Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Comparative Molecular Field Analyses (CoMFA) Models and Their Selectivity for the Herbicidal Activities of New Novel 2-(4-chloro-5-(2-chloroallyloxy)-2-fluorophenyl)-3-thioalkoxy-2,3,4,5,6,7-hexahydroisoindol-1-one Derivatives

새로운 2-(4-chloro-5-(2-chloroallyloxy)-2-fluorophenyl)-3-thioalkoxy-2,3,4,5,6,7-hexahydroisoindol-1-one 유도체들의 제초활성에 관한 비교 분자장 분석 모델과 선택성

  • Sung, Nack-Do (Division of Applied Biologies and Chemistry, College of Agriculture and Life Science, Chungnam National University) ;
  • Song, Jong-Hwan (Cytosine Laboratory, Korea Research Institute of Chemical Technology) ;
  • Kang, Eun-Kyu (Division of Applied Biologies and Chemistry, College of Agriculture and Life Science, Chungnam National University) ;
  • Jung, Hoon-Sung (Division of Applied Biologies and Chemistry, College of Agriculture and Life Science, Chungnam National University)
  • 성낙도 (충남대학교 농업생명과학대학 응용생물화학부) ;
  • 송종환 (한국화학연구원 세포화학연구팀) ;
  • 강은규 (충남대학교 농업생명과학대학 응용생물화학부) ;
  • 정훈성 (충남대학교 농업생명과학대학 응용생물화학부)
  • Published : 2005.12.31
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Abstract

The comparative molecular field analyses (CoMFA) models for the herbicidal activities against barnyardgrass (Echinochloa crus-galli) and rice plant (Orysa sativa L.) by the substituent (R) on the hexahydroisoindol-1-one ring in a series of new 2-(4-chloro-5-(2-chloroallyloxy)-2-fluorophenyl)-3-thioalkoxy-2,3,4,5,6,7-hexahydroisoindol-1-one derivatives were conducted and discussed for selectivity between both plants. The statistical results of the two best models (B2 & R7) showed the best predictability for the herbicidal activities based on the cross-validated value $q_2(r^2cv.=0.529{\sim}0.755)$ and none cross-validated value $({r^2}_{ncv.}=0.937{\sim}0.945)$, respectively. Based on the findings, the predictability and fitness of the model (B2) for barnyard grass was better than that of the model (R7) for rice plant. From the two models and contour maps, it is revealed that the novel selective character for herbicidal activity between the two plants depend on the electrostatic field and steric field for the substituent of ortho-positions on the S-phenyl group as R-substituent in hexahydroisoindol-1-one ring.

새로운 2-(4-chloro-5-(2-chloroallyloxy)-2-fluorophenyl)-3-thioalkoxy-2,3,4,5,6,7-hexahydroisoindol-1-one 유도체의 hexahydroisoindol-1-one 고리상 R-치환기 변화에 따른 논피(Echinochloa crusgalli)와 벼(Orysa sativa L.)에 대한 제초활성에 관한 비교 분자장 분석(CoMFA) 모델을 유도하고 두 초종에 대한 선택성에 관하여 논의하였다. 가장 양호한 두 모델(B2 및 R7)의 통계결과는 교차 확인값 $q^2({r^2}_{cv.}=0.529{\sim}0.755)$과 비교차 확인값$({r^2}_{ncv.}=0.937{\sim}0.945)$에 기초하여 가장 양호한 예측성을 보였다. 그리고 논피에 대한 모델(B2)의 예측성과 적합성이 벼에 대한 모델(R7) 보다도 통계적으로 양호하였다. 또한, 두 모델과 기여도로부터 정전기장과 hexahydroisoindol-1-one 고리상 S-phenyl 기의 ortho-위치에 있는 입체장이 두 초종 간 선택적인 제초활성에 미치는 중요한 요소이었다.

