Synthesis of 1N-alkyl-2-amino-3-ethoxycarbonyl-pyridino [2,3-f]indole-4,9-dione derivatives (I)

1N-알킬-2-아미노-3-에톡시카르보닐-피리디노 [2,3-f]인돌-4,9-디온 유도체의 합성 (I)

  • 서명은 (이화여자대학교 약학대학) ;
  • 신성희 (이화여자대학교 약학대학)
  • Published : 1997.10.01

Abstract

The 6,7-dichlorquinoline-5,8-dione was reacted with ${alpha}$-cyanoacetic acid ethyl ester in ammonia solution to yield 6-(${alpha}$-cyano-${alpha}$-ethoxycarbonyhnethyl)-7-chloroquinoline- 5,8-dione (compound I). When this compound was reacted with some alkyl amines (methylamine, ethylamine, isopropylamine, etc) 2-amino-3-ethoxycarbonyl-N-alkyl-pyridino[2,3-f]indole-4,9-diones (compounds II a-e) were obtained.

Keywords

References

  1. J. Med. Chem. v.29 Streptonigrin. 1. Structure-Activity Relationships among simple Bicyclic Analogues. Rate Dependence of DNA Degradation on Quinone Reduction Potential. Iftikhar A.;Shaikh;Francis Johnson.;Arthur P. Grollman
  2. J. Chem. Education v.70 Antitumor Drugs as DNA Intercalators. UlfPindur.;Manfred Haber;Kristin Sattler
  3. Annu. Rev. Biophys. Bioeng. v.10 Berman, H. M.;Young, P. R.
  4. Principles of Nucleic Acid Structure Saenger, W.
  5. v.6 Bioactive Molecules Lown, J. W.
  6. J. Mol. Biol. v.286 DNA-Drug interaction. The crystal structure of d(CGATCG) complexed with Daunomycin. Madeleine H.;Moore.;William N.;Hunter. Beatrice Langlois;Olga kennard
  7. Yakhak Hoeji v.35 Synthesis of benz[f]indole-4.9-dione derivatives via intramolecular cyclization. Sang-Hee Shin;Myung-Eun Suh
  8. J. Am. Chem. Soc. v.82 Quinolinequinones. V. 6-chloro and 7-chloro-5,8-quinoline-quinones Y. T. Pratt
  9. Yakugaku Zasshi v.90 Studies on Quinones. On the reaction of Naphthoquinone derivatives with active methylene compounds. The craven reaction Akatsuka, M.
  10. J. Am. Chem. Soc. v.84 Quinolinequinones. Ⅵ. Reactions with Aromatic Amines Y. T. Pratt
  11. J. Org. Chem. v.27 Quinolinequinones. Ⅵ. Reactions with Aromatic Amines. Y. T. Pratt
  12. Synthesis of quinoid bispyrrocolines and bisnaphthofurans from chloranil v.14 J. Sci. Ind. Research(India) R. V. Acharya;B. D. Tilaku;M. R. Venkiteswaran
  13. J. Sci. Ind. Research(India) Quinone Series. ⅩⅢ. Synthesis of naphthoquinofuranopyrrocolinequinones and mono-and dipyrrocolinequinones. R. V. Acharya;M. S. Matkiur;B. Suryanarayana;B. D. Tilaku;R. Venkiteswara
  14. J. Sci. Ind. Research(India) Quinone Series. ⅩⅢ. synthesis of cellulose acetate dyes from 2.3-dichloro-1.4-naphthoquinone and chloranil. M. S. Mathur;u. B. D. Tilak
  15. Current Sci. (India) Pyridinium betaines from 2.3-dichloro-1.4-naphthoquinone a new type of vat dyes. B. Suryanarayana;u. B. D. Tilak
  16. J. Org. Chem. v.19 Reaction of Naphthoquinones with Malonic ester and Its Analogs. Ⅱ. Reactions with Acetoacetic Ester and Its Analogs. Ⅱ. Reactions with Acetoacetic Ester and Pyridine or Quinoline E. F. Pratt;R. W. Luckerbaugh;u. R. L. Erickson
  17. J. Org. Chem. v.30 The Reaction of 2.3-Dichloronaphthoquinone with Naclo:hiles J. A. Van Allen;G. A. Reynolds;u, R. E. Adel
  18. J. Org. Chem. v.24 Reaction of 2.3-Dichloro-1.4-Naphthoquinone with 2-Aminopyridine and Related Amines. William L. Mosby;Richard J. Boyle
  19. J. Org. Chem. v.26 Naphthoquinone chemistry. 6H. 11H-Benzo[f]pyridop[a]-benzimidazole-6.11-dione. Willam L. Mosby
  20. J. Org. Chem. v.25 Studies in the Juglone Series. Ⅳ. the Addition of Aniline and Toluene-ρ-thiol to 5-Substituted 1.4-Na-Phthoquinones. J. W. McLeod;R. H. Thomson
  21. J. Org. Chem. v.28 The Synthesis of some New Heterocyclic Quinones J. A. Van Allen;u. G. Reynold
  22. J. Pharm. Soc. Japan. v.90 Quinones. 4. Reaction of Naphthoquinone derivatives with 2-Aminothiophenol M. Akatsuka;u. S. Yoshinage