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Volumn 71, Issue 8, 2006, Pages 706-711

Facile ring opening of 2,3-epoxy-steroids with aromatic amines in ionic liquids

Author keywords

2,3 Epoxy derivatives; Aminoalcohols; Ionic liquids; Steroids

Indexed keywords

2ALPHA,3ALPHA EPOXY 5ALPHA ANDROSTAN 17 ONE; 2BETA HYDROXY 3ALPHA [(4' METHYLPHENYL)AMINO] 5ALPHA ANDROST 17 ONE; 2BETA,3ALPHA DIHYDROXY 5ALPHA ANDROST 17 ONE; 2BETA,3ALPHA EPOXY 17 [(4'METHYLPHENYL)AMINO] 5ALPHA ANDROSTANE; 3ALPHA HYDROXY 2BETA (4 MORPHOLINYL) 5ALPHA ANDROST 17 ONE; 3ALPHA HYDROXY 2BETA (PHENYLAMINO) 5ALPHA ANDROST 17 ONE; 3ALPHA HYDROXY 2BETA [(4' ACETYLYPHENYL)AMINO] 5ALPHA ANDROST 17 ONE; 3ALPHA HYDROXY 2BETA [(4' HYDROXYPHENYL)AMINO] 5ALPHA ANDROST 17 ONE; 3ALPHA HYDROXY 2BETA [(4' METHYLPHENYL)AMINO] 5ALPHA ANDROST 17 ONE; 3ALPHA HYDROXY 2BETA [(4' NITROPHENYL)AMINO] 5ALPHA ANDROST 17 ONE; 4 METHYL ANILINE; AMINOALCOHOL; AROMATIC AMINE; DIOXANE; EPOXIDE; IONIC LIQUID; MORPHOLINE; PRASTERONE; SOLVENT; STEROID; UNCLASSIFIED DRUG;

EID: 33745603175     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2006.04.006     Document Type: Article
Times cited : (17)

