Synthesis of 19-oxygenated derivatives of the competitive inhibitor of aromatase, 5-androstene-4,17-dione

Steroids

Volumn 64, Issue 5, 1999, Pages 320-327

  Numazawa, Mitsuteru ^a   Yamada, Keiko ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

19 Hydroxy steroid; 19 Oxo steroid; Androst 5 ene 4,17 dione; Aromatase inhibitor; Gas chromatography mass spectrometry; Synthesis

Indexed keywords

ANDROST 5 ENE 4,17 DIONE; ANDROST 5 ENE 4,17,19 TRIONE; ANDROSTENEDIOL; AROMATASE INHIBITOR; OXOSTEROID; UNCLASSIFIED DRUG;

ARTICLE; COMPETITIVE INHIBITION; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INACTIVATION; ENZYME INHIBITION; GAS CHROMATOGRAPHY; HYDROLYSIS; MASS SPECTROMETRY; OXIDATION; REACTION ANALYSIS;

ANDROSTENEDIONE; AROMATASE INHIBITORS; BINDING, COMPETITIVE; CHEMISTRY, PHYSICAL; ENZYME INHIBITORS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ZINC;

EID: 0033014468     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(98)00113-5     Document Type: Article

References (32)

1. Thompson E.A. Jr, Siiteri P.K. The involvement of human placental microsomal cytochrome P-450 in aromatization. J Biol Chem. 249:1974;5373-5378.
2. Kellis J. Jr, Vickery L.E. Purification and characterization of human placental aromatase cytochrome P-450. J Biol Chem. 262:1987;4413-4420.
3. Yoshida N., Osawa Y. Purification of human placental aromatase cytochrome P-450 with monoclonal antibody and its characterization. Biochemistry. 30:1991;3003-3010.
4. Meyer A.S. Conversion of 19-hydroxy-4-androstene-3,17-dione to estrone by endocrine tissue. Biochim Biophys Acta. 17:1955;441-442.
5. Arigoni D., Battaglia R., Akhtar M., Smith T. Stereospecificity of oxidation at C-19 in oestrogen biosynthesis. J Chem Soc Chem Commun. 1975;185-187.
6. Osawa Y., Shibata K., Rohrer D., Weeks C., Duax W.L. Reassignment of the absolute configuration of 19-substituted 19-hydroxysteroids and stereomechanism of estrogen biosynthesis. J Am Chem Soc. 97:1975;4400-4402.
7. 1H]-3β-hydroxy-androst- 5-en-17-one by human placental aromatase . J Am Chem Soc. 108:1986;1847-1852.
8. Akhtar M., Calder M.R., Corina D.L., Wright J.N. Mechanistic studies on C-19 demethylation in oestrogen biosynthesis. Biochem J. 201:1982;569-580.
9. 2. J Chem Soc Chem Commun. 1976;854-856.
10. Bednarski P.J., Nelson S.D. Dissociation of 19-hydroxy-, 19-oxo-, and aromatizing activities in human placental microsomes through the use of suicide substrate to aromatase. J Steroid Biochem. 32:1989;309-316.
11. 18 steroids. Biochemistry. 7:1968;33-40.
12. 2H]-androgens into oestrogens by human placental aromatase. Biochem J. 268:1990;553-561.
13. Hervey H.A., Lipton A., Santen R.J. Aromatase New perspectives for breast cancer . Cancer Res. 42:1982;3261s-3269s. (suppl).
14. Henderson D. Aromatase inhibitors Their biochemistry and clinical potential . J Steroid Biochem. 27:1987;905-914.
15. Covey D.F. Aromatase inhibitors specific inhibitors of oestrogen biosynthesis . Berg D., Plemel M. Steroid biosynthesis inhibitors pharmaceutical and agrochemical aspects . 1988;534-571 Ellis Horwood Ltd, Chichester, England.
16. Banting L., Nicholls P.J., Shaw M.A., Smith H.J. Recent developments in aromatase inhibition as a potential treatment of estrogen-dependent breast cancer. Ellis G.P., West G.B. Progress in medicinal chemistry, Vol. 26. 1989;253-298 Elsevier Science Publishers, Amsterdam, The Netherlands.
17. Bossche H.V. Inhibitors of P-450-dependent steroid biosynthesis From research to medical treatment . J Steroid Biochem Mol Biol. 43:1992;1003-1021.
18. Brodie A.M.H., Santen R.J. Aromatase and its inhibitors in breast cancer treatment-overview and perspective. Breast Cancer Res Treat. 30:1994;1-6.
19. Schwarzel W.C., Kruggel W.G., Brodie H.J. Studies on the mechanism of estrogen biosynthesis. VIII. The development of inhibitors of the enzyme system in human placenta. Endocrinology. 92:1973;866-880.
20. Numazawa M., Mutsumi A., Tsuji M. 3β-Hydroxyandrost-4-en-6-one derivatives as aromatase inhibitors. Steroids. 54:1989;299-311.
21. Numazawa M., Tachibana M., Tateda Y. 4-Oxygenated androst-5-en-17-ones and their 7-oxo derivatives as aromatase inhibitors. J Steroid Biochem Mol Biol. 58:1996;431-438.
22. Numazawa M., Mutsumi A., Hoshi K., Tanaka Y. Androst-5-en-7-one A novel class of suicide substrate of aromatase . Biochem Biophys Res Commun. 186:1992;32-39.
23. Numazawa M., Mutsumi A., Tachibana M., Hoshi K. Synthesis of androst-5-en-7-ones and androsta-3,5-dien-7-ones and their related 7-deoxy analogs as conformational and catalytic probes for the active site of aromatase. J Med Chem. 37:1994;2198-2205.
24. Numazawa M., Tachibana M. Studies directed toward a mechanistic evaluation of aromatase inhibition by androst-5-ene-7,17-dione. Time-dependent inactivation by the 19-nor and 5β,6β-epoxy derivatives. Steroids. 62:1997;516-522.
25. 5-steroids at C-4. J Chem Soc Perkin Trans 1. 1977;2941-2944.
26. Numazawa M., Yamada K. Reaction of androst-5-en-17-one with hypobromous acid and its use for synthesis of 19-oxygenated 5-ene and 4-en-6-one steroids. Steroids. 63:1998;62-69.
27. Bagli J.F., Morand P.F., Gaudry R. Synthetic studies on C-19 oxygenated pregnanes. J Org Chem. 28:1963;1207-1217.
28. Numazawa M., Yoshimura A., Oshibe M. Enzymic aromatization of 6-alkyl-substituted androgens, potent competitive and mechanism-based inhibitors of aromatase. Biochem J. 329:1998;151-156.
29. Numazawa M., Tachibana M., Kamiza M. Competing pathway involved in allylic acetoxylation of androst-5-en-17-one, and oxidation of allylic alcohols with chromium oxides. Steroids. 60:1995;499-505.
30. Kocovsky P. Synthesis of 3,4-, 4,5- and 5,6-unsaturated 19-substituted cholestan derivatives and related epoxides. Collect Czech Chem Commun. 45:1980;3008-3022.
31. Kocovsky P. Synthesis of some unsaturated homo cholestane derivatives. Collect Czech Chem Commun. 48:1983;3597-3617.
32. Covey D.F., Hood W.F. Enzyme-generated intermediates derived from 4-androstene-3,6,17-trione and 1,4,6-androstatriene cause a time-dependent decrease in human placental aromatase activity. Endocrinology. 108:1981;1597-1599.