C(10)-C(19) bond cleavage reaction of 19-oxygenated androst-4-ene-3,6-dione steroids under various conditions

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 8, 2004, Pages 983-985

  Nagaoka, Masao ^a   Numazawa, Mitsuteru ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

19 oxygenated steroid; 6 oxoandrostenedione; Aromatase inhibitor; C(10) C(19) bond cleavage

Indexed keywords

19 HYDROXY 4 ENE 3,6,17 TRIONE; 19 OXOANDROST 4 ENE 3,6,17 TRIONE; 3 METHYL ETHER; 4 METHYL 6 OXOESTRONE; 6 OXOESTRONE; ACID; BASE; CARBON; DELTA6 ESTRONE; DELTA6 ESTRONE 3 METHYL ETHER; ETHER DERIVATIVE; HYDROCHLORIC ACID; STEROID; UNCLASSIFIED DRUG; 19 OXO DELTA(4) ANDROSTENE 3,17 DIONE; 19-OXO-DELTA(4) ANDROSTENE-3,17-DIONE; ALDEHYDE; ANDROSTENEDIONE; AROMATASE; DRUG DERIVATIVE; ESTRONE; HYDROXIDE; POTASSIUM DERIVATIVE; POTASSIUM HYDROXIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; DRUG STRUCTURE; STRUCTURE ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM;

ALDEHYDES; ANDROSTENEDIONE; AROMATASE; CARBON; ESTRONE; HYDROCHLORIC ACID; HYDROXIDES; MOLECULAR STRUCTURE; POTASSIUM COMPOUNDS;

EID: 16644378819     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.52.983     Document Type: Article

References (17)

1. For a review see: Covey D. F., "Steroid Biosynthesis Inhibitors: Pharmaceutical and Agrochemical Aspects," ed. by Berg D., Plemel M., Ellis Horwood Ltd., Chichester, 1988, pp. 534-571.
2. Schwarzel W. C., Kruggel W., Brodie H. J., Endocrinology, 92, 866-880 (1973).
3. Covey D. F., Hood W. F., Endocrinology, 108, 1597-1599 (1981).
4. Numazawa M., Tsuji M., Mutsumi A., J. Steroid Biochem., 28, 337-344 (1987).
5. Numazawa M., Midzuhasi K., Nagaoka M., Biochem. Pharmacol., 47, 717-726 (1994).
6. Numazawa M., Mutsumi A., Tachibana M., Biochem. Pharmacol., 52, 1253-1259 (1996).
7. Numazawa M., Sugiyama T., Nagaoka M., Biol. Pharm. Bull., 21, 289-292 (1998).
8. Numazawa M., Tachibana M., Steroids, 58, 423-428 (1993).
9. Hagiwara H., Noguchi S., Nishikawa M., Chem. Pharm. Bull., 8, 84-85 (1960).
10. Barber G. W., Ehrenstein M., J. Org. Chem., 20, 1253-1259 (1955).
11. Numazawa M., Oshibe M., Biol. Pharm. Bull., 18, 782-784 (1995).
12. Osawa Y., Shibata K., Rohrer D., Weeks C., Duax W. L., J. Am. Chem. Soc., 97, 4400-4402 (1975).
13. Numazawa M., Sohtome S., Nagaoka M., Chem. Pharm. Bull., 52, 722-726 (2004).
14. Numazawa M., Oshibe M., Matsuzaki H., Steroids, 58, 423-428 (1993).
15. Yoshizawa I., Kamiya E., Itoh S., Yakugaku Zasshi, 101, 285-290 (1981).
16. Kirk P. N., Hartshorn M. P., "Steroid Reaction Mechanisms," Chap. 5, Elsevier Publishing Company, Amsterdam, 1968, pp. 277-290.
17. Kitagawa I., Nakanishi T., Morii Y., Yoshioka I., Chem. Pharm. Bull., 25, 2343-2349 (1977).