Abstract
Four novel thiourea derivatives containing a thiazole moiety were synthesized and characterized by IR, 1H and 13C NMR, mass spectrometry and elemental analysis. The crystal structure of 1a was determined from single crystal X-ray diffraction data. It crystallizes in monoclinic space group P21/n with unit cell dimensions a = 11.7752(6) Å, b= 3.8677(2) Å, c= 27.4126(13) Å and β = 92.734(5) Å. There is a strong intramolecular hydrogen bond of the type N-H⋯O, with H⋯O distance of 2.5869(19) Å. The mass fragmentation pattern has also been discussed. The antifungal activity of the synthesized compounds was studied by broth micro-dilution method and poisoned food technique. The compounds 1b and 1c possessed a broad spectrum of antifungal activity. 
[1] T. Eicher, S. Hauptmann, The Chemistry of Heterocycles, 2nd edition (Wiley-VCH, Weinheim, 2003) 10.1002/352760183XSearch in Google Scholar
[2] N.G. Pershin, L.I. Sherbakova, T.N. Zykova, V.N. Sakolova, World Rev. Pest. Contr. 35, 466 (1972) Search in Google Scholar
[3] G. Regnier, L. Canevar, R.J. Le, J.C. Douarec, S. Halstop, J. Daussy, J. Med. Chem. 15, 295 (1972) http://dx.doi.org/10.1021/jm00273a60010.1021/jm00273a600Search in Google Scholar PubMed
[4] C.A. Winter, E.A.R. Fisley, G.W. Nuss, Proc. Soc. Exp. Biol. Med. 111, 544 (1962) 10.3181/00379727-111-27849Search in Google Scholar PubMed
[5] K. Suguira, A.F. Schmid, M.M. Schmid, F.G. Brown, Cancer Chemother. Rep. 3, 231 (1973) Search in Google Scholar
[6] M.M. Mojtahedi, M.R. Saidi, J.S. Shirzi, M. Bolourtchian, Syn. Commun. 32, 851 (2002) http://dx.doi.org/10.1081/SCC-12000269310.1081/SCC-120002693Search in Google Scholar
[7] E. Maquoi et al., Clin. Cancer Res. 10, 4038 (2004) http://dx.doi.org/10.1158/1078-0432.CCR-04-012510.1158/1078-0432.CCR-04-0125Search in Google Scholar PubMed
[8] R.S. Zeng, J.P. Zou, S.J. Zhi, J. Chen, Q. Shen, Org. Lett. 61, 1657 (2003) http://dx.doi.org/10.1021/ol030024l10.1021/ol030024lSearch in Google Scholar PubMed
[9] M. D’hooghe, A. Waterinckx, N. De Kimpe, J. Org. Chem. 70, 227 (2005) http://dx.doi.org/10.1021/jo048486f10.1021/jo048486fSearch in Google Scholar PubMed
[10] R. Lakhan, B.J. Ral, J. Chem. Eng. Data 31, 501 (1986) http://dx.doi.org/10.1021/je00046a03510.1021/je00046a035Search in Google Scholar
[11] J. Lee et al., J. Med. Chem. 46, 3116 (2003) http://dx.doi.org/10.1021/jm030089u10.1021/jm030089uSearch in Google Scholar PubMed
[12] L. Nie et al., J. Org. Chem. 69, 6449 (2004) http://dx.doi.org/10.1021/jo049088f10.1021/jo049088fSearch in Google Scholar PubMed
[13] H. Park et al., Bioorg. Med. Chem. Lett. 14, 787 (2004) http://dx.doi.org/10.1016/j.bmcl.2003.11.01910.1016/j.bmcl.2003.11.019Search in Google Scholar
[14] S. Saeed, M.H. Bhatti, U. Yunus, P.G. Jones, Acta Crystallogr. E64, o1566 (2008) 10.1107/S1600536808022095Search in Google Scholar
[15] C.-L. Gu, L. Liu, J.-L. Zhao, D. Wang, Y.-J. Chen, Tetrahedron 18, 455 (2007) http://dx.doi.org/10.1016/j.tetasy.2007.02.01610.1016/j.tetasy.2007.02.016Search in Google Scholar
[16] Y. Xu, W. Hua, X. Liu, D. Zhu, Chinese J. Org. Chem. 24, 1217 (2004) Search in Google Scholar
[17] P.A. Yonova, G.M. Stoilkova, J. Plant Growth Regul. 23, 280 (2005) 10.1007/s00344-003-0054-3Search in Google Scholar
