메뉴 건너뛰기




Volumn 71, Issue 5, 2006, Pages 334-342

Synthesis of 7α-substituted derivatives of 17β-estradiol

Author keywords

Chemical synthesis; Estrogen receptor; Pure antagonist

Indexed keywords

1 IODO 6 BENZYLOXYHEXANE; 3 HYDROXY 17BETA METHOXYMETHOXY 7ALPHA (6 HYDROXYHEXANYL)ESTRA 1,3,5(10) TRIENE; 3 METHOXY 7ALPHA (6 BENZYLOXYHEXANYL)ESTRA 1,3,5(10) TRIEN 17BETA OL; 3,17BETA BIS(ACETOXY) 7ALPHA (6 ACETOXYHEXANYL)ESTRA 1,3,5(10) TRIENE; 3,17BETA BIS(ACETOXY) 7ALPHA (6 BENZYLOXYHEXANYL)ESTRA 1,3,5(10) TRIEN 6 ONE; 3,17BETA BIS(ACETOXY) 7ALPHA (6 HEXANYLALDEHYDE)ESTRA 1,3,5(10) TRIENE; 3,17BETA BIS(ACETOXY) 7ALPHA (6 HYDROXYHEXANYL)ESTRA 1,3,5(10) TRIENE; 3,17BETA BIS(HYDROXY) 7ALPHA (6 BENZYLOXYHEXANYL)ESTRA 1,3,5(10) TRIEN 6 ONE; 3,17BETA BIS(HYDROXY) 7ALPHA (6 BENZYLOXYHEXANYL)ESTRA 1,3,5(10) TRIENE; 3,17BETA BIS(METHOXYMETHOXY) 7ALPHA (6 BENZYLOXYHEXANYL)ESTRA 1,3,5(10) TRIEN 6 OL; 3,17BETA BIS(METHOXYMETHOXY) 7ALPHA (6 BENZYLOXYHEXANYL)ESTRA 1,3,5(10) TRIEN 6 ONE; 3,17BETA BIS(METHOXYMETHOXY) 7ALPHA (6 BENZYLOXYHEXANYL)ESTRA 1,3,5(10) TRIENE; 3,17BETA BIS(METHOXYMETHOXY) 7ALPHA (6 HYDROXYHEXANYL)ESTRA 1,3,5(10) TRIEN 6 OL; 3,17BETA BIS(METHOXYMETHOXY) 7ALPHA (6 HYDROXYHEXANYL)ESTRA 1,3,5(10) TRIENE; 3,17BETA BIS(METHOXYMETHOXY)ESTRA 1,3,5(10) TRIEN 6 OL; 3,17BETA BIS(METHOXYMETHOXY)ESTRA 1,3,5(10) TRIEN 6 ONE; 7ALPHA (6 HYDROXYHEXANYL) 17BETA ESTRADIOL; ACETIC ACID; ANTIESTROGEN; BENZYL DERIVATIVE; ESTRADIOL DERIVATIVE; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FULVESTRANT; HYDROXYL GROUP; UNCLASSIFIED DRUG; 1-IODO-6-BENZYLOXYHEXANE; BOVINE SERUM ALBUMIN; DRUG DERIVATIVE; ESTRADIOL; ETHER DERIVATIVE; HEXANE; RECOMBINANT PROTEIN;

EID: 33646048615     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2005.11.008     Document Type: Article
Times cited : (21)

