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Volumn 69, Issue 3, 2004, Pages 161-171

Synthesis of [19-2H3]-analogs of dehydroepiandrosterone and pregnenolone and their sulfates

Author keywords

Deuterium; NMR spectra; Steroid; Synthesis

Indexed keywords

17,17 ETHYLENEDIOXY 3BETA DIMETHOXY 19 ANDROST 5 ENE; 17,17 ETHYLENEDIOXY 3BETA DIMETHOXYANDROST 5 EN 19 OATE; 19 HYDROXY 6BETA METHOXY 3ALPHA,5 CYCLO 5ALPHA PREGNAN 20 ONE; 19 HYDROXY 6BETA METHOXY 3ALPHA,5 CYCLO 5ALPHA,17ALPHA PREGNAN 20 ONE; 20 OXOPREGN 5 ENE 3BETA,19 DIYL DIACETATE; 20,20 ETHYLENEDIOXY 3BETA DIMETHOXY 19 PREGN 5 EN 19 OL; 20,20 ETHYLENEDIOXY 3BETA DIMETHOXY 19 PREGN 5 ENE; 3BETA HYDROXY 19 PREGN 5 EN 20 ONE; 3BETA HYDROXY 20 OXOPREGN 5 EN 19 YL ACETATE; ALUMINUM; DEUTERIUM OXIDE; HYDROXYL GROUP; IODIDE; LITHIUM; MESYLIC ACID; METHYL 17,17 ETHYLENEDIOXY 3BETA DIMETHOXYANDROST 5 EN 19 OATE; METHYL 20,20 ETHYLENEDIOXY 3BETA DIMETHOXYPREGN 5 EN 19 OATE; METHYL 3BETA HYDROXY 17 OXOANDROST 5 EN 19 OATE; METHYL 3BETA HYDROXY 20 OXOPREGN 5 EN 20 ONE; PRASTERONE; PREGNENOLONE DERIVATIVE; PREGNENOLONE SULFATE; PYRIDINIUM 17 OXO 19 ANDROST 5 EN 3BETA YL SULFATE; PYRIDINIUM 20 OXO 19 PREGN 5 EN 3BETA YL SULFATE; PYRIDINIUM DERIVATIVE; SODIUM 17 OXO 19 ANDROST 5 EN 3BETA YL SULFATE; SODIUM 20 OXO 19 PREGN 5 EN 3BETA YL SULFATE; SULFATE; UNCLASSIFIED DRUG; ZINC; 5ALPHA ANDROSTANE; ANDROSTANE DERIVATIVE; DEUTERIUM; DRUG DERIVATIVE; ELTANOLONE; PREGNENOLONE;

EID: 1842789886     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2003.11.002     Document Type: Article
Times cited : (7)

