Synthesis and evaluation of new 6-hydroximinosteroid analogs as cytotoxic agents

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 14, 2007, Pages 4722-4740

  Poza, Javier ^a   Rega, Miriam ^a   Paz, Vanessa ^a   Alonso, Beatriz ^a   Rodríguez, Jaime ^a   Salvador, Nélida ^b   Fernández, Antonio ^b   Jiménez, Carlos ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

^b Instituto Biomar SA   (Spain)

Author keywords

Cytotoxic activity; Hydroximinosteroid; Tumor cell lines

Indexed keywords

16BETA ACETOXY 3BETA HYDROXY 6 HYDROXYIMINOCHOLEST 4 ENE; 1ALPHA DIACETOXY 5BETA,6BETA EPOXYCHOLESTANE; 1ALPHA HYDROXY 6 HYDROXIMINOCHOLEST 4 EN 3 ONE; 1ALPHA,2ALPHA EPOXYCHOLESTA 4,6 DIEN 3 ONE; 1ALPHA,3BETA DIACETOXY 5ALPHA HYDROXYCHOLESTAN 6 ONE; 1ALPHA,3BETA DIACETOXY 5ALPHA,6ALPHA EPOXYCHOLETANE; 1ALPHA,3BETA DIACETOXYCHOLEST 4 EN 6 ONE; 1ALPHA,3BETA DIHYDROXYCHOLEST 4 EN 6 ONE; 1ALPHA,3BETA DIHYDROXYCHOLEST 5 ENE; 3BETA ACETOXY 4BETA,5BETA EPOXY 6 HYDROXIMINOCHOLESTANE; 3BETA ACETOXY 4BETA,5BETA EPOXYCHOLESTAN 6 ONE; 3BETA,16BETA DIACETOXY 6 HYDROXIMINOCHOLEST 4 ENE; 3BETA,4BETA METHYLEHTYLIDENE BIS(OXY 5ALPHA CHOLESTAN 6ALPHA OL); 3BETA,4BETA METHYLETHYLIDENE BIS(OXYCHOLEST 5 ENE); 3BETA,7ALPHA DIHYDROXY 6 HYDROXIMINOCHOLEST 4 ENE; 4BETA ACETOXYCHOLEST 5 EN 3BETA OL; 4BETA,5BETA EPOXY 3BETA HYDROXY 6 HYDROXYIMINOCHOLESTANE; 4BETA,5BETA EPOXY 3ETA HYDROXYCHOLESTAN 6 ONE; 5 CHOLESTENE 3BETA,4BETA DIOL; 5ALPHA FLUORO 3BETA HYDROXY 6 HYDROXIMINOCHOLESTANE; 5ALPHA FLUORO 6 HYDROXIMINO 2ALPHA,3ALPHA CHOLESTANEDIOL; 5ALPHA FLUORO 6 HYDROXIMINO 2ALPHA,3BETA CHOLESTANEDIOL; 5ALPHA FLUORO 6 HYDROXIMINOCHOLESTAN 3 ONE; 6 HYDROXIMINO 4 HYDROXYCHOLEST 4 EN 3 ONE; 6 HYDROXIMINO 5BETA CHOLESTAN 3BETA,4BETA DIOL; 6 HYDROXIMINOCHOLEST 4 EN 1ALPHA,3BETA DIOL; 7ALPHA HYDROXY 6 HYDROXIMINOCHOLEST 4 EN 3 ONE; CHOLESTA 1,4,6 TRIEN 3 ONE; CHOLESTANE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SYNTHESIS; FLUORINATION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; OXYGENATION; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

CELL LINE, TUMOR; CELL SURVIVAL; CYTOTOXINS; EPOXY COMPOUNDS; FLUORINE; HUMANS; HYDROXYLATION; IMINES; MOLECULAR STRUCTURE; OXYGEN; STEROIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34249817878     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.05.003     Document Type: Article

References (26)

1. Rodríguez J., Nuñez L., Peixinho S., and Jiménez C. Tetrahedron Lett. 38 (1997) 1833-1836
2. Holland H.L., Kumaresan S., Tan L., and Njar V.C.O. J. Chem. Soc., Perkin Trans. 1 (1992) 585-587
3. Blickenstaff R.T. Antitumor Steroids (1992), Academic Press, San Diego
4. Chandigarh R., Jinda D.P., Minu M., and Gupta R. Arzneimittel Forschung 54 (2004) 551-556
5. Deive N., Rodri{dotless}́guez J., and Jiménez C. J. Med. Chem. 44 (2001) 2612-2618
6. Fürst A., Ludvik L., and Meier W. Helv. Chim. Acta 64 (1981) 1870-1892
7. Meizheng L., Biao Y., Xiangyang W., and Yongheng H. Carbohyd. Res. 329 (2000) 745-754
8. Over D., Bardet M., and Marchon J.-C. Mag. Reson. Chem. 33 (1995) 224-227
9. Hanson J.R., and Truneh A. J. Chem. Soc., Perkin Trans. 1 (1988) 2001-2003
10. Templeton J.F., Kumar V.P.S., Kim R.S., and LaBella F.S. J. Chem. Soc., Perkin Trans. 1 (1987) 1361-1368
11. Ramirez J., Osvaldo M., Centurión T., Gros E., and Galagovsky L. Steroids 65 (2000) 329-337
12. Rami{dotless}́rez J., Gros E., and Galagovsky L. Tetrahedron 56 (2000) 6171-6180
13. Numazawa M., Hoshi K., and Oshibe M. J. Steroid Biochem. Mol. Biol. 39 (1991) 959-966
14. Glotter E., and Mendelovici M. J. Chem. Res. Miniprint. (1991) 2201-2234
15. Tabares da Silva E.J., Roleira F.M.F., Sa e Melo M.L., Campos Neves A.S., Paixao J.A., De Almeida M.J., Silva M.R., and Andrade C.R.L. Steroids 67 (2002) 311-319
16. Di Filippo M., Fezza F., Izzo I., De Riccardis F., and Sodano G. Eur. J. Org. Chem. (2000) 3247-3252
17. Goad L.J., and Akihisa T. Analysis of Sterols (1997), Chapman & Hall, London
18. Salvador J.A.R., Sa e Melo M.L., and Campos Neves A.S. Tetrahedron Lett. 38 (1997) 119-122
19. Li D., and Spencer L. Steroids 65 (2000) 529-535
20. Tanaka J., Trianto A., Musman M., Issa H.H., Ohtani I.I., Ichiba T., Higa T., Yoshida W.Y., and Scheuer P.J. Tetrahedron 58 (2002) 6259-6266
21. Sabitha G., Babu S., Rajkumar M., Reddy C.S., and Yadav J.S. Tetrahedron Lett. 42 (2001) 3955-3958
22. Mitome H., Shirato N., Hoshino A., Miyaoka H., Yamada Y., and Van Soest R.W.M. Steroids 70 (2005) 63-72
23. Musumeci D., Roviello G.N., and Sica D. Steroids 69 (2004) 173-179
24. Williams J., Chai R., and Wright D. Steroids 67 (2002) 1041-1044
25. Salvador J.A.R., Sa e Melo M.L., and Campos Neves A.S. Tetrahedron Lett. 37 (1996) 687-690
26. Mosmann T. J. Immunol. Methods 65 (1983) 55-63