Comparative molecular field analysis(CoMFA) on the fungicidal activity of 2-thienyl and 2-furyl substituents in bis-aromatic ${\alpha},{\beta}$-unsaturated ketone derivatives

비스 방향족 ${\alpha},{\beta}$ 불포화 케톤 유도체 중 2-thienyl 및 2-furyl 치환체의 항균활성에 관한 비교분자장 분석(CoMFA)

  • Sung, Nack-Do (Division of Applied Biology & Chemistry, Chung-nam National University) ;
  • Yu, Seong-Jae (Division of Applied Biology & Chemistry, Chung-nam National University) ;
  • Lim, Chi-Hwan (Division of Applied Biology & Chemistry, Chung-nam National University) ;
  • Akamatsu, Miki (Division of Science and Technology of Regional Environment, Faculty of Agriculture, Kyoto University)
  • 성낙도 (충남대학교 농과대학 응용생물화학부) ;
  • 유성재 (충남대학교 농과대학 응용생물화학부) ;
  • 임치환 (충남대학교 농과대학 응용생물화학부) ;
  • 적송미기 (교토대학교 농학부)
  • Published : 1998.09.30

Abstract

Bis-aromatic ${\alpha},{\beta}$-unsaturated ketone derivatives represented as substrate(S) were synthesized and their fungicidal activities in vivo against rice blast(Pyricularia oryzae) and tomato leaf blight(Phytophthora infestans) were examined with the quantitative structure activity relationships(QSAR) using 3D QSAR, comparative molecular field analysis (CoMFA). The 3D CoMFA results and those of 2D QSAR were compared and the results reveal that both results show similar trend. The two important factors, steric and electronic, contribute toward the activity. We assumed that fungicidal activity for rice blast was greatly improved by increasing with positive charge of ${\beta}$-carbon and introduction of bulky derivatives into $R_{2}$ group, while that for tomato leaf blight was improved by decreasing the positive charge of ${\beta}$-carbon and introduction of smaller molecular derivative into $R_{2}$ group. The CoMFA analyses clearly demonstrate its potential in unraveling the steric and electronic features of the molecules through contour maps.

Keywords

bis - aromatic ${\alpha}$;{\beta}$ - unsaturated ketone derivatives;fungicidal activity;CoMFA