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Volumn 72, Issue 4, 2007, Pages 360-367

Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents

Author keywords

1,4,6 Androstatriene 3,17 dione; 1,4,6 Cholestatrien 3 one; Chemoselective reduction; Rigid cyclic , unsaturated carbonyl compound

Indexed keywords

1,4,6 CHOLESTATRIEN 3 ONE; 2,3 DICHLORO 5,6 DICYANO 1,4 BENZOQUINONE; 3 OXO 1,4,6 ANDROSTATRIEN 17BETA OL; 4,6 CHOLESTADIEN 3BETA OL; 9 BORABICYCLO[3.3.1]NONANE; ANDROSTA 1,4,6 TRIENE 3,17 DIONE; BENZOQUINONE; CHOLESTANE DERIVATIVE; CHOLESTEROL; LITHIUM TRIBUTYLBOROHYDRIDE; LITHIUM TRIETHYLBOROHYDRIDE; NONANE; PRASTERONE; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

EID: 33947387998     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2006.12.008     Document Type: Article
Times cited : (9)

References (29)
  • 1
    • 0016650440 scopus 로고
    • Formation of oestratrienes from 5,6-epoxyandrostan-7-ols
    • Baldwin D., and Hanson J.R. Formation of oestratrienes from 5,6-epoxyandrostan-7-ols. J Chem Soc Perkin Trans I (1975) 1941-1946
    • (1975) J Chem Soc Perkin Trans I , pp. 1941-1946
    • Baldwin, D.1    Hanson, J.R.2
  • 2
    • 0345735695 scopus 로고
    • Regioselective epoxidation by air of sterol esters bearing several double bond using a ruthenium porphyrin catalyst
    • Tavares M., Ramasseul R., and Marchon J.C. Regioselective epoxidation by air of sterol esters bearing several double bond using a ruthenium porphyrin catalyst. Catal Lett 4 2 (1990) 163-167
    • (1990) Catal Lett , vol.4 , Issue.2 , pp. 163-167
    • Tavares, M.1    Ramasseul, R.2    Marchon, J.C.3
  • 3
    • 0001260730 scopus 로고    scopus 로고
    • Selective epoxidation of olefins by perfluoro-cis-2,3-dialkyloxaziridines (1)
    • Arnone A., DesMarteau D.D., Novo B., Petrov V.A., Pregnolato M., and Resnati G. Selective epoxidation of olefins by perfluoro-cis-2,3-dialkyloxaziridines (1). J Org Chem 61 25 (1996) 8805-8810
    • (1996) J Org Chem , vol.61 , Issue.25 , pp. 8805-8810
    • Arnone, A.1    DesMarteau, D.D.2    Novo, B.3    Petrov, V.A.4    Pregnolato, M.5    Resnati, G.6
  • 4
    • 0034596790 scopus 로고    scopus 로고
    • 5-unsaturated steroids catalyzed by ketones
    • 5-unsaturated steroids catalyzed by ketones. Chemistry 6 19 (2000) 3517-3521
    • (2000) Chemistry , vol.6 , Issue.19 , pp. 3517-3521
    • Yang, D.1    Jiao, G.S.2
  • 5
    • 0010521593 scopus 로고
    • Lithium and potassium trialkylborohydrides. Reagents for direct reduction of α,β-unsaturated carbonyl compounds to synthetically versatile enolates anions
    • Fortunato J.M., and Ganem B. Lithium and potassium trialkylborohydrides. Reagents for direct reduction of α,β-unsaturated carbonyl compounds to synthetically versatile enolates anions. J Org Chem 41 12 (1976) 2194-2200
    • (1976) J Org Chem , vol.41 , Issue.12 , pp. 2194-2200
    • Fortunato, J.M.1    Ganem, B.2
  • 6
    • 0018079091 scopus 로고
    • Biological activity of some oxygenated steroids
    • Kandutsch A.A., Chen H.W., and Heiniger H.J. Biological activity of some oxygenated steroids. Science 201 4355 (1978) 498-501
    • (1978) Science , vol.201 , Issue.4355 , pp. 498-501
    • Kandutsch, A.A.1    Chen, H.W.2    Heiniger, H.J.3
  • 7
    • 0024430192 scopus 로고