Keywords

References

  1. Copping, L. G. and Hewitt, H. G. (1998) In Chemistry and Mode of Action of Crop Protection Agents. Chap. 2., The Royal Society of Chemistry. London
  2. Boger, P and Wakabayashi, K. (1999) In Peroxidizing Herbicides, Springer-Verlag Berline Heidelberg. Germany
  3. Fujita, T. (2002) In Agrochemical Discovery, Insect, Weed, and Fungal control: Similarities in bioanalogous structural transformation patterns, Chap. 15, (ed. Baker, D. R. and Umetsu, N. K.) ACS Symposium Series No. 774., American Chemical Society, Washington, DC
  4. Uraguchi, R., Sato, Y., Nakayama, A., Sukekawa, M., Iwataki, I., Boger, P. and Wakabayashi, K. (1997) Molecular shape similarity of cyclic imides and protoporphyrinogen IX. J. Pesticide Sci., 22, 314-320
  5. Theodoridis, G., Bahr, J. T., Hotzman, F. W., Sehgel, S. and Suarez, D. P. (2000) New geration of protox-inhibiting herbicides, Crop Protection, 19, 533-535 https://doi.org/10.1016/S0261-2194(00)00069-7
  6. Sung, N. D., Ock, H. S., Song, J. H. and Lee, Y. G. (2003) Comparative molecular field analyses (CoMFA) on the growth inhibition activity of N-phenyl-3,4,5,6-tetra-hydrophtalimide and N-phenyl-3,4-dimethylmaleimide Derivatives. Kor. J. Pesti. Sci. 7, 75-82
  7. Sung, N. D., Song, J. H., Yang, S. Y. and Park, K. Y. (2004) Understanding the protox inhibition activity of novel 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy-2-chloro-4-fluorobenzene derivatives using comparative molecular field analysis (CoMFA) methodology. Kor. J. Pesti. Sci. 8, 151-161
  8. Sung, N. D., Ock, H. S., Chung, H. J. and Song, J. H. (2003) Quantitative structure-activity relationships and molecular shape similarity of the herbicidal N-substituted phenyl-3,4-dimethyl-maleimide Derivatives. Kor. J. Pesti. Sci. 7, 100-107
  9. Sung, N. D., Song, J. H. and Park, K. Y. (2004) Understanding the Protox inhibition activity of novel 1-(5-methyl-3-phenyl-isoxazolin-5-structure-activity relationship (HQSAR) methodology. J. Kor. Soc. Appl. Biol. Chem. 47, 351-356
  10. Sung, N. D., Song, J. H. and Park, K. Y. (2004) Understanding the Protox inhibition activity of novel 1-(5-methyl-3-phenyl-isoxazolin-5-yl)methoxy-2-chloro-4-fluorobenzene derivatives using comparative molecular similarity indices analysis (CoMSIA) methodology. J. Kor. Soc. Appl. Biol. Chem. 47, 414-421
  11. Kubinyi, H. (1993) In 3D-QSAR Drug Design, Theory, Methods and Applications. ESCOM. Leiden
  12. Kamoshita, K., Takayama, C., Takahashi, J. and Fujinami, A. (1992) In Rational Approaches to Structure, Activity, and Ecotoxicology of Agrochemicals: Application of the Hansch-Fujita Method to the Design of Imide and carbamate fungicides. Chap. 17., Drabe, W. and Fujita, T. (ed.)., CRC Press, London
  13. Sung, N. D., Yoon, T. Y., Song, J. H. and Jung, H. S. (2005) Three dimensional quantitative structure-activity relationship analyses on the fungicidal activities of new novel 2-alkoxyphenyl-3-phenylthioisoindoline-l-one derivatives using the comparative molecular similarity indices analyses (CoMSIA) methodology based on the different alignment approaches. J. Pesti. Sci. 9, 26-34
  14. Sung, N. D., Yoon, T. Y., Song, J. H. and Jung, H. S. (2005) Three dimensional quantitative structure-activity relationship on the fungicidal activities of new novel 2-alkoxyphenyl-3phenylthioisoindoline-l-one derivatives using the compar- ative molecular field analyses (CoMFA) methodology based on the different alignment approaches. J. Kor. Soc. Appl. Biol. Chem. 48, 82-88
  15. Cramer, R. D., Patterson, D. E. and Bunce, J. D. (1988) Comparative molecular field analysis (CoMFA), I. Effect of shape on the binding of steroids to carrier proteins. J. Am. Chem. Soc. 110, 5959-5967 https://doi.org/10.1021/ja00226a005
  16. Kang, E. K. (2002) Effect of 3-thioalkoxy groups on herbicidal activities of 2-(5-alkoxyphenyl)-3-phenylthioisoindoline-l-one Derivatives. A Thesis for the Degree of Master in Agricultural Science, Chung-nam National University
  17. Tripos Associates, Inc., 1699 S. Hanley Road, Suite 303, St. Louis, MO. USA
  18. Kerr, R. (1994) Parallel helix bundles and ion channels: molecular modeling via simulated annealing and restrained molecular dynamics. Biophys. J. 67, 1501-1515 https://doi.org/10.1016/S0006-3495(94)80624-1
  19. Purcell, W. P. and Singer, J. A. (1967) A brief review and table of semiempirical parameters used in the Huckel molecular orbital method. J. Chem. Eng. Data. 122, 235-246
  20. Marshall, G. R., Barty, C. D., H. E. Bosshard, R. A. Dammkoehler, D. A. Dunn (1979) In Computer-assisted drug design: The conformational parameter in drug design; active analog approach. Olsen, E. C. and Christoffersen, R. E.(eds), Ammerican Chemical Society, Washington, D.C. pp. 205-226
  21. Clark, M., Cramer III, R. D., Jones, D. M., Patterson, D. E. and Simeroth, P. E. (1990) Comparative molecular field analysis (CoMFA). 2. Toward its use with 3D-structural databases. Tetrahedron Comput. Methodol. 3, 47-59 https://doi.org/10.1016/0898-5529(90)90120-W
  22. Cramer, R. D., Bunce, J. D. and Patterson, D. E. (1988) Cross-validation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies. Quant. Struct. -Act. Relat. 7, 18-25 https://doi.org/10.1002/qsar.19880070105