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Synthesis and Evaluation of Novel Xanthone Derivatives as Potent Dipeptidyl Peptidase-4 Inhibitors
Corresponding Author(s) : Qingjie Zhao
Asian Journal of Chemistry,
Vol. 27 No. 6 (2015): Vol 27 Issue 6
Abstract
Two series of xanthone derivatives have been designed, synthesized and evaluated as potent dipeptidyl peptidase-4 inhibitors and among them seven compounds were firstly reported. Most of the inhibitors showed moderate inhibitory activities aganist dipeptidyl peptidase-4 and compounds 2a, 2c, 2d, 2f and 2g exhibited potent activities against dipeptidyl peptidase-4 compared with the positive control diprotin A.
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- M. Talaei, M. Sadeghi, T. Marshall, G.N. Thomas, R. Iranipour, N. Nazarat and N. Sarrafzadegan, Diabetes Metab., 39, 424 (2013); doi:10.1016/j.diabet.2013.04.001.
- M.A. Nauck, O. Baranov, R.A. Ritzel and J.J. Meier, Diabetologia, 56, 1878 (2013); doi:10.1007/s00125-013-2953-6.
- R.E. Pratley and A. Salsali, Curr. Med. Res. Opin., 23, 919 (2007); doi:10.1185/030079906X162746.
- X. Ji, M. Su, J. Wang, G. Deng, S. Deng, Z. Li, C. Tang, J. Li, J. Li, L. Zhao, H. Jiang and H. Liu, Eur. J. Med. Chem., 75, 111 (2014); doi:10.1016/j.ejmech.2014.01.021.
- J. Feng, Z. Zhang, M.B. Wallace, J.A. Stafford, S.W. Kaldor, D.B. Kassel, M. Navre, L. Shi, R.J. Skene, T. Asakawa, K. Takeuchi, R. Xu, D.R. Webb and S.L. Gwaltney, J. Med. Chem., 50, 2297 (2007); doi:10.1021/jm070104l.
- H. Hu, H. Liao, J. Zhang, W. Wu, J. Yan, Y. Yan, Q. Zhao, Y. Zou, X. Chai, S. Yu and Q. Wu, Bioorg. Med. Chem. Lett., 20, 3094 (2010); doi:10.1016/j.bmcl.2010.03.101.
- H.G. Hu, M.J. Wang, Q.J. Zhao, H.L. Liao, L.Z. Cai, Y. Song, J. Zhang, S.C. Yu, W.S. Chen, C.M. Liu and Q.Y. Wu, Chem. Nat. Comp., 43, 663 (2007); doi:10.1007/s10600-007-0223-x.
- H.G. Hu, M.J. Wang, Q.J. Zhao, S.C. Yu, C.M. Liu and Q.Y. Wu, Chin. Chem. Lett., 18, 1323 (2007); doi:10.1016/j.cclet.2007.09.011.
- P.E. Eaton, G.R. Carlson and J.T.J. Lee, Org. Chem., 38, 4071 (1973); doi:10.1021/jo00987a028.
- N.R. Ayyangar, K.C. Brahme, U.R. Kalkote and K.V. Srinivasan, Synthesis, 938 (1984); doi:10.1055/s-1984-31027.
- Representative analytical data for compound 2a, yield 72 %, 1HNMR (300 MHz, DMSO-d6, TMS): δ 10.41 (1 H, br, NH), 8.25 (1 H, s, Ar), 7,96 (1 H, br, Ar), 7.48 (1 H, d, Ar), 6.66 (1 H, s, Ar), 6.49 (1 H, s, Ar), 3.88 (3 H, s, OCH3), 3.83 (3 H, m, OCH3), 3.83 (2 H, br, CH2), 2.88-2.32 (6 H, m, CH2), 1.51-1.37 (6 H, m, CH2). ESI-MS, m/z: Calcd. 410.2, Found, 411.1 [M+H]+.
References
M. Talaei, M. Sadeghi, T. Marshall, G.N. Thomas, R. Iranipour, N. Nazarat and N. Sarrafzadegan, Diabetes Metab., 39, 424 (2013); doi:10.1016/j.diabet.2013.04.001.
M.A. Nauck, O. Baranov, R.A. Ritzel and J.J. Meier, Diabetologia, 56, 1878 (2013); doi:10.1007/s00125-013-2953-6.
R.E. Pratley and A. Salsali, Curr. Med. Res. Opin., 23, 919 (2007); doi:10.1185/030079906X162746.
X. Ji, M. Su, J. Wang, G. Deng, S. Deng, Z. Li, C. Tang, J. Li, J. Li, L. Zhao, H. Jiang and H. Liu, Eur. J. Med. Chem., 75, 111 (2014); doi:10.1016/j.ejmech.2014.01.021.
J. Feng, Z. Zhang, M.B. Wallace, J.A. Stafford, S.W. Kaldor, D.B. Kassel, M. Navre, L. Shi, R.J. Skene, T. Asakawa, K. Takeuchi, R. Xu, D.R. Webb and S.L. Gwaltney, J. Med. Chem., 50, 2297 (2007); doi:10.1021/jm070104l.
H. Hu, H. Liao, J. Zhang, W. Wu, J. Yan, Y. Yan, Q. Zhao, Y. Zou, X. Chai, S. Yu and Q. Wu, Bioorg. Med. Chem. Lett., 20, 3094 (2010); doi:10.1016/j.bmcl.2010.03.101.
H.G. Hu, M.J. Wang, Q.J. Zhao, H.L. Liao, L.Z. Cai, Y. Song, J. Zhang, S.C. Yu, W.S. Chen, C.M. Liu and Q.Y. Wu, Chem. Nat. Comp., 43, 663 (2007); doi:10.1007/s10600-007-0223-x.
H.G. Hu, M.J. Wang, Q.J. Zhao, S.C. Yu, C.M. Liu and Q.Y. Wu, Chin. Chem. Lett., 18, 1323 (2007); doi:10.1016/j.cclet.2007.09.011.
P.E. Eaton, G.R. Carlson and J.T.J. Lee, Org. Chem., 38, 4071 (1973); doi:10.1021/jo00987a028.
N.R. Ayyangar, K.C. Brahme, U.R. Kalkote and K.V. Srinivasan, Synthesis, 938 (1984); doi:10.1055/s-1984-31027.
Representative analytical data for compound 2a, yield 72 %, 1HNMR (300 MHz, DMSO-d6, TMS): δ 10.41 (1 H, br, NH), 8.25 (1 H, s, Ar), 7,96 (1 H, br, Ar), 7.48 (1 H, d, Ar), 6.66 (1 H, s, Ar), 6.49 (1 H, s, Ar), 3.88 (3 H, s, OCH3), 3.83 (3 H, m, OCH3), 3.83 (2 H, br, CH2), 2.88-2.32 (6 H, m, CH2), 1.51-1.37 (6 H, m, CH2). ESI-MS, m/z: Calcd. 410.2, Found, 411.1 [M+H]+.