Synthesis, characterization and antifungal testing of 3,4-dihydropyrimidin-2(1H)-(thio)ones containing boronic acids and boronate esters

Central European Journal of Chemistry - Tập 6 - Trang 562-568 - 2008
Dominique R. Duguay1, Matthew T. Zamora1, Johanna M. Blacquiere1, Francis E. Appoh1, Christopher M. Vogels1, Susan L. Wheaton1, Felix J. Baerlocher2, Andreas Decken3, Stephen A. Westcott1
1Department of Chemistry, Mount Allison University, Sackville, Canada
2Department of Biology, Mount Allison University, Sackville, Canada
3Department of Chemistry, University of New Brunswick, Fredericton, Canada

Tóm tắt

The addition of formylphenylboronic acid derivatives to thiourea and ethyl acetoacetate proceeds in the presence of an additional Lewis acid catalyst to give the corresponding 3,4-dihydropyrimidin-2(1H)-(thio)ones (Biginelli products) in moderate yield. Compounds were tested for antifungal activity against pure cultures of Aspergillus niger, Aspergillus flavus, Candida albicans and Saccharomyces cerevisiae but, unfortunately, none showed any appreciable activity.

Tài liệu tham khảo

P. Biginelli, Gazz. Chim. Ital. 23, 360 (1893) P. Wipf, A. Cunningham, Tetrahedron Lett. 36, 7819 (1995) G. Sabitha, G.S.K.K. Reddy, Ch.S. Reddy, J.S. Yadav, SynLett 858 (2003) N.-Y. Fu, Y.-F. Yuan, Z. Cao, S.-W. Wang, J.-T. Wang, C. Peppe, Tetrahedron 58, 4801 (2002) I. Cepanec, M. Litvic, A. Bartolincic, M. Lovric, Tetrahedron 61, 4275 (2005) C. Liu, J. Wang, Y. Li, J. Mol. Catal. A: Chem. 258, 367 (2006) D. Russowsky et al., Bioorg. Chem. 34, 173 (2006) G.C. Rovnyak et al., J. Med. Chem. 38, 119 (1995) T.U. Mayer et al., Science 286, 971 (1999) C.O. Kappe, Eur. J. Med. Chem. 35, 1043 (2000) S.J. Vaghasia, V.H. Shah, J. Serb. Chem. Soc. 72, 109 (2007) A.K. Chhillar et al., Bioorg. Med. Chem. 14, 973 (2006) P. Sharma, N. Rane, V.K. Gurram, Bioorg. Med. Chem. Lett. 14, 4185 (2004) W. Yang, X. Gao, B. Wang, Med. Res. Rev. 23, 346 (2003) F.L. Rock et al., Science 316, 1759 (2007) C.M. Vogels et al., Can. J. Chem. 79, 1115 (2001) SAINT 6.02, Bruker AXS, Inc., Madison, Wisconsin, USA. (1997-1999) G.M. Sheldrick, SADABS, Bruker AXS, Inc. ( Madison, Wisconsin, USA, 1999) G.M. Sheldrick, SHELXTL 5.1, Bruker AXS, Inc. ( Madison, Wisconsin, USA, 1997) H. Nöth and B. Wrackmeyer, In Nuclear magnetic resonance spectroscopy of boron compounds (Springer-Verlag, Berlin, 1978) H. Höpfl, J. Organomet. Chem. 581, 129 (1999) J.C. Barrow et al., J. Med. Chem. 43, 2703 (2000) A. Dondoni, A. Massi, E. Minghini, S. Sabbatini, V. Bertolasi, J. Org. Chem. 68, 6172 (2003) C.O. Kappe, W.M.F. Fabian, M.A. Semones, Tetrahedron 53, 2803 (1997) V. Martichonok, J.B. Jones, J. Am. Chem. Soc. 118, 950 (1996) R.B. Coapes et al., J. Chem. Soc., Dalton Trans. 1201 (2001) C. Zheng, B.F. Spielvogel, R.Y. Smith, N.S. Hosmane, Z. Kristallogr. NCS 216, 341 (2001) S. Hawkswood, D.W. Stephan, Dalton Trans. 2182 (2005) A. Goswami, C.-J. Maier, H. Pritzkow, W. Siebert, Eur. J. Inorg. Chem. 2635 (2004) F.J. Baerlocher, M.O. Baerlocher, C.L. Chaulk, R.F. Langler, S.L. MacQuarrie, Aust. J. Chem. 53, 399 (2000) A.M. Irving et al., New J. Chem. 27, 1419 (2003)