Synthesis and evaluation of some novel thiazoles and 1,3-thiazines as potentagents against the rabies virus
Synthesis and evaluation of some novel thiazoles and 1,3-thiazines as potentagents against the rabies virus
A series of novel thiazoles and 1,3-thiazine derivatives were synthesized in good yield via reaction of ethyl3-(1-(2-thiocarbamoylhydrazono)ethyl)-1,5-diphenyl-1H-pyrazole-4-carboxylate with hydrazonoyl halides and aryliden-emalononitriles, respectively. The structure of the newly synthesized products was elucidated via elemental analysis,spectral data, and alternative routes whenever possible. Moreover, the antiviral screening of the products was evaluatedand the results revealed that some of them have strong to moderate potency against the rabies virus compared with thereference drug.
___
- 1.Wunner, W. H.; Briggs, D. J.PLoS Negl Trop Dis.2010,3, e591.
- 2.Wilkinson, L.; Jackson, A. C.; Wunner, W. H., eds., Academic Press: New York, NY, USA, 2002, pp. 1-22.
- 3.Rupprecht, C. E.; Hanlon, C. A.; Hemachudha, T.Lancet Infect. Dis.2002,2, 327-343.
- 4.Willoughby, R. E.; Tieves, J. R.; Hoffman, K. S.; Ghanayem, G. M.; Amlie-Lefond, N. S.; Schwabe. C. M.; Chusid,M. J.; Rupprecht, M. J.; Survival, C. E.New Engl. J. Med.2005,352, 2508-2514.
- 5.Franka, R.; Rupprecht, C. E.Future Microbiol.2011,6, 1135-1140.
- 6.Muller, V.; Chavez, J. H.; Reginatto, F. H.; Zucolotto, S. M.; Niero, R.; Navarro, D.; Yunes, R. A.; Schenkel, E.P.; Barardi, C. R.; Zanetti, C. R.Phytother. Res.2007,21, 970-974.
- 7.Mansour, H. A.; Shoman, S. A.; Kdodier, M. H.Acta Biol. Hung.2011,62, 194-203.
- 8.Chavez, J. H.; Leal, P. C.; Yunes, R. A.; Nunes, R. J.; Barardi, C. R.; Pinto, A. R.; Simoes, C. M.; Zanetti, C. R.Vet. Microbiol.2006,116, 53-59.
- 9.Wiktor, T. J.; Clark, H. F.Infect. Immun.1972,6, 988-995.
- 10.Consales, C. A.; Mendonca, R. Z.; Gallina, N. M.; Pereira, C. A.J. Virol. Methods1990,27, 277-285.
- 11.Nogueira, Y. L.Rev. Inst. Adolfo Lutz1992,52, 9-16.
- 12.Nogueira, Y. L.; Amaral, C. A.Rev. Inst. Adolfo Lutz1992,52, 17-21.
- 13.Smee, D. F.; Morrison, A. C.; Barnard, D. L; Sidwell, R.W.J. Virol. Methods2002,106, 71-79.
- 14.Mosmann, T.J. Immunol. Methods1983,65, 55-63.
- 15.Takeuchi, H.; Baba, M.; Shigeta, S.J. Virol. Methods1991,33, 61-71.
- 16.Savi, L. A.; Leal, P. C.; Vieira, T. O.; Rosso, R.; Nunes, R. J.; Yunes, R. A.; Creczynski-Pasa, T. B.; Barardi, C.R.; Simoes, C. M.Arzneim. Forsch.2005,55, 66-75.
- 17.Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; De Clercq, E.J. Virol.Methods1988,20, 309-321.
- 18.Nakashima, H.; Pauwels, R.; Baba, M.; Schols, D.; Desmyter, J.; De Clercq, E.J. Virol. Methods1989,26, 319-329.