References (31)
  • 1
    • 0035888074 scopus 로고    scopus 로고
    • Estimating the world cancer burden: Globocan
    • Parkin D.M., Bray F., and Ferlay J. Estimating the world cancer burden: Globocan. Int J Cancer 94 (2001) 153-156
    • (2001) Int J Cancer , vol.94 , pp. 153-156
    • Parkin, D.M.1    Bray, F.2    Ferlay, J.3
  • 2
    • 0029436096 scopus 로고
    • Third annual William L. McGuire Memorial Lecture. Studies on the estrogen receptor in breast cancer-20 years as a target for the treatment and prevention of cancer
    • Jordan V.C. Third annual William L. McGuire Memorial Lecture. Studies on the estrogen receptor in breast cancer-20 years as a target for the treatment and prevention of cancer. Breast Cancer Res Treat 36 (1995) 267-285
    • (1995) Breast Cancer Res Treat , vol.36 , pp. 267-285
    • Jordan, V.C.1
  • 3
    • 0031778177 scopus 로고    scopus 로고
    • Basic guide to the mechanisms of antiestrogen action
    • MacGregor J.I., and Jordan V.C. Basic guide to the mechanisms of antiestrogen action. Pharmacol Rev 50 (1998) 151-196
    • (1998) Pharmacol Rev , vol.50 , pp. 151-196
    • MacGregor, J.I.1    Jordan, V.C.2
  • 4
    • 1842684035 scopus 로고    scopus 로고
    • Fulvestrant: an estrogen receptor antagonist with a novel mechanism of action
    • Osborne C.K., Wakeling A., and Nicholson R.I. Fulvestrant: an estrogen receptor antagonist with a novel mechanism of action. Br J Cancer 90 Suppl. 1 (2004) S2-S6
    • (2004) Br J Cancer , vol.90 , Issue.SUPPL. 1
    • Osborne, C.K.1    Wakeling, A.2    Nicholson, R.I.3
  • 6
    • 0242721582 scopus 로고    scopus 로고
    • Fulvestrant: an estrogen receptor antagonist that downregulates the estrogen receptor
    • Jones S.E. Fulvestrant: an estrogen receptor antagonist that downregulates the estrogen receptor. Semin Oncol 30 5 Suppl. 16 (2003) 14-20
    • (2003) Semin Oncol , vol.30 , Issue.5 SUPPL. 16 , pp. 14-20
    • Jones, S.E.1
  • 7
    • 0031434833 scopus 로고    scopus 로고
    • A stereoselective synthesis of 7α-(3-carboxypropyl) estradiol from a noncontrolled substance
    • Adamczyk M., Johnson D., and Reddy E. A stereoselective synthesis of 7α-(3-carboxypropyl) estradiol from a noncontrolled substance. Steroids 62 (1997) 771-775
    • (1997) Steroids , vol.62 , pp. 771-775
    • Adamczyk, M.1    Johnson, D.2    Reddy, E.3
  • 8
    • 0037034312 scopus 로고    scopus 로고
    • Synthesis of chimeric 7α-substituted estradiol derivatives linked to cholesterol and cholesterylamine
    • Hussey S.L., He E., and Peterson B.R. Synthesis of chimeric 7α-substituted estradiol derivatives linked to cholesterol and cholesterylamine. Org Lett 4 (2002) 415-418
    • (2002) Org Lett , vol.4 , pp. 415-418
    • Hussey, S.L.1    He, E.2    Peterson, B.R.3
  • 9
    • 0345440144 scopus 로고    scopus 로고
    • Synthesis and binding affinities of novel re-containing 7α-substituted estradiol complexes: models for breast cancer imaging agents
    • Skaddan M.B., Wust F.R., and Katzenellenbogen J.A. Synthesis and binding affinities of novel re-containing 7α-substituted estradiol complexes: models for breast cancer imaging agents. J Org Chem 64 (1999) 8108-8121
    • (1999) J Org Chem , vol.64 , pp. 8108-8121
    • Skaddan, M.B.1    Wust, F.R.2    Katzenellenbogen, J.A.3
  • 10
    • 0036026463 scopus 로고    scopus 로고
    • Synthesis of 16α-fluoro ICI, 182,780 derivatives: powerful antiestrogens to image estrogen receptor densities in breast cancer by positron emission tomography
    • Seimbille Y., Benard F., and van Lier J.E. Synthesis of 16α-fluoro ICI, 182,780 derivatives: powerful antiestrogens to image estrogen receptor densities in breast cancer by positron emission tomography. J Chem Soc, Perkin Trans 1 (2002) 2275-2281
