Stereoselective synthesis of the two major metabolites of spironolactone, 3α- and 3β-hydroxy-7α-methylthio-17α-pregn-4-ene-21,17-carbolactone

Steroids

Volumn 72, Issue 6-7, 2007, Pages 569-572

  Li, Guo ^a   Zhang, Yan ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

Metabolites; Spironolactone; Stereoselective synthesis

Indexed keywords

3ALPHA HYDROXY 7ALPHA METHYLTHIO 17ALPHA PREGN 4 ENE 21,17 CARBOLACTONE; 3BETA HYDROXY 7ALPHA METHYLTHIO 17ALPHA PREGN 4 ENE 21,17 CARBOLACTONE; REAGENT; SPIRONOLACTONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; METABOLITE; REDUCTION; STEREOCHEMISTRY;

MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPIRONOLACTONE; STEREOISOMERISM;

EID: 34248509094     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2007.03.011     Document Type: Article

References (26)

1. Wolf R.L., Mendlowitz M., and Roboz J. Treatment of hypertension with spironolactone: double-blind study. JAMA 198 (1966) 1143-1149
2. Jeunemaitre X., Chatellier G., and Kreft-Jais C. Efficacy and tolerance of spironolactone in essential hypertension. Am J Cardiol 60 (1987) 820-825
3. Smith A.G.E. Spironolactone in the long-term management of patients with congestive heart failure. Curr Med Res Opin 7 (1980) 131-136
4. Ikram H., Webster M.W.I., Nicholls M.G., Lewis G.R.J., Richards A.M., and Croziec I.G. Combined spironolactone and converting-enzyme inhibitor therapy for refractory heart failure. Aust N Z Med 16 (1986) 61-63
5. Huffman D.H., Kampmann J.P., Hignite C.E., and Azarnoff D.L. Gynecomastia induced in normal males by spironolactone. Clin Pharmacol Ther 24 (1978) 465-473
6. Shapiro G., and Evron S. A novel use of spironolactone: treatment of hirsutism. J Clin Endocrinol Metab 51 (1980) 429-432
7. Cumming D.C., Yang J.C., Rebar R.W., and Yen S.C.C. Treatment of hirsutism with spironolactone. JAMA 247 (1982) 1295-1298
8. Los L.E., Pitzenberger S.M., Ramjit H.G., Cod Dington A.B., and Colby H.D. Hepatic metabolism of spironolactone: production of 3-hydroxy-methylthio metabolites. Drug Metab Dispos 22 (1994) 903-908
9. Ricardo G., Lucia N., Ricardo C., Miguel V., Juan T., and Eva D. Spironolactone and its main metabolite canrenoic acid block hKv1.5, Kv4. 3 and Kv7. 1 + minK channels. Br J Pharmacol 146 (2005) 146-161
10. Karim A., and Brown E.A. Isolation and identification of novel sulfur-containing metabolites of spironolactone. Steroids 20 (1972) 41-62
11. Luche J.-L., Rodrigues-Hahn L., and Crabbe P. Reduction of natural enones in the presence of cerium trichloride. JCS Chem Comm (1978) 601-602
12. Cui J.G., Lin C.W., Zeng L.M., and Su J.Y. Synthesis of polyhydroysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3β,6α-diol. Steroids 67 (2002) 1015-1019
13. 4-steroids with rhodium-phosphite catalysts. Tetrahedron: Asymmetry 12 (2001) 1083-1087
14. Nahar L., and Turner A.B. Synthesis of 3β, 6α-dihydroxy-5α-cholan-23-one. Tetrahedron 59 (2003) 8623-8628
15. Bystroem S.E., Boerje A., and Akermark B. Selective reduction of steroid 3- and 17-ketones using LiAlH4 activated template polymers. J Am Chem Soc 115 (1993) 2081-2083
16. De Bruyn M., Coman S., Bota R., Parvulescu V.I., De Vos D.E., and Jacobs P.A. Chemoselective reduction of complex α,β-unsaturated ketones to allylic alcohols over Ir-metal particles on β zeolites. Angew Chem 42 (2003) 5333-5336
17. Loughhead D.G. Preparation and acid-catalyzed rearrangement of a C-17 isopropylidene and a C-17 isopropenyl sterol. J Org Chem 50 (1985) 3931-3934
18. Gondos G., and Orr J.C. Stereoselective and regioselective reduction of steroid ketones by potassium tri(R,S-s-butyl)borohydride. J Chem Soc Chem Commun (1982) 1239-1240
19. Wiebe J.P., Deline C., and Buckingham K.D. Synthesis of the allylic gonadal steroids, 3α-hydroxy-4-pregnen-20-one and 3α-hydroxy-4-androsten-17-one, and of 3α-hydroxy-5α-pregnan-20-one. Steroids 45 (1985) 39-51
20. Gondos G., McGirr L.G., Jablonski C.R., Snedden W., and Orr J.C. The reduction of steroid 2α-fluoro-4-en-3-ones. J Org Chem 53 (1988) 3057-3059
21. Gondos G., and Orr J.C. Reduction of steroid 17-ketones by enantiomeric chiral reducing agents. J Chem Soc Chem Commun (1982) 1238-1239
22. Wiebe J.P., Dave V., and Stothers J.B. Synthesis and characteristics of allylic 4-pregnene-3,20-diols ound in gonadal and breast tissues. Steroids 47 (1986) 249-259
23. A receptor activity of 6-oxa-analogs of neurosteroids. Steroids 65 (2000) 349-356
24. A receptor activity of a 6,19-oxido analogue of pregnanolone. Bioorg Med Chem Lett 13 (2003) 343-346
25. Brown H.C., and Krishnamurthy S. Lithium tri-sec-butylborohydride. A new reagent for the reduction of cyclic and bicyclic ketones with super stereoselectivity. A remarkably simple and practical procedure for the conversion of ketones to alcohols in exceptionally high stereochemical purity. J Am Chem Soc 94 (1972) 7159-7161
26. Hutchins R.O. Conformational control. An important factor in the stereoselective reduction of ketones by bulky hydride reagents. J Org Chem 42 (1977) 920-922