Valentina PAVIC, Maja MOLNAR, Tihomir KOVAC, Elizabeta HAS-SCHÖN, Ana AMIC, Marija KOVAC

Biological study on novel coumarinyl 1,3,4-oxadiazoles

Coumarinyl 1,3,4-oxadiazoles were synthesized from Schiff bases and acetic anhydride. All compounds were characterized by melting points and their structures con rmed by mass and 1 H and 13 C NMR spectrometry. These novel coumarinyl derivatives were subjected to antibacterial, antifungal, anta atoxigenic, and antioxidant activity. Their activity varied depending on their structure, where 2-(3-acetyl-5-(((4-methyl-2-oxo-2 H -chromen-7-yl)oxy)methyl)- 2,3-dihydro-1,3,4-oxadiazol-2-yl)-1,4-phenylene diacetate showed signi cant antioxidant and antibacterial activity on B. subtilis. 4-(3-Acetyl-5-(((4-methyl-2-oxo-2 H -chromen-7-yl)oxy)methyl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)-1,2-phenylene diacetate was found to possess excellent antifungal and antia atoxigenic activity.

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1. Bhatia, S.; Gupta, M. J. Chem. Pharm. Res . 2011 , 3 , 137-147.
2. de Oliveira, C. S.; Lira, B. F.; Barbosa-Filho, J. M.; Lorenzo, J. G. F.; de Athayde-Filho, P. F. Molecules 2012 , 17 , 10192-10231.
3. Raval, P. J.; Tarunkumar, A. N.; Dhaval, J. M.; Kruti, M. N.; Nilesh, P. H. J. Saudi Chem. Soc . 2014 , 18 , 101-106.
4. Spink, E.; Ding, D.; Peng, Z.; Boudreau, M. A.; Leemans, E.; Lastochkin, E.; Song, W.; Lichtenwalter, K.; O'Daniel, P. I.; Testero, S. A.; et al. J. Med. Chem. 2015 , 58 , 1380-1389.
5. 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.; et al. Bioorg. Med. Chem . 2007 , 15 , 3981-3989.
6. Zhang, K.; Wang, P.; Xuan, L. N.; Fu, X.; Fen, J.; Sha, L.; Liu, Y.; Chen, B. Bioorg. Med. Chem. Lett . 2014 , 24 , 5154-5156.
7. Dolman, S. J.; Gosselin, F.; O'Shea, P. D.; Davies, I. W. J. Org. Chem . 2006 , 71 , 9548-9551.
8. Barbucenu, S. F.; Bancescu, G.; Cretu, O. D.; Draghici, C.; Bancescu, A.; Radu-Popescu, M. Rev. Chem. (Bu- curesti) 2010 , 61 , 140-145.
9. Narwade, S. K.; Halnor, V. B.; Dalvi, N. R.; Gill, C. H.; Karale, B. K. Ind. J. Chem . 2006 , 45B , 2776-2780.
10. Dobrota, C.; Paraschivescu, C. C.; Dumitru, I.; Matache, M.; Baciu, I.; Ruta, L. L. Tetrahedron Lett. 2009 , 50 , 1886-1888.
11. Misra, U.; Hitkari, A.; Saxena, A. K.; Gurtu, S.; Shanker, K. Eur. J. Med. Chem . 1996 , 31 , 629-634.
12. Amir, M.; Kumar, S. Acta Pharm . 2007 , 57 , 31-45.
13. Khan, M. S. Y.; Akhtar, M. Ind. J. Chem . 2003 , 42B , 900-904.
14. Sharba, A.; Al-Bayati, R.; Aouad, M.; Rezki, N. Molecules 2005 , 10 , 1161-1168.
15. Bhat, M. A.; Siddiqui, N.; Khan, S. A. Acta Pol. Pharm. Drug Res . 2008 , 65 , 235-239.
16. Fuloria, N. K.; Singh, V.; Shaharyar, M.; Ali, M. Molecules 2009 , 14 , 1898-1903.
17. Deasi, N. C.; Dodiya, A. M. Arab. J. Chem . 2016 , 9 , S379-S387.
18. Aanandhi, M. V.; Mansoori, M. H.; Shanmugapriya, S.; George, S.; Shanmugasundaram, P. Res. J. Pharm. Biol. Chem. Sci . 2010 , 1 , 1083-1090.
19. Chawla, R.; Arora, A.; Parameswaran, M. K.; Chandersharma, P.; Michael, S., Ravi, T. K. Acta Pol. Pharm. Drug Res . 2010 , 67 , 247-253.
20. Jedlovska, E.; Lesko, J. Synth. Commun . 1994 , 24 , 1879-1885.
21. Cin, G. T.; Verep, G.; Topel, S. D.; Ciger, V. Chem. Heterocyclic Comp . 2013 , 49 , 1061-1067.
22. Pudota, P. T.; Purohit, R. S. M.; Pujar, G. V. J. App. Chem. Res . 2013 , 7 , 7-18.
23. Dabholkar, V. V.; Gavande, R. P. Rasayan J. Chem . 2010 , 3 , 655-659.
24. Kumar, A.; Makrandi, J. K. Green Chem. Lett. Rev. 2011 , 4 , 87-89.
25. Cohen, M. L. Science 1992 , 257 , 1050-1055.
26. Giamarellou, H. Expert Rev. Anti. Infect. Ther . 2006 , 4 , 601-618.
27. Behalo, M. S. RSC Adv . 2016 , 6 , 103132-103136.
28. Sarkanj, B.; Molnar, M.; Cacic, M.; Gille, L. Food Chem . 2013 , 139 , 488-495.
29. Molnar, M.; Sarkanj, B.; Cacic, M.; Gille, L.; Strelec, I . Der Pharma Chem . 2016 , 6 , 313-320.
30. Eid, A. I.; Ragab, F. A.; El-Ansary, S. L.; El-Gazayerly, S. M.; Mourad, F. E. Arch. Pharm. (Wienheim) . 1994 , 327 , 211-213.
31. Prieto, P.; Pineda, M.; Aguilar, M. Anal. Biochem. 1999 , 269 , 337-341.
32. Cacic, M.; Pavic, V.; Molnar, M.; Sarkanj, B.; Has-Schon, E. Molecules 2014 , 19 , 1163-1177.
33. Chanda, A.; Roze, L. V.; Kang, S.; Artymovich, K. A.; Hicks, G. R.; Raikhel, N. V.; Calvo, A. M.; Linz, J. E. Proc. Natl. Acad. Sci . USA . 2009 , 106 , 19533-19538.
34. Kovac, T.; Kovac, M.; Strelec, I.; Nevistic, A.; Molnar, M. Arh. Hig. Rada Toksikol. 2017 , 68 , 9-15.
35. Molnar, M.; Pavic, V.; Sarkanj, B.; Cacic, M.; Vukovic, D.; Klenkar, J. Heterocyc. Commun . 2017 doi: 10.1515/hc- 2016-0078
36. Gu, W.; Wang, S. Eur. J. Med. Chem. 2010 , 45 , 4692-4696.