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Design, Synthesis and Characterization of Pyrimidine based Thiazolidinedione Derivatives
Corresponding Author(s) : Anup Barde
Asian Journal of Chemistry,
Vol. 32 No. 5 (2020): Vol 32 Issue 5
Abstract
Novel thiazolidine-2,4-dione (TZD) based pyrimidine derivatives have been synthesized by Knoevenagel condensation reaction between thiazolidine-2,4-dione and amino pyrimidinyl aliphatic aldehydes followed by heterogeneous metal reduction. Synthetic strategy involved nucleophillic substitution of hydroxyl protected six membered aliphatic chain on 4,6-dichloropyrimidine followed by Suzuki coupling. This approach is regioselective, efficient and versatile for synthesis of such analogs.
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- Z.S. Safi, Arab. J. Chem., 9, 616 (2016); https://doi.org/10.1016/j.arabjc.2015.03.016
- S.P. Singh, S.S. Parmar, K. Raman and V.I. Stenberg, Chem. Rev., 81, 175 (1981); https://doi.org/10.1021/cr00042a003
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- D. da Silva Pinheiro, E.N. dos Santos Junior, G. Consolini, M.J. Aguiar, R.R. de Oliveira Silva, R. de Oliveira Vieira and M.S.A. Palma, MOJ Biorg. Org. Chem., 1, 122 (2017); https://doi.org/10.15406/mojboc.2017.01.00022
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References
Z.S. Safi, Arab. J. Chem., 9, 616 (2016); https://doi.org/10.1016/j.arabjc.2015.03.016
S.P. Singh, S.S. Parmar, K. Raman and V.I. Stenberg, Chem. Rev., 81, 175 (1981); https://doi.org/10.1021/cr00042a003
M.T. Omar and M.A. Kasem, J. Heterocycl. Chem., 18, 1413 (1981); https://doi.org/10.1002/jhet.5570180727
B.C. Sekhar, J. Heterocycl. Chem., 41, 807 (2004); https://doi.org/10.1002/jhet.5570410601
H. Yanagisawa, M. Takamura, E. Yamada, S. Fujita, T. Fujiwara, M. Yachi, A. Isobe and Y. Hagisawa, Bioorg. Med. Chem. Lett., 10, 373 (2000); https://doi.org/10.1016/S0960-894X(00)00003-2
D.A. Heerding, L.T. Christmann, T.J. Clark, S.F. Rittenhouse, D.J. Holmes, D.T. Takata and J.W. Venslavsky, Bioorg. Med. Chem. Lett., 13, 3771 (2003); https://doi.org/10.1016/j.bmcl.2003.07.010
B.C. Cantello, M.A. Cawthorne, D. Haigh, R.M. Hindley, S.A. Smith and P.L. Thurlby, Bioorg. Med. Chem. Lett., 4, 1181 (1994); https://doi.org/10.1016/S0960-894X(01)80325-5
M.C. Wiesenberg, M. Misbach, W. Pigat and C. Carlberg, Mol. Pharmacol., 53, 1131 (1998).
N. Chadha, M.S. Bahia, M. Kaur and O. Silakari, Bioorg. Med. Chem., 23, 2953 (2015); https://doi.org/10.1016/j.bmc.2015.03.071
V.S. Jain, D.K. Vora and C.S. Ramaa, Bioorg. Med. Chem., 21, 1599 (2013); https://doi.org/10.1016/j.bmc.2013.01.029
H. Kumar, A. Deep and R.K. Marwaha, Mini-Rev. Med. Chem., 19, 1474 (2019): https://doi.org/10.2174/1389557519666190513093618
T.-K. Yeh, C.-C. Kuo, Y.-Z. Lee, Y.-Y. Ke, K.-F. Chu, H.-Y. Hsu, H.-Y. Chang, Y.-W. Liu, J.-S. Song, C.-W. Yang, L.-M. Lin, M. Sun, S.-H. Wu, P.-C. Kuo, C. Shih, C.-T. Chen, L.K. Tsou and S.-J. Lee, J. Med. Chem., 60, 5599 (2017); https://doi.org/10.1021/acs.jmedchem.7b00282
Sucheta, S. Tahlan and P.K. Verma, Chem. Central J., 12, 129 (2018); https://doi.org/10.1186/s13065-018-0496-0
D. da Silva Pinheiro, E.N. dos Santos Junior, G. Consolini, M.J. Aguiar, R.R. de Oliveira Silva, R. de Oliveira Vieira and M.S.A. Palma, MOJ Biorg. Org. Chem., 1, 122 (2017); https://doi.org/10.15406/mojboc.2017.01.00022
S. Allen, B.N. Newhouse, A.S. Anderson, B. Fauber, A. Allen, D. Chantry, C. Eberhardt, J. Odingo and L.E. Burgess, Bioorg. Med. Chem. Lett., 14, 1619 (2004); https://doi.org/10.1016/j.bmcl.2004.01.072
Y. Momose, T. Maekawa, T. Yamano, M. Kawada, H. Odaka, H. Ikeda and T. Sohda, J. Med. Chem., 45, 1518 (2002); https://doi.org/10.1021/jm010490l
G. Mcgeoch, C. Mckeen, A. Osnowski and J. Wilson, WO Patent 132577A1 (2005).
G. Mcgeoch, M. Catherine, O. Andrew and W. Jennifer, WO Patent 132577 (2015).
T. Hisao, N. Yoshisuke and F. Daikichi, US Patent 6664281B (2003).
E.J. Corey and A. Venkateswarlu, J. Am. Chem. Soc., 94, 6190 (1972); https://doi.org/10.1021/ja00772a043
J.R. Parikh and W.E. Doering, J. Am. Chem. Soc., 89, 5505 (1967); https://doi.org/10.1021/ja00997a067
D.B. Dess and J.C. Martin, J. Org. Chem., 48, 4155 (1983); https://doi.org/10.1021/jo00170a070
J. Fischer, T. Fodor and E. Petenyi, WO Patent 058827A1 (2005).