Structure-Activity Relationship (Ⅰ). Conformational Analysis of 3-Phenyl-5,5-dimethyloxazolidine-2,4-diones and their Antifungal Activities

구조-활성 관계 (제 1 보). 3-Phenyl-5,5-dimethyloxazolidine-2,4-diones 와 그들의 Antifungal Activity 에 관한 형태 분석

  • Park Seongsik (Department of Chemistry, Kyungsung University) ;
  • Yoh Soo-Dong (Department of Chemistry Education, Kyungpook National University) ;
  • Chung Duk-Young (Department of Chemistry Education, Kyungpook National University)
  • 박성식 (경성대학교 이과대학 화학과) ;
  • 여수동 (경북대학교 화학교육과) ;
  • 정덕영 (경북대학교 화학교육과)
  • Published : 19900900

Abstract

The relationship between chemical structure and antifungal activity of benzene ring substituents of 3-phenyl-5,5-dimethyloxazolidine-2,4-diones is studied by testing of model compounds and use of conformational data. The analysis revealed a number of structural features as essential for the antifungal effect: (1) the presence of an intact -NCO group and benzene moiety; (2) the distance between para substituents and the N atom within the 5.32∼5.37${\AA}$ range; (3) the distance between substituents X3 and X4, in the interval 5.59 ∼ 5.77 ${\AA}$ for the active analogues.

3-phenyl-5,5-dimethyloxazolidine-2,4-dione에 대한 형태 분석을 통하여 구조-활성 관계를 검토하였다. Antifungal Activity에 대한 구조적인 특징으로 활성기인 amide group(-NCO)와 벤젠 moiety가 존재하며, 강한 활성을 나타내는 유사체의 N원자와 para 치환기 간의 공간거리 N-X$_4$는 5.32∼5.37${\AA}$, 3,5-치환기 간의 거리 X$_3$-X$_5$는 5.59 ∼ 5.77 ${\AA}$을 나타내었다.

Keywords

References

  1. Agric. Biol. Chem. v.35 A. Fujinami;T. Ozaki;S. Yamamoto
  2. J. Chem. Soc. Perkin Trans.2 E. Osawa;G. Szatontai;A. Tsurumoto
  3. J. Am. Chem. Soc. v.95 E. M. Engler;J. D. Andose;P. V. R. Schleyer
  4. J. Am. Chem. Soc. v.99 L. S. Bartell
  5. J. Am. Chem. Soc. v.99 N. L. Allinger
  6. Chem. Prog. Exch., program No.395; Program MMPMI Allinger, N. L;Yuh, Y. H.;Quanta
  7. Chem. Pharm. Bull. v.32 C. Yamagami;N. Takao;M. Tanaka;K. Horisaka;S. Asada;T. Fujita
  8. Principles of Medicinal Chemistry W. O. Foye
  9. J. Med. Chem. v.26 H. Van de Waterbeem;B. Testa
  10. J. Med. Chem. v.27 M. Froimowitz
  11. Mol. Pharm. v.14 T. D. Paulis;D. Kelder;S. B. Ross
  12. Agric. Biol. Chem. v.36 A. Fujinami;T. Ozaki;K. Nodera;K. Tanaka
  13. Agric. Biol. Chem. v.38 H. Ohkawa;Y. Hisada;N. Fujiwara;J. Miyamoto
  14. J. Chem. Soc. Perkin Trans.2 Z. Taira;C. Takayama;H. Terada
  15. Molecular Orbital theory in Drug Research L. B. Kier
  16. J. Theor. Biol. v.41 H. J. R. Weintraub;A. J. Hopfinger
  17. J. Med. Chem. v.22 G. M. Crippen
  18. J. Biochem. v.76 K. Yamamoto
  19. Molecular Mechanics U. Burkert;N. L. Allinger