    • (2002) J Chem Soc, Perkin Trans , vol.1 , pp. 2275-2281
    • Seimbille, Y.1    Benard, F.2    van Lier, J.E.3
  • 11
    • 0037028969 scopus 로고    scopus 로고
    • A rationally designed genotoxin that selectively destroys estrogen receptor-positive breast cancer cells
    • Mitra K., Marquis J.C., Hillier S.M., Rye P.T., Zayas B., Lee A.S., et al. A rationally designed genotoxin that selectively destroys estrogen receptor-positive breast cancer cells. J Am Chem Soc 124 (2002) 1862-1863
    • (2002) J Am Chem Soc , vol.124 , pp. 1862-1863
    • Mitra, K.1    Marquis, J.C.2    Hillier, S.M.3    Rye, P.T.4    Zayas, B.5    Lee, A.S.6
  • 12
    • 0037414262 scopus 로고    scopus 로고
    • Synthesis of a β-estradiol-biotin chimera that potently heterodimerizes estrogen receptor and strepavidin proteins in a yeast three-hybrid system
    • Hussey S.L., Muddana S.S., and Peterson B.R. Synthesis of a β-estradiol-biotin chimera that potently heterodimerizes estrogen receptor and strepavidin proteins in a yeast three-hybrid system. J Am Chem Soc 125 (2003) 3692-3693
    • (2003) J Am Chem Soc , vol.125 , pp. 3692-3693
    • Hussey, S.L.1    Muddana, S.S.2    Peterson, B.R.3
  • 13
    • 0034911153 scopus 로고    scopus 로고
    • Characterization of the NADPH-dependent metabolism of 17β-estradiol to multiple metabolites by human liver microsomes and selectively expressed human cytochrome P450 3A4 and 3A5
    • Lee A.J., Kosh J.W., Conney A.H., and Zhu B.T. Characterization of the NADPH-dependent metabolism of 17β-estradiol to multiple metabolites by human liver microsomes and selectively expressed human cytochrome P450 3A4 and 3A5. J Pharmacol Exp Ther 298 (2001) 420-432
    • (2001) J Pharmacol Exp Ther , vol.298 , pp. 420-432
    • Lee, A.J.1    Kosh, J.W.2    Conney, A.H.3    Zhu, B.T.4
  • 15
    • 2142761525 scopus 로고    scopus 로고
    • Concentration-dependent mitogenic and antiproliferative actions of 2-methoxyestradiol in estrogen receptor-positive human breast cancer cells
    • Liu Z.J., and Zhu B.T. Concentration-dependent mitogenic and antiproliferative actions of 2-methoxyestradiol in estrogen receptor-positive human breast cancer cells. J Steroid Biochem Mol Biol 88 (2004) 265-275
    • (2004) J Steroid Biochem Mol Biol , vol.88 , pp. 265-275
    • Liu, Z.J.1    Zhu, B.T.2
  • 16
    • 0001474301 scopus 로고
    • Benzylic oxidation using tert-butyl hydroperoxide in the presence of chromium hexacarbonyl
    • Pearson J.A., and Han G.R. Benzylic oxidation using tert-butyl hydroperoxide in the presence of chromium hexacarbonyl. J Org Chem 50 (1985) 2791
    • (1985) J Org Chem , vol.50 , pp. 2791
    • Pearson, J.A.1    Han, G.R.2
  • 17
    • 84950024939 scopus 로고
    • A convenient method of benzylic oxidation with pyridinium chlorochromate
    • Rather R., Saxena N., and Chandrasekaran S. A convenient method of benzylic oxidation with pyridinium chlorochromate. Synth Commun 16 (1986) 1493
    • (1986) Synth Commun , vol.16 , pp. 1493
    • Rather, R.1    Saxena, N.2    Chandrasekaran, S.3
  • 18
    • 84918616617 scopus 로고
    • Fluorine- and trifluoromethyl-substituted toluenes: site selective metalation of aromatic or benzylic positions
    • Takagishi S., and Schlosser M. Fluorine- and trifluoromethyl-substituted toluenes: site selective metalation of aromatic or benzylic positions. Synlett (1991) 119-121
    • (1991) Synlett , pp. 119-121
    • Takagishi, S.1    Schlosser, M.2
  • 19
    • 0029611196 scopus 로고
    • 6-Oxoestradiols from estradiols: exploiting site selective metalation of aralkyl systems with superbases
    • Tedesco R., Fiaschi R., and Napolitano E. 6-Oxoestradiols from estradiols: exploiting site selective metalation of aralkyl systems with superbases. Synthesis (1995) 1493-1495