    • Biological activities of oxysterols
    • Smith L.L., and Johnson B.H. Biological activities of oxysterols. Free Radic Biol Med 7 (1989) 285-332
    • (1989) Free Radic Biol Med , vol.7 , pp. 285-332
    • Smith, L.L.1    Johnson, B.H.2
  • 8
    • 0342316532 scopus 로고    scopus 로고
    • Oxysterols: modulators of cholesterol metabolism and other process
    • Schroepfer G.J. Oxysterols: modulators of cholesterol metabolism and other process. Physiol Rev 80 (2000) 361-554
    • (2000) Physiol Rev , vol.80 , pp. 361-554
    • Schroepfer, G.J.1
  • 10
    • 84984356462 scopus 로고
    • Structure of a new sterol from the such China sponge Dysidea fragilis
    • Zhong Y.I., Su J.Y., Zeng L.M., Shen W., and Wang Q.-W. Structure of a new sterol from the such China sponge Dysidea fragilis. Chin J Chem 11 6 (1993) 560-564
    • (1993) Chin J Chem , vol.11 , Issue.6 , pp. 560-564
    • Zhong, Y.I.1    Su, J.Y.2    Zeng, L.M.3    Shen, W.4    Wang, Q.-W.5
  • 11
    • 0028899472 scopus 로고
    • A new cytotoxic dihydroxysterol from the soft coral Alcyonium pqtagonicum
    • Zeng L.M., Li K.Q., Su J.Y., Hu X., and Schmitz F.J. A new cytotoxic dihydroxysterol from the soft coral Alcyonium pqtagonicum. J Nat Prod 58 2 (1995) 296-298
    • (1995) J Nat Prod , vol.58 , Issue.2 , pp. 296-298
    • Zeng, L.M.1    Li, K.Q.2    Su, J.Y.3    Hu, X.4    Schmitz, F.J.5
  • 12
    • 0035238766 scopus 로고    scopus 로고
    • Synthesis of polyhydroxysterols (1): synthesis of 24-methylene-cholest-4-en-3β,6β-diol, a cytotoxic natural hydroxylated sterol
    • Cui J.G., Zeng L.M., Su Z.Y., and Lu W.G. Synthesis of polyhydroxysterols (1): synthesis of 24-methylene-cholest-4-en-3β,6β-diol, a cytotoxic natural hydroxylated sterol. Steroids 66 (2001) 33-38
    • (2001) Steroids , vol.66 , pp. 33-38
    • Cui, J.G.1    Zeng, L.M.2    Su, Z.Y.3    Lu, W.G.4
  • 13
    • 0015714737 scopus 로고
    • Inhibition of sterol synthesis in cultured mouse cells by 7α-hydroxycholesterol, 7β-hydroxycholesterol, and 7-ketocholesterol
    • Kandutsch A.A., and Chen H.W. Inhibition of sterol synthesis in cultured mouse cells by 7α-hydroxycholesterol, 7β-hydroxycholesterol, and 7-ketocholesterol. J Biol Chem 248 (1973) 8408-8417
    • (1973) J Biol Chem , vol.248 , pp. 8408-8417
    • Kandutsch, A.A.1    Chen, H.W.2
  • 14
    • 0016683849 scopus 로고
    • Cholesterol, 7-ketocholesterol, and 25-hydroxycholesterol uptake studies and effect on 3-hydroxy-3-methylglutaryl coenzymes A reductase activity in human fibroblasts
    • Breslow J.L., Lothrop D.A., Spaulding D.R., and Kandutsch A.A. Cholesterol, 7-ketocholesterol, and 25-hydroxycholesterol uptake studies and effect on 3-hydroxy-3-methylglutaryl coenzymes A reductase activity in human fibroblasts. Biochim Biophys Acta 398 (1975) 10-17
    • (1975) Biochim Biophys Acta , vol.398 , pp. 10-17
    • Breslow, J.L.1    Lothrop, D.A.2    Spaulding, D.R.3    Kandutsch, A.A.4
  • 15
    • 0017284223 scopus 로고
    • Inhibition of 3-hydroxy-3-methylglutaryl coenzymes A reductase activity in heptoma tissue culture cells by pure cholesterol and several cholesterol derivatives. Evidence supporting two distinct mechanism