References (29)
  • 1
    • 0034697199 scopus 로고    scopus 로고
    • The synthesis of vicinal amino alcohols
    • Bergmeier S.C. The synthesis of vicinal amino alcohols. Tetrahedron 56 (2000) 2561-2576
    • (2000) Tetrahedron , vol.56 , pp. 2561-2576
    • Bergmeier, S.C.1
  • 2
    • 0035991756 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of neuromuscular blocking agents
    • Tuba Z., Mahó S., and Vizi E.S. Synthesis and structure-activity relationships of neuromuscular blocking agents. Curr Med Chem 9 (2002) 1241-1253
    • (2002) Curr Med Chem , vol.9 , pp. 1241-1253
    • Tuba, Z.1    Mahó, S.2    Vizi, E.S.3
  • 3
    • 0032894778 scopus 로고    scopus 로고
    • A novel aminosteroid is active for proliferation inhibition and differentiation induction of human acute myeloid leukemia HL-60 cells
    • He Q., and Jiang D.Z. A novel aminosteroid is active for proliferation inhibition and differentiation induction of human acute myeloid leukemia HL-60 cells. Leuk Res 23 (1999) 369-372
    • (1999) Leuk Res , vol.23 , pp. 369-372
    • He, Q.1    Jiang, D.Z.2
  • 4
    • 0035042498 scopus 로고    scopus 로고
    • The effects and mechanisms of a novel 2-aminosteroid on murine WEHI-3B leukemia cells in vitro and in vivo
    • He Q., and Na X. The effects and mechanisms of a novel 2-aminosteroid on murine WEHI-3B leukemia cells in vitro and in vivo. Leuk Res 25 (2001) 455-461
    • (2001) Leuk Res , vol.25 , pp. 455-461
    • He, Q.1    Na, X.2
  • 5
    • 33745629998 scopus 로고    scopus 로고
    • Hewett CL, Savage DS, inventors; Organon Laboratories Ltd., United Kingdom, assignee. Improvements in or relating to new 2β,16β-diamino-androstanes. GB Patent 1,138,605 (January 1, 1969).
  • 6
    • 33745586940 scopus 로고    scopus 로고
    • Savage DS, Sleigh T, Taylor R, inventors; Akzo NV, The Netherlands, assignee. Novel 2β,16β-diamino-androstanes. Eur Patent 0,288,102 (October 26, 1988).
  • 7
    • 33745606075 scopus 로고    scopus 로고
    • Sleigh T, Savage DS, Clark JK, inventors; Akzo NV, The Netherlands, assignee. Novel 16-homo-piperidino-androstane derivatives and processes for their preparation. Eur Patent 0,330,253 (30 August 1989).
  • 8
    • 33745627964 scopus 로고    scopus 로고
    • Campbell AC, inventor; Akzo Nobel NV, The Netherlands, assignee. Substituted 2β-morfolino-androstane derivatives. Eur Patent 0,656,365 (7 January 1995).
  • 9
    • 37049126877 scopus 로고
    • Amino-steroids. Part III. 2- and 3-Amino-5α-androstanes
    • Hewett C.L., and Savage D.S. Amino-steroids. Part III. 2- and 3-Amino-5α-androstanes. J Chem Soc (C) (1968) 1134-1140
    • (1968) J Chem Soc (C) , pp. 1134-1140
    • Hewett, C.L.1    Savage, D.S.2
  • 10
    • 0016671060 scopus 로고
    • Darstellung von 10β-heterosubstituierten Steroiden
    • Ponsold K., Schade W., and Wunderwald M. Darstellung von 10β-heterosubstituierten Steroiden. J Prakt Chem 317 (1975) 307-318
    • (1975) J Prakt Chem , vol.317 , pp. 307-318
    • Ponsold, K.1    Schade, W.2    Wunderwald, M.3
  • 11
    • 33745591819 scopus 로고
    • Reaction of aniline with steroidal α-epoxides
    • Agarwal V., Husain S., and Gupta K.C. Reaction of aniline with steroidal α-epoxides. J Indian Chem Soc 72 (1995) 639-640
    • (1995) J Indian Chem Soc , vol.72 , pp. 639-640
    • Agarwal, V.1    Husain, S.2    Gupta, K.C.3
  • 12
    • 0033534609 scopus 로고    scopus 로고
    • An efficient method for cleavage of epoxides with aromatic amines
    • Sekar G., and Singh V.K. An efficient method for cleavage of epoxides with aromatic amines. J Org Chem 64 (1999) 287-289
    • (1999) J Org Chem , vol.64 , pp. 287-289
    • Sekar, G.1    Singh, V.K.2
  • 13
    • 0742287246 scopus 로고    scopus 로고
    • Bismuth triflate-catalyzed mild and efficient epoxide opening by aromatic amines under aqueous conditions
    • Ollevier T., and Lavie-Compin G. Bismuth triflate-catalyzed mild and efficient epoxide opening by aromatic amines under aqueous conditions. Tetrahedron Lett 45 (2004) 49-52
    • (2004) Tetrahedron Lett , vol.45 , pp. 49-52
    • Ollevier, T.1    Lavie-Compin, G.2
  • 14
    • 0037190851 scopus 로고    scopus 로고
    • An efficient method for the ring opening of epoxides with aromatic amines catalyzed by bismuth trichloride
    • Ollevier T., and Lavie-Compin G. An efficient method for the ring opening of epoxides with aromatic amines catalyzed by bismuth trichloride. Tetrahedron Lett 43 (2002) 7891-7893