References (23)
  • 1
    • 0035666911 scopus 로고    scopus 로고
    • Role of pregnenolone, dehydroepiandrosterone and their sulfate esters on learning and memory in cognitive aging
    • Valleé M., Mayo W., Le Moal M. Role of pregnenolone, dehydroepiandrosterone and their sulfate esters on learning and memory in cognitive aging. Brain Res. Rev. 37:2001;301-312.
    • (2001) Brain Res. Rev. , vol.37 , pp. 301-312
    • Valleé, M.1    Mayo, W.2    Le Moal, M.3
  • 2
    • 0026542895 scopus 로고
    • Memory-enhancing effects in male mice of pregnenolone and steroids metabolically derived from it
    • Flood J.F., Morley J.E., Roberts E. Memory-enhancing effects in male mice of pregnenolone and steroids metabolically derived from it. Proc. Natl. Acad. Sci. U.S.A. 89:1992;1567-1571.
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 1567-1571
    • Flood, J.F.1    Morley, J.E.2    Roberts, E.3
  • 3
    • 0028853687 scopus 로고
    • Pregnenolone sulfate enhances post-training memory processes when injected in very low doses into limbic system structures: The amygdala is by far the most sensitive
    • Flood J.F., Morley J.E., Roberts E. Pregnenolone sulfate enhances post-training memory processes when injected in very low doses into limbic system structures: the amygdala is by far the most sensitive. Proc. Natl. Acad. Sci. U.S.A. 92:1995;10806-10810.
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 10806-10810
    • Flood, J.F.1    Morley, J.E.2    Roberts, E.3
  • 4
    • 0032209377 scopus 로고    scopus 로고
    • Integrated medicine and the prevention and reversal of memory loss
    • Khalsa D.S. Integrated medicine and the prevention and reversal of memory loss. Altern. Ther. Health Med. 4:1998;38-43.
    • (1998) Altern. Ther. Health Med. , vol.4 , pp. 38-43
    • Khalsa, D.S.1
  • 5
    • 0034628965 scopus 로고    scopus 로고
    • Prolonged intracerebroventricular infusion of neurosteroids affects cognitive performances in the mouse
    • Ladurelle N., Eychenne B., Denton D., Blair-West J., Schumacher M., Robel P., Baulieu E. Prolonged intracerebroventricular infusion of neurosteroids affects cognitive performances in the mouse. Brain Res. 858:2000;371-379.
    • (2000) Brain Res. , vol.858 , pp. 371-379
    • Ladurelle, N.1    Eychenne, B.2    Denton, D.3    Blair-West, J.4    Schumacher, M.5    Robel, P.6    Baulieu, E.7
  • 6
    • 0034739778 scopus 로고    scopus 로고
    • Neuroactive steroids, their precursors, and polar conjugates during parturition and postpartum in maternal and umbilical blood. 1. Identification and simultaneous determination of pregnanolone isomers
    • Hill M., Pařízek A., Bičíková M., Havlíková H., Klak J., Fajt T.et al. Neuroactive steroids, their precursors, and polar conjugates during parturition and postpartum in maternal and umbilical blood. 1. Identification and simultaneous determination of pregnanolone isomers. J. Steroid. Biochem. Mol. Biol. 75:2000;237-244.
    • (2000) J. Steroid. Biochem. Mol. Biol. , vol.75 , pp. 237-244
    • Hill, M.1    Pařízek, A.2    Bičíková, M.3    Havlíková, H.4    Klak, J.5    Fajt, T.6
  • 7
    • 1842706298 scopus 로고
    • C(19)-substituted hormone analogues
    • (London)
    • Halpern O, Villoti R, Bowers A. C(19)-substituted hormone analogues. Chem Ind (London) 1963;39-40.
    • (1963) Chem. Ind. , pp. 39-40
    • Halpern, O.1    Villoti, R.2    Bowers, A.3
  • 9
    • 0022625093 scopus 로고
    • Convenient preparative routes to 19-hydroxy, 19-oxo, 19-oic, and 19-nor-deoxycorticosterone
    • Terasawa T., Okada T. Convenient preparative routes to 19-hydroxy, 19-oxo, 19-oic, and 19-nor-deoxycorticosterone. Tetrahedron. 42:1986;537-545.
    • (1986) Tetrahedron , vol.42 , pp. 537-545
    • Terasawa, T.1    Okada, T.2
  • 10
    • 26544443734 scopus 로고