    • Bell J.J., Sargeant T.E., and Watson J.A. Inhibition of 3-hydroxy-3-methylglutaryl coenzymes A reductase activity in heptoma tissue culture cells by pure cholesterol and several cholesterol derivatives. Evidence supporting two distinct mechanism. J Biol Chem 251 (1976) 1745-1758
    • (1976) J Biol Chem , vol.251 , pp. 1745-1758
    • Bell, J.J.1    Sargeant, T.E.2    Watson, J.A.3
  • 17
    • 0029027469 scopus 로고
    • Occurrence of cytochrome P450c mRNA and dehydroepiandrosterone biosynthesis in the rat gastrointestinal tract
    • Dalla V.L., Couet J., Labrie Y., Simard J., Belvedere P., and Simontacchi C. Occurrence of cytochrome P450c mRNA and dehydroepiandrosterone biosynthesis in the rat gastrointestinal tract. Mol Cell Endocrinol 111 (1995) 83-92
    • (1995) Mol Cell Endocrinol , vol.111 , pp. 83-92
    • Dalla, V.L.1    Couet, J.2    Labrie, Y.3    Simard, J.4    Belvedere, P.5    Simontacchi, C.6
  • 18
    • 0026546421 scopus 로고
    • Mechanism of cell growth inhibition and cell cycle arrest in human colonic adenocarcinoma cells dehydroepiandresterone: role of isoprenoid biosynthesis
    • Schulz S., Klann R.C., Schonfeld S., and Nyce J.W. Mechanism of cell growth inhibition and cell cycle arrest in human colonic adenocarcinoma cells dehydroepiandresterone: role of isoprenoid biosynthesis. Cancer Res 52 (1992) 1372-1376
    • (1992) Cancer Res , vol.52 , pp. 1372-1376
    • Schulz, S.1    Klann, R.C.2    Schonfeld, S.3    Nyce, J.W.4
  • 19
    • 0030758923 scopus 로고    scopus 로고
    • Oxythiamine and dehydroepiandrosterone inhibit the nonoxidative synthesis of ribose and tumor cell proliferation in vitro and vivo
    • Boros L.G., Puigjancer J., Cascante M., Lee W.N., Brandes J.L., and Bassilian S. Oxythiamine and dehydroepiandrosterone inhibit the nonoxidative synthesis of ribose and tumor cell proliferation in vitro and vivo. Surgery 57 (1997) 4242-4248
    • (1997) Surgery , vol.57 , pp. 4242-4248
    • Boros, L.G.1    Puigjancer, J.2    Cascante, M.3    Lee, W.N.4    Brandes, J.L.5    Bassilian, S.6
  • 20
    • 0031000078 scopus 로고    scopus 로고
    • Dehydroepiandrosterone-sulfate inhibits pancreatic carcinoma cell proliferation in vitro and vivo
    • Melvin W.S., Boros L.G., Muscarella P., Brandes J.L., Johnson L.A., and Fischer W.E. Dehydroepiandrosterone-sulfate inhibits pancreatic carcinoma cell proliferation in vitro and vivo. Surgery 121 (1997) 392-397
    • (1997) Surgery , vol.121 , pp. 392-397
    • Melvin, W.S.1    Boros, L.G.2    Muscarella, P.3    Brandes, J.L.4    Johnson, L.A.5    Fischer, W.E.6
  • 21
    • 0008631779 scopus 로고    scopus 로고
    • Facile and stereoselective synthesis of non-racemic 3,3,3-trifluoroalanine
    • Marcello C., Natalia B., Pierfrancesco B., Alessandra V., and Matteo Z. Facile and stereoselective synthesis of non-racemic 3,3,3-trifluoroalanine. Molecules 5 (2000) 1251-1258
    • (2000) Molecules , vol.5 , pp. 1251-1258
    • Marcello, C.1    Natalia, B.2    Pierfrancesco, B.3    Alessandra, V.4    Matteo, Z.5
  • 22
    • 0001019011 scopus 로고
    • Borohydride reducing agent derived from anion-exchange resin: selective reduction of α,β-unsaturated carbonyl compounds
    • Sande A.R., Jagadale M.H., Mane R.B., and Salunkhe M.H. Borohydride reducing agent derived from anion-exchange resin: selective reduction of α,β-unsaturated carbonyl compounds. Tetrahedron Lett 25 (1984) 3501-3504
