Quantitative structure-activity relationships and molecular shape similarity of the herbicidal N-substituted phenyl-3,4-dimethylmaleimide Derivatives

제초성 N-치환 phenyl-3,4-dimethylmaleimide 유도체의 정량적인 구조-활성관계와 분자 유사성

  • Sung, Nack-Do (Division of Applied Biology & Chemistry, Chung-nam National University) ;
  • Ock, Hwan-Suk (Department of Environment & Health System, Daejeon Health Sciences College) ;
  • Chung, Hun-Jun (Department of Environment & Health System, Daejeon Health Sciences College) ;
  • Song, Jong-Hwan (Korea Research Institute of Chemical Technology)
  • 성낙도 (충남대학교 농업생명과학대학 응용생물화학부) ;
  • 옥환석 (대전보건대학 환경보건시스템) ;
  • 정헌준 (대전보건대학 환경보건시스템) ;
  • 송종환 (한국화학연구원 생물의학연구부)
  • Published : 2003.06.30

Abstract

To improve the growth inhibitory activity against the shoot and root of rice plant (Oryza sativa L) and barnyard grass (Echinochloa crus-galli), a series of N-substituted phenyl-3,4-dimethylmaleimdes derivatives as substrates were synthesized and then their the inhibitory activities of protoporphyrinogen oxidase (1.3.3.4), protox were measured. The quantitative structure-activity relationships (QSAR) between structures and the inhibitory activities were studied quantitatively using the 2D-QSAR method. And also, molecular sharp similarity between the substrate derivatives and protogen, substrare of protox enzyme were studied. The activities of the two plants indicated that barnyard grass had a higher activity than the rice plant and their correlation relationships have shown in proportion for each. Accordingly, the results of SARs suggest that the electron donating groups as $R_2=Sub.X$ group will bind to phenyl ring because the bigger surface area of negative charged atoms in the substrate molecule derivatives may increase to the higher the activity against barnyard grass. Based on the molecular shape similarity, when the derivatives and protogen, subsbrate of protox enzyme were superimposed by atom fitting, the similarity indices (S) were above 0.8 level but the correlation coefficients (r) between S values and the activities showed not good.

Keywords

2D-QSAR;N-substituted phenyl-3,4-dimethylmaleimdes;growth inhibitory activity;protox inhibitor;molecular similarity indices

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