Preparation of (5α,13α)-D-azasteroids as key precursors of a new family of potential GABAA receptor modulators

Steroids

Volumn 68, Issue 7-8, 2003, Pages 677-683

  Wang, Cunde ^a   Wang, Shaozhong ^a   Xu, Yingju ^a   Hu, Yuefei ^a,b   Hu, Hongwen ^a  

^a NANJING UNIVERSITY   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

(5 ,13 ) D Azasteroids; GABAA receptor modulators; Synthesis

Indexed keywords

3 HYDROXY 17 AZA DEXTRO HOMOANDROSTANE; 3 HYDROXY 17ALPHA AZA DEXTRO HOMOANDROSTANE; 3 HYDROXY 17ALPHA DEXTRO HOMOANDROSTANE; 3 HYDROXYANDROSTAN 17 ONE; 4 AMINOBUTYRIC ACID A RECEPTOR; STEROID; UNCLASSIFIED DRUG;

ARTICLE; COMMERCIAL PHENOMENA; DRUG DESIGN; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0042737828     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(03)00099-0     Document Type: Article

References (18)

1. Phillipps GH. Structure-activity relationships in steroidal anesthetic. In: Halsey MJ, Millar RA, Sutton JA, editors. Molecular mechanisms in general anaesthesia. New York: Churchill Livingston; 1974. p. 32-47.
2. Lambert JJ, Belelli D, Pistis M, Hill-Venning C, Peters JA. In: Enna SJ, Bowery NG, editors. GABA receptors. 2nd ed. Totowa: Humana Press; 1997. p. 121-56.
3. (a) Covey D.F., Han M., Kumar A.S., De la Cruz M.A.M., Meadows E.S., Hu Y.et al. Nerosteroid analogues. 8. Structure-activity studies of N-acylated 17a-aza-D-homosteroid analogues of the anesthetic steroids (3α,5α)- and (3α,5β)-3-hydroxypregnan-20-one. J. Med. Chem. 43:2000;3201-3204 (b) Jiang X., Wang J., Hu J., Ge Z., Hu Y., Hu H.et al. Synthesis of (5α)-17-azaandrostan-3-ols and (5α)-17-aza-D-homoandrostan-3-ols and their N-acylated derivatives. Steroids. 66:2001;655-662.
4. (a) Covey D.F., Han M., Kumar A.S., De la Cruz M.A.M., Meadows E.S., Hu Y.et al. Nerosteroid analogues. 8. Structure-activity studies of N-acylated 17a-aza-D-homosteroid analogues of the anesthetic steroids (3α,5α)- and (3α,5β)-3-hydroxypregnan-20-one. J. Med. Chem. 43:2000;3201-3204 (b) Jiang X., Wang J., Hu J., Ge Z., Hu Y., Hu H.et al. Synthesis of (5α)-17-azaandrostan-3-ols and (5α)-17-aza-D-homoandrostan-3-ols and their N-acylated derivatives. Steroids. 66:2001;655-662.
5. 2 promoted cyclization and dehydroxylation. J. Org. Chem. 65:2000;3555-3557.
6. Schöneeker B., Lange C.X., Kötteritzsch M., Gunther W., Weston J., Anders E.et al. Conformational design for 13α-steroids. J. Org. Chem. 65:2000;5487-5497.
7. 18. J Chem Soc 1957:2698-706. (c) Johnson W.S., Shulman S., Williamson K.L., Pappo R. Production of a fused-ring system by an intramolecular Michael condensation. J. Org. Chem. 27:1962;2015-2108 (d) Ohloff G., Maurer B., Winter B., Giersch W. Structural and configurational dependence of the sensory process in steroids. Helv. Chim. Acta. 66:1983;192-217.
8. 18. J Chem Soc 1957:2698-706. (c) Johnson W.S., Shulman S., Williamson K.L., Pappo R. Production of a fused-ring system by an intramolecular Michael condensation. J. Org. Chem. 27:1962;2015-2108 (d) Ohloff G., Maurer B., Winter B., Giersch W. Structural and configurational dependence of the sensory process in steroids. Helv. Chim. Acta. 66:1983;192-217.
9. 18. J Chem Soc 1957:2698-706. (c) Johnson W.S., Shulman S., Williamson K.L., Pappo R. Production of a fused-ring system by an intramolecular Michael condensation. J. Org. Chem. 27:1962;2015-2108 (d) Ohloff G., Maurer B., Winter B., Giersch W. Structural and configurational dependence of the sensory process in steroids. Helv. Chim. Acta. 66:1983;192-217.
10. 18. J Chem Soc 1957:2698-706. (c) Johnson W.S., Shulman S., Williamson K.L., Pappo R. Production of a fused-ring system by an intramolecular Michael condensation. J. Org. Chem. 27:1962;2015-2108 (d) Ohloff G., Maurer B., Winter B., Giersch W. Structural and configurational dependence of the sensory process in steroids. Helv. Chim. Acta. 66:1983;192-217.
11. A receptors. J. Med. Chem. 43:2000;4118-4125.
12. A receptors. J. Med. Chem. 43:2000;4118-4125.
13. A receptors. J. Med. Chem. 43:2000;4118-4125.
14. Yaremenko FG, Khvat AV. A new one-pot synthesis of 17-oxo-13α -steroids of the androstane series from their 13β-analogues. Mendeleev Commun 1994:187-8 [Chem Abstr 1995;122:214318w].
15. Chapman J.C., Pinhey J.T. Route to 18-nor- and 19-norsteroids. Aust. J. Chem. 27:1974;2421-2430.
16. Huffman M.N., Lott M.H. 16-Substituted steroids. IX. Androstan-3β -ol-16-one. J. Biol. Chem. 207:1954;431-437.
17. Jones SERH, Meakins GD, Tuba KZ. Studies in the steroid group. Part LXXIX. Preparation of 2-aza-3-oxo, 3-aza-2-oxo-, 16-aza-17-oxo- and 17-aza-16-oxo-5α-androstane, and of 3-aza-2-oxo-5α-cholestane. J Chem Soc (C) 1969:1597-602.
18. Radlick P, Brown LR. A versatile modification of the Hofmann rearrangement. Synthesis 1974:290-2.