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KMID : 0903520050480010082
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Journal of the Korean Society of Agricultural Chemistry and Biotechnology
2005 Volume.48 No. 1 p.82 ~ p.88
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Three Dimensional Quantitative Structure-Activity Relationship on the Fungicidal Activities of New Novel 2-Alkoxyphenyl-3-phenylthioisoindoline-1-one Derivatives Using the Comparative Molecular Field Analyses (CoMFA) Methodology Based on the Different Alignment Approaches
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Seong Nak-Do
Yoon Tae-Yong
Song Jong-Hwan
Jeong Hoon-Sung
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Abstract
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3D QSAR studies for the fungicidal activities against resistive phytophthora blight (RPC; 95CC7303) and sensitive phytophthora blight (Phytopthora capsici) (SPC; 95CC7105) by a series of new 2-alkoxyphenyl-3-phenylthioisoindoline-1-one derivatives (X: A=propynyl & B=2-chloropropenyl) were studied using comparative molecular field analyses (CoMFA) methodology. The CoMFA models were generated from the two different alignment, atom based fit (AF) alignment and field fit (FF) alignment. The atom based alignment exhibited a higher statistical results than that of field fit alignment. The best models, A3 and A7 using combination fields of H-bond field, standard field, LUMO and HOMO molecular orbital field as additional descriptors were selected to improve the statistic of the present CoMFA models. The statistical results of the two models showed the best predictability of the fungicidal activities based on the cross-validated value q2 (r2cv.=RPC: 0.625 & SPC: 0.834), non cross-validated value (r2ncv.=RPC: 0.894 & SPC: 0.915) and PRESS value (RPC: 0.105 & SPC: 0.103), respectively. Based on the findings, the predictive ability and fitness of the model for SPC was better than that of the model for RPC. The fugicidal activities exhibited a strong correlation with steric (66.8~82.8%), electrostatic (10.3~4.6%) and molecular orbital field (SPC: HOMO, 12.6% and RPC: LUMO, 22.9%) factors of the molecules. The novel selective character for fungicidal activity between two fungi depend on the positive charge of ortho, meta-positions on the N-phenyl ring and size of hydrophilicity of a substituents on the S-phenyl ring.
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KEYWORD
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3D-QSAR, 2-alkoxyphenyl)-3-phenylthioisoindoline-1-one, fungicidal activity, resistant & sensitive phytophthora blight (Phytopthora capsici), different alignment approaches, CoMFA model
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