Synthesis and pharmacological evaluation of new 16-methyl pregnane derivatives

Chemical and Pharmaceutical Bulletin

Volumn 50, Issue 1, 2002, Pages 15-20

  Ramirez, Elena ^a   Cabeza, Marisa ^b   Heuze, Ivonne ^b   Gutiérrez, Edgar ^b   Bratoeff, Eugene ^a   Membrillo, Marisol ^a   Lira, Alfonso ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b Metropolitan University   (Mexico)

Author keywords

5 reduction; C 16 substituent; Flank organ; Seminal vesicle; Testosterone conversion

Indexed keywords

16BETA METHYL 17ALPHA VALEROPREGNA 1,4,6 TRIENE 3,20 DIONE; 16BETA METHYL 17ALPHA VALEROPREGNA 4,6 DIENE 3,20 DIONE; 17BETA HYDROXY 16ALPHA METHYLPREGNA 1,4,6 TRIENE 3,20 DIONE; 6 BROMO 16BETA METHYL 17ALPHA VALEROPREGNA 4,6 DIENE 3,20 DIONE; ANDROSTANOLONE; EPOXY 16BETA METHYL 17ALPHA VALEROPREGNA 4 ENE 3,20 DIONE; FINASTERIDE; PREGNANE DERIVATIVE; STEROID 5ALPHA REDUCTASE INHIBITOR; TESTOSTERONE; UNCLASSIFIED DRUG; ANTIANDROGEN; ENZYME INHIBITOR; STEROID 5ALPHA REDUCTASE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG INHIBITION; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; GONADECTOMY; HAMSTER; IN VITRO STUDY; MALE; NONHUMAN; ORGAN; SEMINAL VESICLE; TESTOSTERONE METABOLISM; ANIMAL; DRUG ANTAGONISM; DRUG EFFECT; METABOLISM; ORCHIECTOMY; ORGAN SIZE; SYNTHESIS;

ANDROGEN ANTAGONISTS; ANIMALS; CRICETINAE; ENZYME INHIBITORS; MALE; ORCHIECTOMY; ORGAN SIZE; PREGNANES; SEMINAL VESICLES; TESTOSTERONE; TESTOSTERONE 5-ALPHA-REDUCTASE;

EID: 0036365198     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.50.15     Document Type: Article

References (28)

1. Krieg M., Tunn S., "Testosterone Action, Deficiency, Substitution," ed. by Nieschlag, Behre H. M., Springer Verlag, Bcrlin/Heidelberg/New York/London/Paris/Tokyo/Hong Kong/Barcelona, 1990, pp. 219-244.
2. Krieg M., Weiser H., Tunn S., J. Steroid Biochem. Molec. Biol., 53, 395-400 (1995).
3. Tunn S., Hochstrate H., Grumvald I., Flucher ST. H., Krieg M., J. Clin. Endocrinol. Metab., 67, 979-985 (1988).
4. Liang T., Cascieri M., Cheung A., Reynolds G., Rasmusson G., Endocrinology, 117, 571-579 (1985).
5. Gormley 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., Binkowitz B., Ng J., Group F. S., N. Engl. J. Med., 327, 1185-1191 (1992).
6. Levy M. A., Brandt M., Heys R., Holt D. A., Metclaff B. W., Biochemistry, 29, 2815-2824 (1990).
7. Horton R., Kato M., Sherino R., Steroids, 10, 245-249 (1967).
8. Clark C., Nowell N., Steroids, 34, 139-149 (1979).
9. Giudici D., Briatico G., Cominato C., J. Ster. Biochem. Mol. Biol., 58, 299-305 (1996).
10. Weisser H., Tunn S., Debus M., Krieg M., Steroids, 59, 616-620 (1994).
11. Andersson S., Berman D. M., Jenkins E. P., Russel D. W., Nature (London), 54, 159-161 (1991).
12. Thigpen A., Russel D. W., J. Biol. Chem., 267, 8577-8583 (1992).
13. Cabeza M., Gutierrez E., Miranda R., Heuze I., Bratoeff E., Flores G., Ramirez E., Steroids, 64, 413-421 (1999).
14. Takayasu S., Adachi K., Endocrinology, 90, 73-80 (1972).
15. Hisoaka H., Ideta R., Seki T., Adachi K., Arch. Dermatol. Res., 283, 269-273 (1991).
16. Vermorken A. J. M., Goos C. M. A., Wirtz P., British J. Dermatol., 106, 99-101 (1982).
17. Cabeza M., Quiroz A., Bratoeff E., Murillo E., Ramirez E., Flores G., Chem. Pharm. Bull., 47, 1232-1236 (1999).
18. Chen C., Puy L. A., Semard S. M., J., Li X., Singh S., Labrie F., J. Invest. Dermatol., 105, 678-682 (1995).
19. Bruchowski N., Wilson J. D., J. Biol. Chem., 243, 2012-2021 (1968).
20. Kaufman K. D., Olsen E. A., Whiting D., Savin R., Bergfeld W., Price V. H., Van Neste D., Roberts J. L., Shapiro J., Binkowitz B., Gormley G. J., J. Am. Acad. Dermatol., 39, 578-589 (1998).
21. Bayne E. K, Flanagan J., Einstein M., Ayala J., Chang B., Azzolina B., Whiting D. A., Mumford R. A., Thiboutot D., Singer I. L., Harris G., British J. Dermatol., 141, 481-491 (1999).
22. Kumar N., Didolkar A. K., Monder C., Bardin W. C., Sundram M., Endocrinology, 130, 3677-3683 (1993).
23. Cabeza M., Heuze I., Bratoeff E., Ramirez E., Martinez R., Chem. Pharm. Bull., 49, 525-530 (2001).
24. Bratoeff E., Herrera H., Ramirez E., Solorzano K., Murillo E., Quiroz A., Cabeza M., Chem. Pharm. Bull., 48, 1249-1255 (2000).
25. Bratoeff E., Ramirez E., Murillo E., Flores G., Cabeza M., Curr. Med. Chem., 6, 1107-1123 (1999).
26. Bratoeff E., Rubio M., Ramirez E., Garcia J., Ramirez G., Chemistry Today, 16, 33-35 (1998).
27. Petrow V., Yueh-sha Wang, Lack L., Steroids, 38, 121-140 (1981).
28. Bradford M. M., Anal. Biochem., 72, 248-254 (1986).