New aromatic esters of progesterone as antiandrogens

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 19, Issue 2, 2004, Pages 99-105

  Bratoeff, Eugene ^a   Ramírez, Elena ^a   Flores, Eugenio ^a   Sanchez M ^b   Heuze, Ivonne ^b   Cabeza, Marisa ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b DEPARTAMENTO DE SISTEMAS BIOLÓGICOS   (Mexico)

Author keywords

5 reductase inhibition; Androgen receptor; Binding affinity; Novel steroids; Prostate growth

Indexed keywords

4 BROMO 17ALPHA (4 BROMOBENZOYLOXY) 4 PREGNENE 3,20 DIONE; 4 BROMO 17ALPHA (4 CHLOROBENZOYLOXY) 4 PREGNENE 3,20 DIONE; 4 BROMO 17ALPHA (4 FLUOROBENZOYLOXY) 4 PREGNENE 3,20 DIONE; 4 BROMO 17ALPHA (4 TULUOYLOXY) 4 PREGNENE 3,20 DIONE; ANDROSTANOLONE; ANTIANDROGEN; AZASTEROID; BROMINE; CHLORINE; ESTER DERIVATIVE; FINASTERIDE; PROGESTERONE DERIVATIVE; STEROID 5ALPHA REDUCTASE; TESTOSTERONE; UNCLASSIFIED DRUG;

ADOLESCENT; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG STRUCTURE; GONADECTOMY; HAMSTER; IC 50; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; ORGAN WEIGHT; PRIORITY JOURNAL; PROSTATE; SEMINAL VESICLE;

ANDROGEN ANTAGONISTS; ANDROGENS; ANIMALS; CRICETINAE; HYDROGEN-ION CONCENTRATION; KINETICS; MALE; MESOCRICETUS; ORCHIECTOMY; ORGAN SIZE; PROGESTERONE; PROSTATE; TESTOSTERONE; TESTOSTERONE 5-ALPHA-REDUCTASE;

ANIMALIA; CRICETINAE;

EID: 2942511912     PISSN: 14756366     EISSN: None     Source Type: Journal    
DOI: 10.1080/14756360310001650246     Document Type: Article

References (22)

1. Mallamo, J., Pilling, G., Wetzel, J., Kowalczyc, P.J., Bell, M.R., Kulling, R.K., Batzold, F.H., Juniewicz, P.E., Winneker, R.C. and Luss, H.R. (1991) J. Med. Chem. 35, 1663-1670.
2. Labrie, C., Trudel, C., Lee, S., Martel, C., Cout, J. and Labrie, F. (1991) Endocrinology 128, 1163-1167.
3. Santen, R. (1989) Intl. J. Androl. 12, 165-168.
4. Brooks, R., Berman, C., Nguyen, C., Prahalada, S., Primka, R.L., Rasmusson, G.H. and Slater, E.E. (1991) Prostate 18, 215-219.
5. Bruchowsky, N., Rennie, P.S., Bratzold, F.H., Goldenberg, S.L., Fletcher, T. and Mc Loughlin, M. (1996) J. Clin. Endocr. Metab. 67, 806-816.
6. Bratoeff, E., Ramírez, E., Murillo, E., Flores, G. and Cabeza, M. (1999) Curr. Med. Chem. 6, 1107-1123.
7. Russell, D.W. and Wilson, J.D. (1994) Annu. Rev. Biochem. 63, 25-61.
8. Morales-Alanis, H., Brienne, M.J., Jacques, J., Bouton, M.M., Nedelic, L., Torrelli, V. and Tournemine, C. (1985) J. Med. Chem. 28, 1796-1803.
9. Brooks, J.R., Harris, G.S. and Rassmusson, G.H. (1994) In: Sandler, M. and Smith, H.J., eds, Design of Enzyme Inhibitors as Drugs (Oxford University Press, Oxford) vol. 2, pp. 495-542.
10. Mc Connel, J., Wilson, J.D., George, F.G., Geller, J., Pappas, F. and Stoner, E. (1992) Clin. Endocrin. Metab. 74, 505-509.
11. Guess, H.A., Heyese, J.F. and Gormely, G.J. (1993) Prostate 22, 31-37.
12. Cabeza, M., Quiroz, A., Bratoeff, E., Murillo, E., Ramírez, E. and Flores, G. (1999) Chem. Pharm. Bull. 47, 1232-1236.
13. Cabeza, M., Heuze, I., Bratoeff, E., Murillo, E., Ramírez, E. and Lira, A. (2001) Chem. Pharm. Bull. 49, 1081-1084.
14. Cabeza, M., Quiroz, A., Bratoeff, E., Heuze, I., Ramírez, E. and Flores, E. (2002) Proc. West. Pharmacol. Soc. 45, 166-167.
15. Liang, T., Cascieri, M.A., Cheung, A.H., Reynolds, G.F. and Rasmusson, G.H. (1985) Endocrinology 117, 571-579.
16. Bradford, M.M. (1986) Anal. Biochem. 72, 248-254.
17. Hirosumi, J., Nakayama, O., Fagan, T., Sawada, K., Chida, N., Inami, M., Takahashi, S., Kojo, H., Notsu, Y. and Okuhara, M. (1995) J. Steroid Biochem. Molec. Biol. 52, 357-363.
18. Scatchard, G. (1949) Ann. NY Acad. Sci. 52, 660-666.
19. Chen, Y.C. and Prusoff, W.H. (1973) Biochem. Pharmacol. 22, 3099-3108.
20. Gormeley, G.J., Stoner, E., Bruskewiz, R.C., Imperato-McGinley, J., Walsh, P.C., McConnel, J.D., Andriole, G.L., Geller, J., Bracken, B., Tenover, J.S., Baughan, E.D., Pappas, F., Taylor, A. and Binkowitz, B. (1992) N. Engl. J. Med. 327, 1185-1191, Ng. Group FS.
21. Thigpen, A.E., Cala, K.M. and Russell, D.W. (1993) J. Biol. Chem. 268, 404-417, 412.
22. Berman, D.M. and Russell, D.W. (1993) Proc. Nat. Acad. Sci. USA 90, 9359-9361.