    • (2002) Tetrahedron Lett , vol.43 , pp. 7891-7893
    • Ollevier, T.1    Lavie-Compin, G.2
  • 15
    • 0034755750 scopus 로고    scopus 로고
    • Zirconium sulfophenyl phosphonate as a heterogeneous catalyst in the preparation of β-amino alcohols from epoxides
    • Curini M., Epifano F., Marcotullio M.C., and Rosati O. Zirconium sulfophenyl phosphonate as a heterogeneous catalyst in the preparation of β-amino alcohols from epoxides. Eur J Org Chem (2001) 4149-4152
    • (2001) Eur J Org Chem , pp. 4149-4152
    • Curini, M.1    Epifano, F.2    Marcotullio, M.C.3    Rosati, O.4
  • 16
    • 1942456881 scopus 로고    scopus 로고
    • Transition metal-based Lewis acid catalyzed ring opening of epoxides using amines under solvent-free conditions
    • Zhao P.Q., Xu L.W., and Xia C.G. Transition metal-based Lewis acid catalyzed ring opening of epoxides using amines under solvent-free conditions. Synlett (2004) 846-850
    • (2004) Synlett , pp. 846-850
    • Zhao, P.Q.1    Xu, L.W.2    Xia, C.G.3
  • 17
    • 0034613328 scopus 로고    scopus 로고
    • Facile ring opening of oxiranes with aromatic amines in fluoro alcohols
    • Das U., Crousse B., Kesavan V., Bonnet-Delpon D., and Bégué J.P. Facile ring opening of oxiranes with aromatic amines in fluoro alcohols. J Org Chem 65 (2000) 6749-6751
    • (2000) J Org Chem , vol.65 , pp. 6749-6751
    • Das, U.1    Crousse, B.2    Kesavan, V.3    Bonnet-Delpon, D.4    Bégué, J.P.5
  • 18
    • 2542462020 scopus 로고    scopus 로고
    • An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines
    • Chakraborti A.K., Rudrawar S., and Kondaskar A. An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines. Org Biomol Chem 2 (2004) 1277-1280
    • (2004) Org Biomol Chem , vol.2 , pp. 1277-1280
    • Chakraborti, A.K.1    Rudrawar, S.2    Kondaskar, A.3
  • 19
    • 9644264300 scopus 로고    scopus 로고
    • Ionic liquids in catalysis
    • Welton T. Ionic liquids in catalysis. Coord Chem Rev 248 (2004) 2459-2477
    • (2004) Coord Chem Rev , vol.248 , pp. 2459-2477
    • Welton, T.1
  • 20
    • 0035923960 scopus 로고    scopus 로고
    • New developments in catalysis using ionic liquids
    • Gordon C.M. New developments in catalysis using ionic liquids. Appl Catal A 222 (2001) 101-117
    • (2001) Appl Catal A , vol.222 , pp. 101-117
    • Gordon, C.M.1
  • 22
    • 14644432451 scopus 로고    scopus 로고
    • Regioselective enzymatic acylation of vicinal diols of steroids
    • Cruz Silva M.M., Riva S., and Sá e Melo M.L. Regioselective enzymatic acylation of vicinal diols of steroids. Tetrahedron 65 (2005) 3065-3073
    • (2005) Tetrahedron , vol.65 , pp. 3065-3073
    • Cruz Silva, M.M.1    Riva, S.2    Sá e Melo, M.L.3
  • 24
    • 33745619140 scopus 로고    scopus 로고
    • Klimstra PD, Counsell RE, inventors; Searle & Co., Chicago, USA, assignee. Optionally N-substituted 17-oxygenated-2-amino-5α-androstan-3-ols. US Patent 3,238,194 (December 12 1962).
  • 25
    • 0000269981 scopus 로고
    • Über Steroide und Sexualhormone. 2α,3α- und 2β,3β-Oxido-cholestane; Konfiguration der 2-oxy-cholestane
    • Fürst A., and Plattner P.A. Über Steroide und Sexualhormone. 2α,3α- und 2β,3β-Oxido-cholestane; Konfiguration der 2-oxy-cholestane. Helv Chim Acta 32 (1949) 275-283
    • (1949) Helv Chim Acta , vol.32 , pp. 275-283
    • Fürst, A.1    Plattner, P.A.2
  • 26
    • 37049152584 scopus 로고
    • The stereochemistry of cyclohexane derivatives
    • Barton D.H.R. The stereochemistry of cyclohexane derivatives. J Chem Soc (1953) 1027-1040
    • (1953) J Chem Soc , pp. 1027-1040
    • Barton, D.H.R.1
  • 28
    • 0026317375 scopus 로고
    • 13C NMR spectroscopy and molecular mechanics study of 3α-hydroxy-2β-(4-morpholinyl)-5αH-androst-17-one
    • 13C NMR spectroscopy and molecular mechanics study of 3α-hydroxy-2β-(4-morpholinyl)-5αH-androst-17-one. J Am Chem Soc 113 (1991) 9785-9790
    • (1991) J Am Chem Soc , vol.113 , pp. 9785-9790
    • Fielding, L.1    Grant, G.H.2
  • 29
    • 0036329105 scopus 로고    scopus 로고
    • 3+ catalyzed regioselective ring opening of epoxides with aromatic amines
    • 3+ catalyzed regioselective ring opening of epoxides with aromatic amines. Synth Commun 32 (2002) 2307-2312
    • (2002) Synth Commun , vol.32 , pp. 2307-2312
    • Swamy, N.R.1    Kondaji, G.2    Nagaiah, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.