Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

A Study on the Syntheses of Simple Analogs of Tetracycline and Flavonoid

Tetracycline과 Flavonoid의 간단한 유도체 합성에 관한 연구

  • Kim, Hakwon (Department of Chemistry, College of Natural Science, Kyung Hee University)
  • 김학원 (경희대학교 자연과학대학 화학과)
  • Published : 19960800
Download PDF
⟨ Previous Next ⟩

Abstract

This work describes studies aimed at the synthesis of simple analogs of antibiotic tetracycline(TC) and flavonoid. The synthesis of proposed analogs of tetracycline and flavonide has been accomplished from readily available compounds 9 and 15. The 1,3-cyclohexanedione derivative 9 was transformed to the benzoate derivative 12 followed by base-mediated intramolecular benzoylation to give the bicyclic TC-analog 13. The bicyclic TC-analog 25 and the flavonoid-analogs 26 and 27 have been prepared from the quinol derivative 15.

항생물질 tetracycline(TC)과 여러 가지 다양한 활성도를 보이는 flavonoid화합물들의 단순유도체들(13, 25, 26, 27)을 새로운 벙법으로 합성하였다, 먼저, 1,3-cyclohexanedione 유도체로부터 분자내 benzoyl group의 이동 반응을 이용하여 TC의 A, D ring이 유사한 bicyclic compound 13를 합성하였고, 0-methoxy benzaldehyde로부터 TC의 A, C ring이 유사한 bicyclic compound, 25와 chromone을 모핵으로 하는 flavonoid유도체, 26과 27을 합성하였다.

Keywords

References

  1. Burger's Medicinal Cdhemistry(4th ed.) Manfield, E. Wolff(ed.)
  2. Angew. Chem. Int. Ed. v.14 Durckheimer, W.
  3. J. Adm. Chem. Soc. v.90 Korst, J. J.;David, J.;Butler, K.;Bfianco, E. J.;Conover, L. H.;Woodward, R. B.
  4. J. Am. Chem. Soc. v.87 Muxfeldt, H.;Rogalski, W.
  5. Tet. Letter Martin, W.;Hartung, H.;Urbach, H.lDurckheimer, W.
  6. Tet. Letter v.21 Kirchlechner, R.;Rogalski, W.
  7. Comprehensive organic chemistry v.4 Staunton, J.;Sammes, P. G.(ed.)
  8. Investigational New Drugs v.4 Corbet, T. H.;Bissery, M. C.;Wozniak, A.;Plowman, J.;Polin, L.;Tapazoglou, E.;Dieckman, J.;Valeriote, F.
  9. 논문초록 제75차 대한화학회 춘게학술회의 포스터발표 김학원;윤병훈;이은경
  10. Org. Syn. v.45 Larsen, E. H.;Lawesson, S. o.
  11. J. Org. Chem. v.46 Sanifer, R. M.;Bhattacharya, A. K.;Harris, T. M.
  12. J. Chem. Soc. Perkin Trans. Ⅰ Chorn, T. A.;Giles, R. G. F.;Green, I. R.;Hugo, V. I.;Mitchell, P. R. K.;Yorke, S. C.
  13. J. Org. Chem. v.57 Kraus, G. A.;Kirihara, M.
  14. J. Org. Chem. v.39 Shah, V. R.;Bose, J. L.;Shah, R. C.
  15. J. Chem. Soc. Perkin Trans. Ⅰ Pelliciari, R.;Fringuelli, R.;Sisani, E.;Curni, M.
  16. J. Org. Chem. v.50 Rathke, M.;Nowak, M.