A. Synlett 2001, 382-384.
22. Brain, C. T.; Paul, J. M.; Loong, Y.; Oakley, P. J. Tetrahedron Lett. 1999, 40, 3275-3278.
23. Faidallah, H. M.; Sharshira, E. M.; Basaif, S. A.; A-Ba-Oum, A. E. Phosphorus Sulfur Silicon 2002, 177, 67.
24. Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2001, 42, 2583-2586.
25. Brown, B. J.; Clemens, I. R.; Neesom, J. K. Synlett 2000, 131-133.
26. Cappo, F. T.; Evans, K. A.; Graybill, T. L.; Burton, G. Tetrahedron Lett. 2004, 45, 3257-3260.
27. Shono, T. Electroorganic Synthesis, Academic Press, London, 1991.
28. Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Nonaqueous Systems, Marcel Dekker, New York, 1970.
29. Fry, A. J. Synthetic Organic Electrochemistry, 2nd ed., Wiley-Interscience, New York, 1989.
30. Singh, S.; Kumar, S.; Sharma, L. K.; Singh, R. K. P. J. Indian Chem. Soc. 2009, 86, 734-738.
31. Sharma, L. K.; Kumar, S.; Yadav, P.; Singh, R. K. P. Indian J. Chem., Sec. B 2008, 47, 1277-1280.
32. Sharma, L. K.; Kumar, S.; Singh, S.; Singh, R. K. P. Russian J. Electrochem. 2010, 46, 34-40.
33. Murthy, G. R.; Rao, A. B.; Reddy, V. M.; Sisodia, P. Indian Drugs 1986, 23, 354-357.
34. Yale, H. L.; Losee, K. J. Med. Chem. 1966, 9, 478-483.
35. Hejsek, M.; Wiedermannova, I. Acta Universitatis Palackianae Olomucensis, Facultas Rerum Naturalium, Chemica 2001, 40, 15-24.
36. Benson, H. J. Microbiological Applications, 5th ed., W. C. Brown Publications, Boston, 1990.
37. Vincent, J. C.; Vincent, H. W. Proc. Soc. Expt. Biol. Medi. 1944, 55, 162-164.