    • 6β-Alkoxy-10β-carboxy-3α,5-cyclo steroids. Neth Appl 6,610,073 (January 20, 1967);
    • Sankyo Co. Ltd. (assignee). 6β-Alkoxy-10β-carboxy-3α,5- cyclo steroids. Neth Appl 6,610,073 (January 20, 1967); Chem Abstr 1968;68:39949v.
    • (1968) Chem. Abstr. , vol.68
  • 13
    • 0014037446 scopus 로고
    • Steroid series. XVI. The preparation of 3α,5α-cyclo-6β, 19-oxidosteroids and its conversion to 19-oxygenated steroid derivatives
    • Tanabe T., Takasaki R., Sakai K., Hayashi R., Morisawa Y., Hashimoto T. Steroid series. XVI. The preparation of 3α,5α-cyclo-6β,19- oxidosteroids and its conversion to 19-oxygenated steroid derivatives. Chem. Pharm. Bull. 15:1967;15-27.
    • (1967) Chem. Pharm. Bull. , vol.15 , pp. 15-27
    • Tanabe, T.1    Takasaki, R.2    Sakai, K.3    Hayashi, R.4    Morisawa, Y.5    Hashimoto, T.6
  • 14
    • 26544434547 scopus 로고
    • 19-Oxygenated steroids. Br 994,747 (July 15, 1960);
    • Ciba Ltd. (assignee). 19-Oxygenated steroids. Br 994,747 (July 15, 1960); Chem Abstr 1965;63:13363b.
    • (1965) Chem. Abstr. , vol.63
  • 16
    • 1842656077 scopus 로고
    • The determination of sodium dehydroisoandrosterone sulfate in water or urine
    • Talbot N.B., Ryan J., Wolfe J.K. The determination of sodium dehydroisoandrosterone sulfate in water or urine. J. Biol. Chem. 148:1943;593-602.
    • (1943) J. Biol. Chem. , vol.148 , pp. 593-602
    • Talbot, N.B.1    Ryan, J.2    Wolfe, J.K.3
  • 17
    • 84960956958 scopus 로고
    • Salts of dehydroepiandrosterone sulfate
    • D'Alo F. Salts of dehydroepiandrosterone sulfate. Farmaco (Pavia) Ed Sci 1956;11:477-83; Chem Abstr 1959;53:11445b.
    • (1956) Farmaco. (Pavia) Ed. Sci. , vol.11 , pp. 477-483
    • D'Alo, F.1
  • 18
    • 84960956958 scopus 로고
    • D'Alo F. Salts of dehydroepiandrosterone sulfate. Farmaco (Pavia) Ed Sci 1956;11:477-83; Chem Abstr 1959;53:11445b.
    • (1959) Chem. Abstr. , vol.53
  • 20
    • 0015168665 scopus 로고
    • Steroid conjugates. Part IV. The influence of the cation in borohydride reduction of ketol sulphates
    • Baxendale D, Kirk DN, Rajagopalan MS, Turner AB. Steroid conjugates. Part IV. The influence of the cation in borohydride reduction of ketol sulphates. J Chem Soc (C) 1971;2563-6.
    • (1971) J. Chem. Soc. (C) , pp. 2563-2566
    • Baxendale, D.1    Kirk, D.N.2    Rajagopalan, M.S.3    Turner, A.B.4
  • 21
    • 1842656079 scopus 로고
    • 18-Substituted steroids. Part 12. Synthesis of aldosterone 21-sulphate, and an improved general procedure for preparing steroid sulphates
    • Kirk DN, Rajagopalan MS. 18-Substituted steroids. Part 12. Synthesis of aldosterone 21-sulphate, and an improved general procedure for preparing steroid sulphates. J Chem Soc, Perkin Trans 1 1987;1339-42.
    • (1987) J. Chem. Soc., Perkin. Trans. 1 , pp. 1339-1342
    • Kirk, D.N.1    Rajagopalan, M.S.2
  • 22
    • 0344903525 scopus 로고
    • Steroid conjugates. Part III. Syntheses of 19-oxygenated dehydro-epi-androsterone sulphates
    • Rajagopalan MS, Smith DSH, Turner AB. Steroid conjugates. Part III. Syntheses of 19-oxygenated dehydro-epi-androsterone sulphates. J Chem Soc (C) 1971;646-50.
    • (1971) J. Chem. Soc. (C) , pp. 646-650
    • Rajagopalan, M.S.1    Smith, D.S.H.2    Turner, A.B.3
  • 23
    • 0042149767 scopus 로고
    • Construction of the side-chain in 14β-androst-5-ene derivatives. Preparation of 14β-pregnenolone
    • Černý I., Buděšínský M., Drašar P., Pouzar V. Construction of the side-chain in 14β-androst-5-ene derivatives. Preparation of 14β-pregnenolone. Collect. Czech. Chem. Commun. 59:1994;2691-2704.
    • (1994) Collect. Czech. Chem. Commun. , vol.59 , pp. 2691-2704
    • Černý, I.1    Buděšínský, M.2    Drašar, P.3    Pouzar, V.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.