    • (1995) Synthesis , pp. 1493-1495
    • Tedesco, R.1    Fiaschi, R.2    Napolitano, E.3
  • 20
    • 84954645633 scopus 로고
    • Improved preparation of 3β,17β-diacetoxyoestra-1,3,5(10)-trien-6-one
    • Akanni A.O., and Marples B.A. Improved preparation of 3β,17β-diacetoxyoestra-1,3,5(10)-trien-6-one. Synth Commun 14 (1984) 713-715
    • (1984) Synth Commun , vol.14 , pp. 713-715
    • Akanni, A.O.1    Marples, B.A.2
  • 21
    • 0026326830 scopus 로고
    • Synthesis and mechanism of hydrolysis of estrogen 6-sulfates: model compounds for demonstrating the carcinogenesis of estrogen
    • Takagi H., Komatsu K., and Yoshizawa I. Synthesis and mechanism of hydrolysis of estrogen 6-sulfates: model compounds for demonstrating the carcinogenesis of estrogen. Steroids 56 (1991) 173-179
    • (1991) Steroids , vol.56 , pp. 173-179
    • Takagi, H.1    Komatsu, K.2    Yoshizawa, I.3
  • 22
    • 0012302982 scopus 로고
    • Pyridinium chlorochromate-mediated allylic and benzylic oxidation
    • Parish E.J., Chitrakorn S., and Wei T.Y. Pyridinium chlorochromate-mediated allylic and benzylic oxidation. Synth Commun 16 (1986) 1371-1375
    • (1986) Synth Commun , vol.16 , pp. 1371-1375
    • Parish, E.J.1    Chitrakorn, S.2    Wei, T.Y.3
  • 23
    • 12644312578 scopus 로고
    • Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chloride
    • Mancuso A.J., Huang S.L., and Swern D. Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chloride. J Org Chem 43 (1978) 2480-2482
    • (1978) J Org Chem , vol.43 , pp. 2480-2482
    • Mancuso, A.J.1    Huang, S.L.2    Swern, D.3
  • 25
    • 0002857320 scopus 로고    scopus 로고
    • A new highly efficient procedure for the monobenzylation of symmetrical diols
    • Bessodes M., and Boukarim C. A new highly efficient procedure for the monobenzylation of symmetrical diols. Synlett (1996) 1119-1120
    • (1996) Synlett , pp. 1119-1120
    • Bessodes, M.1    Boukarim, C.2
  • 26
    • 0030829697 scopus 로고    scopus 로고
    • An expeditious route to 7α-substituted estradiol derivatives
    • Tedesco R., Katzenellenbogen J.A., and Napolitano E. An expeditious route to 7α-substituted estradiol derivatives. Tetrahedron Lett 38 (1997) 7997-8000
    • (1997) Tetrahedron Lett , vol.38 , pp. 7997-8000
    • Tedesco, R.1    Katzenellenbogen, J.A.2    Napolitano, E.3
  • 27
    • 85022494272 scopus 로고
    • A simple and convenient one-step method for the reductive deoxygenation of aryl ketones to hydrocarbons
    • Srikrishana A., Sattigeri J.A., Viswajanani R., and Yelamaggad C.V. A simple and convenient one-step method for the reductive deoxygenation of aryl ketones to hydrocarbons. Synlett (1995) 93-94
    • (1995) Synlett , pp. 93-94
    • Srikrishana, A.1    Sattigeri, J.A.2    Viswajanani, R.3    Yelamaggad, C.V.4
  • 28
    • 33646019042 scopus 로고
    • Hydrogenolysis of carbonyl derivatives as a route to pure aliphatic-aromatic hydrocarbons
    • Burnham J.W., and Eisenbraun E.J. Hydrogenolysis of carbonyl derivatives as a route to pure aliphatic-aromatic hydrocarbons. J Org Chem 36 (1971) 737-738
    • (1971) J Org Chem , vol.36 , pp. 737-738
    • Burnham, J.W.1    Eisenbraun, E.J.2
  • 30
    • 33646031614 scopus 로고    scopus 로고
    • Huang M. Reducing steroid ketones to their corresponding methylene analogs. US Patent 2,648,686. Merck & Co. Inc.; 11 August 1953.
  • 31
    • 0000495151 scopus 로고
    • Reduction of steroid ketones and other carbonyl compounds by modified Wolff-Kishner method
    • Huang M. Reduction of steroid ketones and other carbonyl compounds by modified Wolff-Kishner method. J Am Chem Soc 71 (1949) 3301-3303
    • (1949) J Am Chem Soc , vol.71 , pp. 3301-3303
    • Huang, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.