Synthesis and DNA photo-cleaving activity of novel heterocyclic N-oxide - Acridine hybrid molecules

Heterocycles

Volumn 42, Issue 1, 1996, Pages 31-34

  Sako, Magoichi ^a   Takeda, Yoshifumi ^a   Hirota, Kosaku ^a   Maki, Yoshifumi ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001818372     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-94-S2     Document Type: Article

References (17)

1. For a review, see: Y. Maki and M. Sako, J. Syn. Org. Chem., 1994, 52, 149.
2. M. Sako, T. Makino, Y. Kitade, K. Hirota, and Y. Maki, J. Chem. Soc., Perkin Trans. I, 1992, 1801 and preceding papers.
3. M. Sako, K. Nagai, and Y. Maki, J. Chem, Soc., Chem. Commun., 1993, 750.
4. Unpublished result.
5. R. P. Herzberg and P. B. Dervan, J. Am. Chem. Soc., 1982, 104, 313; J. W. Lown and A. V. Joshua, J. Chem. Soc., Chem. Commun., 1982, 1298; R. Kuroda and M. Shinomiya, Biochem. Biophys. Res. Commun., 1991, 181, 1266.
6. R. P. Herzberg and P. B. Dervan, J. Am. Chem. Soc., 1982, 104, 313; J. W. Lown and A. V. Joshua, J. Chem. Soc., Chem. Commun., 1982, 1298; R. Kuroda and M. Shinomiya, Biochem. Biophys. Res. Commun., 1991, 181, 1266.
7. R. P. Herzberg and P. B. Dervan, J. Am. Chem. Soc., 1982, 104, 313; J. W. Lown and A. V. Joshua, J. Chem. Soc., Chem. Commun., 1982, 1298; R. Kuroda and M. Shinomiya, Biochem. Biophys. Res. Commun., 1991, 181, 1266.
8. E. C. Taylor, Y. Maki, and A. McKillop, J. Org. Chem., 1972, 10, 1601.
9. Y. Maki, M. Sako, and E. C. Taylor, Tetrahedron Lett., 1971, 4271.
10. All new compounds described here gave satisfactory microanalytical results and spectral data consistent with their structures.
11. G. D. Daves, Jr., R. K. Robins, and C. C. Cheng, J. Am. Chem. Soc., 1962, 84, 1724.
12. Although detailed mechanism is not clear at present, it is proposed that participation of Cg-carbonyl group with carboxyl group in the side chain plays an important role in the photo-decarboxylation.
13. The amide derivative (11) was prepared by acid-hydrolysis of the corresponding 9-cyanomethyl derivative in 93% yield.
14. J. B. Hansen and O. Buchardt, J. Chem. Soc., Chem. Commun., 1983, 162; O. Buchardt, M. Egholm, G. Karup, and P. E. Nielsen, ibid., 1987, 1696.
15. J. B. Hansen and O. Buchardt, J. Chem. Soc., Chem. Commun., 1983, 162; O. Buchardt, M. Egholm, G. Karup, and P. E. Nielsen, ibid., 1987, 1696.
16. M. Sako, S. Ohara, K. Hirota, and Y. Maki, Chem. Pharm. Bull., 1991, 39, 195.
17. H = 15.0 G.