Solid-phase synthesis of new fused tetra, penta and hexacyclic β-carboline derivatives

Tetrahedron Letters

Volumn 44, Issue 10, 2003, Pages 2211-2215

  Klein, Gérard ^a   Ostresh, John M ^a   Nefzi, Adel ^a  

^a TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CARBOLINE DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0037416927     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00181-3     Document Type: Article

References (23)

1. Gallop M.A., Barret R.W., Dower W.J., Fodor S.P.A., Gordon E.M. J. Med. Chem. 37:1994;1233.
2. Gordon E.M., Barret R.W., Dower W.J., Fodor S.P.A., Gordon E.M. J. Med. Chem. 37:1994;1385.
3. Thompson L.A., Ellman J.A. Chem. Rev. 96:1996;555.
4. Fruchtel J.S., Jung G. Angew. Chem., Int. Ed. Engl. 35:1996;17.
5. Hermkens P.H.H., Ottenheijm H.C.J., Rees D.C. Tetrahedron. 52:1996;4527.
6. Nefzi A., Ostresh J.M., Houghten R.A. Chem. Rev. 97:1997;449.
7. Ho B.T. J. Pharm. Sci. 61:1972;821.
8. Audia J.E., Evrard D.A., Murdoch G.R., Droste J.J., Nissen J.S., Schenk K.W., Fludzinski P., Lucaites V.L., Nelson D.L., Cohen M.L. J. Med. Chem. 39:1996;2773.
9. Ninan P.T., Insel T.M., Cohen R.M., Cook J.M., Skolnick P., Paul S.M. Science. 218:1982;1332.
10. Mendelson W.B., Cain M., Cook J.M., Paul S.M., Skolnick P. Science. 219:1983;414.
11. Steele J.C.P., Veitch N.C., Kite G.C., Simmonds M.S.J., Warhurst D.C. J. Nat. Prod. 65:2002;85.
12. Wang H., Usui T., Osada H., Ganesan A. J. Med. Chem. 43:2000;1577.
13. Wang H., Ganesan A. Org. Lett. 1:1999;1647.
14. Pictet A., Spengler T. Chem. Ber. 44:1911;2030.
15. Cox E.D., Cook J.M. Chem. Rev. 95:1995;1797.
16. Kaljuste K., Unden A. Tetrahedron Lett. 36:1995;9211.
17. Mayer J.P., Bankaitis-Davis D., Zhang J., Beaton G., Bjergarde K., Andersen C.M., Goodman B.A., Herrera C.J. Tetrahedron Lett. 37:1996;5633.
18. Yang L., Guo L. Tetrahedron Lett. 37:1996;5041.
19. Ostresh J.M., Schoner C.C., Hamashin V.T., Nefzi A., Meyer J.-P., Houghten R.A. J. Org. Chem. 63:1998;8622.
20. Nefzi A., Ostresh J.M., Giulianotti M., Houghten R.A. J. Comb. Chem. 1:1999;195.
21. Acharya A.N., Nefzi A., Ostresh J.M., Houghten R.A. J. Comb. Chem. 3:2001;189.
22. 6) δ 2.83-2.87 (m, 2H), 4.02-4.05 (m, 1H), 6.12 (s, 1H), 6.82-6.88 (m, 2H), 6.95-7.03 (m, 2H), 7.07-7.11 (m, 2H), 7.28-7.28 (m, 2H), 7.42 (d, J=7.70 Hz, 1H), 7.50 (d, J=7.35 Hz, 1H), 9.55 (s, 1H), 10.26 (s, 1H). Reduction procedure: To obtain compounds 2 and 15, the reduction was achieved following the conditions described in Ref. 12. Low purities for compounds 4 and 10 are due to incomplete cyclization and other undetermined side reactions. Attempts to optimize the reaction conditions to drive cyclization to completion are under investigation.
23. Houghten R.A. Proc. Natl. Acad. Sci. USA. 82:1985;5131.