CoMFA and CoMSIA Analysis on the Fungicidal Activity against Damping-off (Pythium ultimum) with N-phenylbenzenesulfonamide Analogues

N-phenylbenzenesulfonamide 유도체들에 의한 모잘록병균 (Pythium ultimum)의 살균활성에 관한 CoMFA 및 CoMSIA분석

  • Jang, Seok-Chan (Division of Applied Biology and Chemistry, College of Agriculture and Life Sciences, Chungnam National University) ;
  • Kang, Kyu-Young (Division of Applied Life Science, Gyeongsang National University) ;
  • Sung, Nack-Do (Division of Applied Biology and Chemistry, College of Agriculture and Life Sciences, Chungnam National University)
  • 장석찬 (충남대학교 농업생명과학대학 응용생물화학부) ;
  • 강규영 (경상대학교 농업생명과학대학 환경생명화학) ;
  • 성낙도 (충남대학교 농업생명과학대학 응용생물화학부)
  • Published : 2007.03.30

Abstract

Three-dimensional quantitative structure-activity relationships (3D-QSARs) on the fungicidal activity against damping-off (Pythium ultimum) with N-phenylbenzenesulfonamide and N-phenyl-2-thienylsulfonamide analogues (1-34) were studied quantitatively using CoMFA (comparative molecular field analysis) and CoMSIA (comparative molecular similarity indeces analysis) methodologies. On the whole, the statistical qualities of CoMSIA models with field fit alignment (FF1-FF5) were slightly higher than that of atom based fit alignment (AF1-AF5) but, the deviations of statistical quality between two alignments in case of CoMFA models were slightly lower. The statistical results of CoMFA and CoMSIA model showed that the optimized CoMSIA model (FF1: $r_{cv.}^2\;(q^2)=0.674$ & $r_{ncv.}^2=0.964$) for damping-off is better predictability and fitness for fungicidal activities than CoMFA model (AF5: $r_{cv.}^2\;(q^2)=0.616$ & $r_{ncv.}^2=0.930$). The fungicidal activities according to the information of the CoMSIA (FF1) model were dependence upon the electrostatic and hydrophobic field of the N-phenylbenzene sulfonamide analogues. Therefore, from the results of graphical analyses on the contour maps with CoMSIA (FF3) model, it is expected that the characters of R4-substituent on the N-phenyl ring as hydrophobic and hydrogen bond acceptor will be contributed to the fungicidal activity against damping-off.

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