    • (1984) Tetrahedron Lett , vol.25 , pp. 3501-3504
    • Sande, A.R.1    Jagadale, M.H.2    Mane, R.B.3    Salunkhe, M.H.4
  • 23
    • 0037909495 scopus 로고
    • 9-Borabicyclo[3.3.1]nonane as a highly selective reducing agent for the facile conversion of α,β-unsaturated aldehydes and ketones to the corresponding allylic alcohols in the presence of other functional groups
    • Brown H.C., and Krishnamurthy S. 9-Borabicyclo[3.3.1]nonane as a highly selective reducing agent for the facile conversion of α,β-unsaturated aldehydes and ketones to the corresponding allylic alcohols in the presence of other functional groups. J Org Chem 40 (1975) 1864-1865
    • (1975) J Org Chem , vol.40 , pp. 1864-1865
    • Brown, H.C.1    Krishnamurthy, S.2
  • 24
    • 0037333698 scopus 로고    scopus 로고
    • Addition reactions at the 16(17) double bond of 3-methoxy-13α-estra-1,3,5(10),16-tetraene
    • Mernyak E., Schonecker B., Lange C., Kotteritzsch M., Gorls H., Wolflin J., et al. Addition reactions at the 16(17) double bond of 3-methoxy-13α-estra-1,3,5(10),16-tetraene. Steroids 68 3 (2003) 289-295
    • (2003) Steroids , vol.68 , Issue.3 , pp. 289-295
    • Mernyak, E.1    Schonecker, B.2    Lange, C.3    Kotteritzsch, M.4    Gorls, H.5    Wolflin, J.6
  • 25
    • 0005831044 scopus 로고    scopus 로고
    • Efficient hydrogenation of sterically hindered olefins with borane-methyl sulfide complex
    • Rathore R., Weigand U., and Kochi J.K. Efficient hydrogenation of sterically hindered olefins with borane-methyl sulfide complex. J Org Chem 61 (1996) 5246-5256
    • (1996) J Org Chem , vol.61 , pp. 5246-5256
    • Rathore, R.1    Weigand, U.2    Kochi, J.K.3
  • 26
    • 0039004402 scopus 로고    scopus 로고
    • Kinetics of the reduction of pinacolone by borane-dimethyl sulfide and catecholborane in THF
    • Eckhardt C., Jockel H., and Schmidt R. Kinetics of the reduction of pinacolone by borane-dimethyl sulfide and catecholborane in THF. J Chem Soc Perkin Trans 2 (1999) 2155-2162
    • (1999) J Chem Soc Perkin Trans , vol.2 , pp. 2155-2162
    • Eckhardt, C.1    Jockel, H.2    Schmidt, R.3
  • 27
    • 0000779851 scopus 로고
    • 5-steroids by reduction of 1α,2α-epoxy-4,6-dien-3-ones with lithium in ammonia
    • 5-steroids by reduction of 1α,2α-epoxy-4,6-dien-3-ones with lithium in ammonia. Helv Chim Acta 64 (1981) 1870-1892
    • (1981) Helv Chim Acta , vol.64 , pp. 1870-1892
    • Furst, A.1    Labler, L.2    Meier, W.3
  • 28
    • 15244348775 scopus 로고    scopus 로고
    • Epoxidation and reduction of cholesterol, 1,4,6-cholestatrien-3-one and 4,6-cholestadien-3β-ol
    • Ma E., Kim H., and Kim E. Epoxidation and reduction of cholesterol, 1,4,6-cholestatrien-3-one and 4,6-cholestadien-3β-ol. Steroids 70 (2005) 245-250
    • (2005) Steroids , vol.70 , pp. 245-250
    • Ma, E.1    Kim, H.2    Kim, E.3
  • 29
    • 33947432702 scopus 로고    scopus 로고
    • Epoxidation and reduction of DHEA, 1,4,6-androstatrien-3-one and 4,6-androstadiene-3β,17β-diol
    • Ma E., and Kim E. Epoxidation and reduction of DHEA, 1,4,6-androstatrien-3-one and 4,6-androstadiene-3β,17β-diol. Molecules 10 (2005) 572-582
    • (2005) Molecules , vol.10 , pp. 572-582
    • Ma, E.1    Kim, E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.