Synthesis and antitumoral evaluation of indole alkaloid analogues containing an hexahydropyrrolo[1′,2′,3′:1,9a,9]imidazo[1,2-a]indole skeleton

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 20, 2008, Pages 9313-9322

  Ventosa Andrés, Pilar ^a   González Vera, Juan A ^a   Valdivielso, Ángel M ^a   Teresa Garcia Lopez M ^a   Herranz, Rosario ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

Amino nitriles; Cytotoxicity; Indole alkaloids; Inhibition of EGFR; Inhibition of HIF 1

Indexed keywords

IMIDAZOLE DERIVATIVE; INDOLE ALKALOID; PYRROLE DERIVATIVE;

ADDITION REACTION; ANTINEOPLASTIC ACTIVITY; ARTICLE; BROMINATION; CANCER CELL CULTURE; CONTROLLED STUDY; CYCLOADDITION; DRUG SYNTHESIS; HUMAN; HUMAN CELL;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; INDOLE ALKALOIDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITRILES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 53249091837     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.08.070     Document Type: Article

References (32)

1. González-Vera J.A., García-López M.T., and Herranz R. Org. Lett. 6 (2004) 2641-2644
2. Greig N.H., Pei X.-F., Soncrant T.T., Ingram D.K., and Brossi A. Med. Res. Rev. 15 (1995) 3-31
3. Tan G.H., Zhu X., and Ganesan A. Org. Lett. 5 (2003) 1801-1803
4. Wang H., Gloer J.B., Wicklow D.T., and Dowd P.F. J. Nat. Prod. 61 (1998) 804-807
5. Hochlowski J.E., Mullally M.M., Spanton S.G., Whittern D.N., Hill P., and McAlpine J.B. J. Antibiot. 46 (1993) 380-386
6. Birch A.J., and Russell R.A. Tetrahedron 28 (1972) 2999-3008
7. Takase S., Kawai Y., Uchida I., Tanaka H., and Aoki H. Tetrahedron 41 (1985) 3037-3048
8. Ohmomo S., Utagawa S., and Abe M. Agric. Biol. Chem. 41 (1977) 2097-2098
9. Shiono Y., Akiyama K., and Hayashi H. Biosci. Biotechnol. Biochem. 64 (2000) 103-110
10. Shinohara C., Hasumi K., Takei Y., and Endo A. J. Antibiot. 47 (1994) 163-167
11. Müllbacher A., Waring P., Tiwari-Palni U., and Eichner R.D. Mol. Inmunol. 23 (1986) 231-235
12. Lebsack A.D., Link J.T., Overman L.E., and Stearns B.A. J. Am. Chem. Soc. 124 (2002) 9008-9009
13. Kamenecka T.M., and Danishefsky S.J. Chem. Eur. J. 7 (2001) 41-63
14. Umezawa K., Ikeda Y., Uchihata Y., Naganawa H., and Kondo S. J. Org. Chem. 65 (2000) 459-463
15. Nokada M., Sato I., Cho S.J., Iwata H., Nishio T., Dubnau D., and Sakagami Y. Nat. Chem. Biol. 1 (2005) 23-24
16. Chang R.S., Lotti V.J., Monaghan R.L., Birnbaum J., Stapley E.O., Goetz M.A., Albers-Schonberg G., Patchett A.A., Liesch J.M., Hensens O.D., and Springer J.P. Science 230 (1985) 177-179
17. Wong S.M., Musza L.L., Kydd G.C., Kullnig R., Gillum A.M., and Cooper R. J. Antibiot. 46 (1993) 545-553
18. Belofsky G.N., Anguera M., Jensen P.R., Fenical W., and Kock M. Chem. Eur. J. 6 (2000) 1355-1360
19. Fujimoto H., Negishi E., Yamaguchi K., Nishi N., and Yamazaki M. Chem. Pharm. Bull. 44 (1996) 1843-1848
20. Jiao R.H., Xu S., Liu J.Y., Ge H.M., Ding H., Xu C., Zhu H.L., and Tan R.X. Org. Lett. 8 (2006) 5709-5712
21. Nakao Y., Kuo J., Yoshida W.Y., Kelly M., and Scheuer P.J. Org. Lett. 5 (2003) 1387-1390
22. González-Vera J.A., García-López M.T., and Herranz R. J. Org. Chem. 70 (2005) 8971-8976
23. González-Vera J.A., García-López M.T., and Herranz R. J. Org. Chem. 72 (2007) 5395-5398
24. González-Vera J.A., García-López M.T., and Herranz R. Tetrahedron 63 (2007) 9229-9234
25. Movassaghi M., and Schmidt M.A. Angew. Chem. Int. Ed. 46 (2007) 3725-3728
26. Roberge M., Berlinck R.G., Xu L., Anderson H.J., Lim L.Y., Curman D., Stringer C.M., Friend S.H., Davies P., Vincent I., Haggarty S.J., Kelly M.T., Britton R., Piers E., and Andersen R.J. Cancer Res. 58 (1998) 5701-5706
27. Fan F., and Wood K.V. Assay Drug Dev. Technol. 5 (2007) 127-136
28. Han Y., Caday C.G., Nanda A., Cavenee W.K., and Huang H.J. Cancer Res. 56 (1996) 3859-3861
29. Mu D., Chang Y.S., Vexler Z.S., and Ferriero D.M. Exp. Neurol. 195 (2005) 407-415
30. Vigushin D.M., Ali S., Pace P.E., Mirsaidi N., Ito K., Adcock I., and Coombes R.C. Clin. Cancer Res. 7 (2001) 971-976
31. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107-1112
32. Shoemaker R.H. Nat. Rev. Cancer 6 (2006) 813-823