[18] S. Saeed, N. Rashid, R. Hussain, P.G. Jones, Acta Crystallogr. E65, o2106 (2009) 10.1107/S1600536809030803Search in Google Scholar
[19] S. Saeed, N. Rahid, A. Tahir, P.G. Jones, Acta Crystallogr. E65, o1870 (2009) 10.1107/S1600536809025884Search in Google Scholar
[20] S. Saeed, N. Rashid, R. Hussain, P.G. Jones, Acta Crystallogr. E65, o2568 (2009) 10.1107/S1600536809031304Search in Google Scholar
[21] T.B. Wei, J.C. Chen, X.C. Wang, Synth. Commun. 26, 1147 (1996) http://dx.doi.org/10.1080/0039791960800350710.1080/00397919608003507Search in Google Scholar
[22] V.O. Illi, Tetrahedron Lett. 20, 2431 (1979) http://dx.doi.org/10.1016/S0040-4039(01)86311-510.1016/S0040-4039(01)86311-5Search in Google Scholar
[23] D.S. Mansuroglu, H. Arslan, D.V. Derveer, G. Binzet, Phosphorus, Sulfur, and Silicon 184, 3221 (2009) http://dx.doi.org/10.1080/1042650090297974310.1080/10426500902979743Search in Google Scholar
[24] H. Arslan, D.S. Mansuroglu, D.V. Derveer, G. Binzet, Spectrochim. Acta, Part A 72, 561 (2009) http://dx.doi.org/10.1016/j.saa.2008.10.04910.1016/j.saa.2008.10.049Search in Google Scholar PubMed
[25] Z.-M. Jin, W. Zhao, Z. Jin, Powder Diff. 12, 47 (1997) 10.1017/S0885715600009428Search in Google Scholar
[26] Y.Q. Zhang, D.C. Zhang, Y. Cao, B. Zao, Acta Crystallogr. C 52, 1716 (1996) http://dx.doi.org/10.1107/S010827019600104710.1107/S0108270196001047Search in Google Scholar
[27] F.H. Allen, Acta Crystallogr. B 58, 380 (2002) http://dx.doi.org/10.1107/S010876810200389010.1107/S0108768102003890Search in Google Scholar PubMed
[28] G. Binzet, H. Arslan, U. Florke, N. Kulcu, N. Duran, J. Cood. Chem. 59, 1395 (2006) http://dx.doi.org/10.1080/0095897050051263310.1080/00958970500512633Search in Google Scholar
[29] M.F. Emen, H. Arslan, N. Kulcu, U. Florke, N. Duran, Pol. J. Chem. 79, 1615 (2005) Search in Google Scholar
[30] H. Arslan, U. Florke, N. Kulcu, J. Chem. Crystallogr. 33, 919 (2003) http://dx.doi.org/10.1023/A:102742981498910.1023/A:1027429814989Search in Google Scholar
[31] H. Arslan, N. Duran, G. Borekci, C.K. Ozer, C. Akbay, Molecules 14, 519 (2009) http://dx.doi.org/10.3390/molecules1401051910.3390/molecules14010519Search in Google Scholar PubMed PubMed Central
[32] G.M. Sheldrick, Acta Cryst. A64, 112 (2008) 10.1107/S0108767307043930Search in Google Scholar PubMed
[33] National Committee for Clinical Laboratory Standards, M7-A4 (NCCLS, Viallanova, PA, USA, 1997) Search in Google Scholar
[34] National Committee for Clinical Laboratory Standards, M27-A2 (NCCLS, Wayne, PA, USA, 2002) Search in Google Scholar
[35] H.L. Barnett, Illustrated genera of imperfect fungi, 2nd edition (Burgess Publ. Co., London, 1960) 225 Search in Google Scholar
[36] J.P. Melone, A.E. Maskett, Seed-borne fungi, Proc. Int. Seed Test Assoc. 29, 179 (1964) Search in Google Scholar
[37] D.D. Dhingra, J.B. Sinclair, Basic Plant Pathology Methods (CBS Publ. & Distr, New Delhi, 1993) Search in Google Scholar
[38] R.G.D. Steel, J.H. Torrie, Principles and procedures of Statistics, 2nd edition (McGraw Book Co., New York, 1990) Search in Google Scholar
© 2010 Versita Warsaw
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.
