Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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QSAR Studies on the Inhibitory Activity of New Methoxyacrylate Analogues against Magnaporthe grisea (Rice Blast Disease)

  • Song, Young-Seob (Korea Research Institute of Chemical Technology, Department of Applied Biology & Chemistry, Chung-Nam National University) ;
  • Sung, Nack-Do (Department of Applied Biology & Chemistry, Chung-Nam National University) ;
  • Yu, Yong-Man (Department of Agricultural Biology, College of Agricultural & Life Science, Chung-Nam National University) ;
  • Kim, Bum-Tae (Korea Research Institute of Chemical Technology)
  • Published : 2004.10.20
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Abstract

We investigate a series of synthesized ${\beta}$-methoxyacrylate analogues for their 3D QSAR & HQSAR against Magnaporthe grisea (Rice Blast Disease). We perform the three-dimensional Quantitative Structure-Activity Relationship (3D-QSAR) studies, using the comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) procedure. In addition, we carry out a two-dimensional Quantitative Structure-Activity Relationship (2D-QSAR) study, using the Hologram QSAR (HQSAR). We perform these studies, using 53 compounds as a training set and 10 compounds as a test set. The predictive QSAR models have conventional $r^2$ values of 0.955 at CoMFA, 0.917 at CoMSIA, and 0.910 at HQSAR respectively; similarly, we obtain cross-validated coefficient $q^2$ values of 0.822 at CoMFA, 0.763 at CoMSIA, and 0.816 at HQSAR, respectively. From these studies, the CoMFA model performs better than the CoMSIA model.

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References

  1. Konradt, M.; Kappes, E. M.; Hiemer, M.; Peterson, H. H. GesundePflanzen 1996, 48(4), 126.
  2. Dave, W. B.; John, M. C.; Jeremy, R. G. Pest Manag Sci. 2002, 58,649. https://doi.org/10.1002/ps.520
  3. Tamura, H.; Mizutani, A. Nippon Noyaku Gakkaishi 1999, 24(2), 189.
  4. Wittman, M. D.; Kallmerten, J. J. Org. Chem. 1987, 52(19), 4303. https://doi.org/10.1021/jo00228a028
  5. Martin, B. J.; Clough, J. M.; Pattenden, G.; Waldron, I. R.Tetrahedron Letters 1993, 34(32), 5151. https://doi.org/10.1016/S0040-4039(00)60700-1
  6. Crammer, R. D., III; Patterson, D. E.; Bunce, J. D. J. Am. Chem.Soc. 1988, 110, 5959. https://doi.org/10.1021/ja00226a005
  7. Gokhale, V. M.; Kulkarni, V. M. J. Med. Chem. 1999, 42, 5348. https://doi.org/10.1021/jm9806852
  8. Klebe, G.; Abraham, U.; Mietzner, T. J. Med. Chem. 1994, 37,4130. https://doi.org/10.1021/jm00050a010
  9. Borosy, A. P.; Keseru, K.; Penzes, I.; Matyus, P. J. MolecularStructure (Theochem) 2000, 503, 113. https://doi.org/10.1016/S0166-1280(99)00367-X
  10. Rambard, M.; Bakasse, H.; Duguay, G.; Villieras, J. Synthesis1988, 564.
  11. Yamada, K.; Kato, M.; Hirata, Y. Tetrahedron Lett. 1973, 14,2745. https://doi.org/10.1016/S0040-4039(01)96128-3
  12. Herkes, F. E.; Burton, D. J. J. Org. Chem. 1967, 32, 1311. https://doi.org/10.1021/jo01280a007
  13. Nemeth, G.; Rakoczya, E.; Simiga, G. J. Fluorine Chem. 1996,76, 91. https://doi.org/10.1016/0022-1139(95)03338-6
  14. SYBYL 6.9; Tripos Inc.: USA, 0000.
  15. Gasteteiger, J.; Marsili, M. Tetrahedron 1980, 36, 3219. https://doi.org/10.1016/0040-4020(80)80168-2
  16. Purushottamachar, P.; Kulkarni, V. M. Biooragnic & MedicinalChemistry 2003, 11, 3487. https://doi.org/10.1016/S0968-0896(03)00305-5
  17. Roh, E. J.; Kim, D.; Choi, J. Y.; Lee, B. S.; Lee, C. O.; Song, C. E.Bioorganic & Medicinal Chemistry 2002, 10, 3135. https://doi.org/10.1016/S0968-0896(02)00217-1
  18. Hou, T.; Li, Y.; Liao, N.; Xu, X. J. Mol. Model 2000, 6, 438. https://doi.org/10.1007/s0089400060438
  19. Islam, M. N.; Song, Y.; Iskander, M. N. J. Molecular Graphicsand Modeling 2003, 21, 263. https://doi.org/10.1016/S1093-3263(02)00162-6
  20. Choo, H. P.; Choi, S.; Ryu, C. K.; Kim, H. J.; Lee, I. Y.; Pae, A.N.; Koh, H. Y. Biooragnic & Medicinal Chemistry 2003, 11, 2019. https://doi.org/10.1016/S0968-0896(03)00045-2
  21. Xu, M.; Zhang, A.; Han, S.; Wang, L. Chemosphere 2002, 48,707. https://doi.org/10.1016/S0045-6535(02)00165-0
  22. Kim, B. T.; Park, N. K.; Kim, J. C.; Choi, K. J.; Park, C. S. U.S. Pat. 6552080 2003/04/22

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