- 19.Kiyohara, H.; Ichino, C.; Kawamura, Y.; Nagai, T.; Sato, N.; Yamada, H.; Salama, M. M.; Abdel-Sattar, E.Phytomedicine2012,19, 11-14.
- 20.Gomha, S. M.; Salah, T. A.; Abdelhamid, A. O.Monatsh. Chem.2015,146, 149-158.
- 21.Gomha, S. M.; Ahmed, S. A.; Abdelhamid, A. O.Molecules2015,20, 1357-1376.
- 22.Gomha, S. M.; Abdel-Aziz, H. A.Bull. Korean Chem. Soc.2012,33, 2985-2990:
- 23.Gomha, S. M.; Khalil, K. D.Molecules2012,17, 9335-9347.
- 24.Karegoudar, P.; Karthikeyan, M. S.; Prasad, D. J.; Mahalinga, M.; Holla, B. S.; Kumari, N. S.Eur. J. Med. Chem.2008,43, 261- 267.
- 25.Cukurovali, A.; Yilmaz, I.; Gur, S.; Kazaz, C.Eur. J. Med. Chem.2006,41, 201-207.
- 26.Shih, M. H.; Ying, K. F.Bioorg. Med. Chem.2004,12, 4633-4643.
- 27.Shiradkar, M.; Kumar, G. V. S.; Dasari, V.; Tatikonda, S.; Akula, K. C.; Shah, R.Eur. J. Med. Chem.2007,42,807-816.
- 28.Gomha, S. M.; Badrey, M. G.J. Chem. Res.2013, 86-90.
- 29.Gomha, S. M.; Riyadh, S. M.; Abbas, I. M.; Bauomi, M. A.Heterocycles2013,87, 341-356.
- 30.Rathore, M. M. V.; Parhate, V.; Rajput, P. R.Int. J. Res. Pharm. Biomed. Sci.2013,4, 59-62.
- 31.Jupudi, S.; Talari, S.; Karunakaram, D.; Govindarajan, R.Int. J. Res. Pharm. Chem.2013,3, 213-220.
- 32.Ferreira, M.; Assunc~ao, L. S.; Filippin-Monteiro, F. B.; Creczynski-Pasa, T. B.; Sa, M. M.Eur. J. Med. Chem.2013,70, 411-418.
- 33.Wang, W.; Zhao, B.; Xu, C; Wu, W.Int. J. Org. Chem.2012,2, 117-120.
- 34.Ibrahim, M. K. A.; El-Ghandour, A. H. H.; Abou-hadeed, K.; Abdelha z, I. S. J.;Indian Chem. Soc.1992,69,378
- 35.El-Sherbeny, M. A.; El-Ashmawy, M. B.; El-Subbagh, H. I.; El-Emam, A. A.; Badria, F. A.Eur. J. Med. Chem.1995,30, 445{449.
- 36.El-Subbagh, H. I.; Abu-Zaid, S. M.; Mahran, M. A.; Badria, F. A.; El-Rahman, M. A.J. Med. Chem.2000,43,2915-2921.
- 37.Hufford, C. D.; Badria, F. A.; Abou-Karam, M.; Shier, W. T.; Rogers, R. D.J. Nat. Prod.1991,54, 1534-1552.
- 38.Shawali, A. S.; Osman, A.Bull. Chem. Soc. Jpn.1976,49, 321-324.
- 39.Shawali, A. S.; Osman, A.Tetrahedron1971,27, 2517-2528.
- 40.Abdelhamid, A. O.; El-Shiatey, F. H. H.Phosphorus, Sulfur, Silicon Related Elem.1988,39, 45-49.
- 41.Hassaneen, H. M.; Shawali, A. S.; Elwan,; N. M.; Abounada, N. M.Sulfur Lett.1992,13, 273-285.
- 42.Wolkoff, P.Can. J. Chem.1975,53, 1333-1335.
- 43.Simoes, C. M.; Amoros, M.; Girre, L.Phytother. Res.1999,13, 323-328.453