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Novel Synthesis Method of Pyrimidine and Pyrazole Derivatives
Corresponding Author(s) : B.E. Missaoui
Asian Journal of Chemistry,
Vol. 27 No. 2 (2015): Vol 27 Issue 2
Abstract
The purpose of this work is the development of a synthetic method that allows access to some heterocyclic compounds containing pyrimidine and pyrazole nuclei. The dehydroacetic acid has been extensively studied as a starting material for the synthesis of natural products that exhibit valuable pharmacological properties. In the first part, we have shown that the pyrimidines can be obtained by reacting dehydroacetic acid with nitrogen binucleophiles reagents. In the second part, we presented the reactivity of the previously synthesized derivatives towards hydrazine to yield derivatives involving pyrimidine and pyrazole motifs. All the synthesized products were subjected to IR, 1H NMR and mass spectra studies.
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References
R.E. Chipkin and J.T. Witkowshi, PCT Int. Appl. WO, 85,846 (1986).
K. Hirai and M. Tsutsuminchi, Jpn Kokai Tokyo Koho, JP 6157587 (1986).
G.P. McGlacken and I.J.S. Fairlamb, Nat. Prod. Rep., 22, 369 (2005); doi:10.1039/B416651P.
H.I. El-Subbagh, S.M. Abu-Zaid, M.A. Mahran, F.A. Badria and A.M. Al-Obaid, J. Med. Chem., 43, 2915 (2000); doi:10.1021/jm000038m.
W. Gauss, H. Herlinger, H. Thomas and M. Plempel, US Patent 3,609,166 (1971).
N.R. Person and C.M. Carson, P.C.T. Int. Appl. WO, 89,368 (1989).
J.V. Ran, D.S. Kushwaha and L. Mishra, Indian J. Chem., 28B, 242 (1989).
Y. Shiga, I. Okada, Y. Ikeda, E. Takizawa and T. Fukuchi, Pestic. Sci., 28, 313 (2003); doi:10.1584/jpestics.28.313.
A. Balbi, M. Anzaldi, M. Mazzei, M. Miele, M. Bertolotto, L. Ottonello and F. Dallegri, Bioorg. Med. Chem., 14, 5152 (2006); doi:10.1016/j.bmc.2006.04.007.
I. Brouet and H. Ohshima, Biochem. Biophys. Res. Commun., 206, 533 (1995); doi:10.1006/bbrc.1995.1076.
J.L. Arbiser, N. Klauber, R. Rohan, R. Van Leeuwen, M.T. Huang, C.C. Fisher, E. Flynn and H. Byers, Mol. Med., 4, 376 (1998).
A. Jacob, R. Wu, M. Zhou and P. Wang, PPAR Res., 89, 369 (2007).
R.A. Sharma, C.R. Ireson, R.D. Verschoyle, K.A. Hill, M.L. Williams, C. Leuratti, M.M. Manson, L.J. Marnett, W.P. Steward and A. Gescher, Clin. Cancer Res., 7, 1452 (2001).
M. Füllbeck, X. Huang, R. Dumdey, C. Frommel, W. Dubiel and R. Preissner, BMC Cancer, 5, 97 (2005); doi:10.1186/1471-2407-5-97.
D.R. Siwak, S. Shishodia, B.B. Aggarwal and R. Kurzrock, Cancer, 104, 879 (2005); doi:10.1002/cncr.21216.
D.J. Wustrow, T. Capiris, R. Rubin, J.A. Knobelsdorf, H. Akunne, M.D. Davis, R. MacKenzie, T.A. Pugsley, K.T. Zoski, T.G. Heffner and L.D. Wise, Bioorg. Med. Chem. Lett., 8, 2067 (1998); doi:10.1016/S0960-894X(98)00372-2.
T. Penning, J. Talley, S. Bertenshaw, J. Carter, P. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang and P.C. Isakson, J. Med. Chem., 40, 1347 (1997); doi:10.1021/jm960803q.
N. Terrett, A. Bell, D. Brown and P. Ellis, Bioorg. Med. Chem. Lett., 6, 1819 (1996); doi:10.1016/0960-894X(96)00323-X.
C.R. Prokopp, M.A. Rubin, P.D. Sauzem, A.H. de Souza, D.B. Berlese, R.V. Lourega, M.N. Muniz, H.G. Bonacorso, N. Zanatta, M.A.P. Martins and C.F. Mello, Braz. J. Med. Biol. Res., 39, 795 (2006); doi:10.1590/S0100-879X2006000600013.
W.W. Wardakhan and N.A.J. Louca, Chil. Chem. Soc., 52, 1145 (2007).