Studies on the reactions of 2,3-diketopyrido[4,3,2-de] quinolines with amino acids and amino esters

Heterocyclic Communications

Volumn 6, Issue 6, 2000, Pages 495-500

  Shao, Huawu ^a   Ding, Qizhu ^a   Lown, J William ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034551585     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.2000.6.6.495     Document Type: Article

References (30)

1. P. J. Scheuer, Science 248, 173(1990).
2. (a) N. S. Burres, S. S. Sazesh, G. P. Gunawardana and J. J. Clement, Cancer Res. 49, 5267 (1989).
3. (b) T. F. Molinski, Chem. Rev. 93, 1825 (1993).
4. (c) I. B. Taraporewala, J. W. Cessac, T. C. Chanh, A. V. Delgado, R. F. Schinazi, J . Med. Chem. 35, 2774 (1992).
5. (d) B. S. Davidson, Chem. Rev. 93, 1771 (1993).
6. (e) M. Alvarez and J. A. Joule, Heterocycles 34, 2385 (1992).
7. (a) G. P. Gunawardana, F. E. Koehn, A. Y. Lee, J. Clardy, H. Y. He and D. J. Faulkner, J. Org. Chem. 57, 1523 (1992).
8. (b) M. A. Cuifolini, Y. C. Shen and J. Bishop, J. Am. Chem. Soc. 117, 12460 (1995).
9. (c) L. A. McDonald, G. S. Eldridge, L. R. Barrows and C. M. Ireland, J. Med. Chem. 37, 3819 (1994).
10. (d) F. Guillier, F. Nivoliers, C. Cochennec, A. Godard, F. Marsais and G. Queguiner, Synth. Commun. 26, 4421 (1996).
11. . (a) J. Kobayashi, M. Tsuda. A. Tanabe, M. Ishibashi, J. F. Cheng, S. Yamamura and T. Sasaki, J. Nat. Prod. 54, 1634 (1991).
12. (b) M. A. Ciufolini and Y. C. Shen, Tetrahedron Lett. 36, 4709 (1995).
13. (c) A. Plubrukarn and B. S. Davidson, J. Org. Chem. 63, 1657 (1998).
14. (a) C. E. Muller, U. Geis, B. Grahner, W. Lanzner and K. Egger, J. Med. Chem. 39, 2482 (1996).
15. (b) C. Ede, P. Schupp, P. Proksch, V. Wray, K. Steube, C. E. Muller, W. Frobenius, M. Herderich and R. W. M. van Soest, J. Nat. Prod. 61, 301 (1998).
16. (c) J. P. Michael and G. Pattenden, Angew. Chem., Int. Ed. Engl. 32, 1 (1993).
17. (a) J. Kobayashi, J. F. Cheng, M. R. Walchli, H. Nakamura, Y. Hirata, T. Sasaki and Y. Ohizumi, J. Org. Chem. 53, 1800 (1988).
18. (b) M. A. Ciufolini and N. E. Byrne, J. Am. Chem. Soc. 113, 8016 (1991).
19. (a) M. J. Bishop, M. A. Ciufolini, J. Am. Chem. Soc. 114, 10081 (1992).
20. (b) G. P. Gunawardana, S. Kohmoto, S. P. Gunasekera, O. J. Mcconnell and F. E. Koehn, J. Am. Chem. Soc. 110, 4856 (1988).
21. (a) R. L. Zhao and J. W. Lown, Synth. Commun. 27, 2103 (1997).
22. (b) R. L. Zhao, B. Oreski and J. W. Lown, Bioorg. Med. Chem.Lettt. 6, 2169 (1996).
23. Q. Z. Ding, R. L. Zhao and J. W. Lown, Heterocyclic Commun. 3, 489 (1997).
24. (a) Q. Z. Ding, K. Chichak and J. W. Lown, Current Medicinal Chemistry 6, 1 (1999).
25. (b) Q. Z. Ding and J. W. Lown, Heterocyclic Commun. 4, 535 (1998).
26. Q. Z. Ding, G. F. Jia and J. W. Lown, Anti-Cancer Drug Design 15, 99 (2000).
27. Q. Z. Ding and J. W. Lown, Heterocyclic Commun. 4, 125 (1998).
28. Q. Z. Ding and J. W. Lown, J. Org. Chem. 64, 7965 (1999).
29. General experimental procedure for the amination reaction summarized in Table 1: A solution of 10 mg (0.034 mmol) of 1H-2,3-diketopyrido[4,3,2-de]quinolines (1) was suspended in 8 ml of water and the pH value was adjusted to 10 with triethylamine, then 4 mL of tetrahydrofuran was added, followed by the amino acid 7.5 mg(0.1 mmol, Table 1, entry 6). The resulting mixture was stirred at room temperature for 72 hours. A red product formed in the solution. After removing the solvent under vacuum, the residue was extracted with chloroform (20 mL × 2) and the crude product was purified by flash chromatography on silica gel(Merck, 230-400 mesh) using a solvent mixture of ethyl acetate/hexane(1:1 then 4:1) and then ethyl acetate. The red product was fully characterized spectroscopically.
30. 6Cl: C, 51.85; H, 4.06; N, 10.67. Found: C, 51.96; H, 4.07; N, 10.19.