메뉴 건너뛰기




Volumn 63, Issue 9, 1998, Pages 479-483

Novel high-affinity steroidal estrogenic ligands: Synthesis and receptor binding of 11β-vinyl-17α-E/Z-phenylselenovinyl estradiols

Author keywords

Estradiol phenylselenovinyl; Evaluations; Synthesis

Indexed keywords

11BETA VINYL 17ALPHA PHENYLSELENOVINYLESTRADIOL; ESTRADIOL DERIVATIVE; LIGAND; STEROID; UNCLASSIFIED DRUG;

EID: 0031850313     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(98)00052-X     Document Type: Article
Times cited : (17)

References (25)
  • 1
    • 0023808861 scopus 로고
    • The estrogen receptor binds tightly to its response element as a ligand induced homodimer
    • Kumar V., Chambon P. The estrogen receptor binds tightly to its response element as a ligand induced homodimer. Cell. 55:1988;145-156.
    • (1988) Cell , vol.55 , pp. 145-156
    • Kumar, V.1    Chambon, P.2
  • 2
    • 0001431216 scopus 로고
    • Steroid hormone receptors
    • In: Hansch C, Sammes PG, Taylor JB (eds), Pergamon Press, New York
    • Ojasoo T, Raynaud JP, Mornon J-P (1090). Steroid hormone receptors. In: Hansch C, Sammes PG, Taylor JB (eds), Comprehensive Medicinal Chemistry, Vol. 3. Pergamon Press, New York, pp. 1175-1226.
    • (1090) Comprehensive Medicinal Chemistry , vol.3 , pp. 1175-1226
    • Ojasoo, T.1    Raynaud, J.P.2    Mornon J-P3
  • 3
    • 0028283503 scopus 로고
    • Molecular mechanisms of action of steroid/thyroid receptor superfamily members
    • Tsai M.-J., O'Malley B.W. Molecular mechanisms of action of steroid/thyroid receptor superfamily members. Annu Rev Biochem. 63:1994;451-486.
    • (1994) Annu Rev Biochem , vol.63 , pp. 451-486
    • Tsai, M.-J.1    O'Malley, B.W.2
  • 4
    • 0028919090 scopus 로고
    • Estrogen-receptors in human nontarget tissues: Biological and clinical implications
    • Ciocca D.R., Rong L.M.V. Estrogen-receptors in human nontarget tissues Biological and clinical implications . Endocr Rev. 16:1995;35-62.
    • (1995) Endocr Rev , vol.16 , pp. 35-62
    • Ciocca, D.R.1    Rong, L.M.V.2
  • 6
    • 0022473069 scopus 로고
    • Sequence and expression of human estrogen receptor complementary DNA
    • Green G.L., Gilna P., Waterfield M., Baker A., Hort Y., Shine J. Sequence and expression of human estrogen receptor complementary DNA. Science. 231:1986;1150-1154.
    • (1986) Science , vol.231 , pp. 1150-1154
    • Green, G.L.1    Gilna, P.2    Waterfield, M.3    Baker, A.4    Hort, Y.5    Shine, J.6
  • 7
    • 0027141842 scopus 로고
    • DNA recognition by the estrogen receptor: From solution to the crystal
    • Schwabe J.W.R., Chapman L., Finch J.T., Rhodes D., Neuhaus D. DNA recognition by the estrogen receptor From solution to the crystal . Structure. 1:1993;187-204.
    • (1993) Structure , vol.1 , pp. 187-204
    • Schwabe, J.W.R.1    Chapman, L.2    Finch, J.T.3    Rhodes, D.4    Neuhaus, D.5
  • 9
    • 0029643780 scopus 로고
    • Crystal structure of RAR-γ ligand-binding domain bound to all-trans retinoic acid
    • Renaud J.-P., Rochel N., Ruff M., Vivat V., Chambon P., Gronemeyer H., Moras D. Crystal structure of RAR-γ ligand-binding domain bound to all-trans retinoic acid. Nature. 378:1995;681-689.
    • (1995) Nature , vol.378 , pp. 681-689
    • Renaud, J.-P.1    Rochel, N.2    Ruff, M.3    Vivat, V.4    Chambon, P.5    Gronemeyer, H.6    Moras, D.7
  • 11
    • 0031040614 scopus 로고    scopus 로고
    • Different residues of the human estrogen receptor are involved in the recognition of structurally diverse estrogens and antiestrogens
    • Ekena K., Weis K.E., Katzenellenbogen J.A., Katzenellenbogen B.S. Different residues of the human estrogen receptor are involved in the recognition of structurally diverse estrogens and antiestrogens. J Biol Chem. 272:1997;5069-5075.
    • (1997) J Biol Chem , vol.272 , pp. 5069-5075
    • Ekena, K.1    Weis, K.E.2    Katzenellenbogen, J.A.3    Katzenellenbogen, B.S.4
  • 12
    • 0030734795 scopus 로고    scopus 로고
    • Altered ligand binding properties and enhanced stability of a constitutionally active estrogen receptor: Evidence that an open pocket conformation is required for ligand interaction
    • Carlson K.E., Choi I., Gee A., Katzenellenbogen B.S., Katzenellenbogen J.A. Altered ligand binding properties and enhanced stability of a constitutionally active estrogen receptor Evidence that an open pocket conformation is required for ligand interaction . Biochemistry. 36:1997;14897-14905.
    • (1997) Biochemistry , vol.36 , pp. 14897-14905
    • Carlson, K.E.1    Choi, I.2    Gee, A.3    Katzenellenbogen, B.S.4    Katzenellenbogen, J.A.5
  • 13
    • 0023185831 scopus 로고
    • Electrophilic destannylation: Stereospecific introduction of electrophiles at the 21-position of (17α, 20E)-19-norpregna-1,3,5(10), 20-tetraene-3,17β-diols
    • Hanson R.N., El-Wakil H. Electrophilic destannylation Stereospecific introduction of electrophiles at the 21-position of (17α, 20E)-19-norpregna-1,3,5(10), 20-tetraene-3,17β-diols . J Org Chem. 52:1987;3687-3688.
    • (1987) J Org Chem , vol.52 , pp. 3687-3688
    • Hanson, R.N.1    El-Wakil, H.2
  • 14
    • 0001152910 scopus 로고
    • Epoxidation of estra-5(10), 9(11)-diene derivatives: A convenient synthesis of 11β-vinylestrone acetate
    • Napolitano E., Fiaschi R., Hanson R.N. Epoxidation of estra-5(10), 9(11)-diene derivatives A convenient synthesis of 11β-vinylestrone acetate . Gazz Chem Ital. 170:1990;323-326.
    • (1990) Gazz Chem Ital , vol.170 , pp. 323-326
    • Napolitano, E.1    Fiaschi, R.2    Hanson, R.N.3
  • 15
    • 0025945627 scopus 로고
    • Structure-activity relationships of estrogenic ligands: Synthesis and evaluation of (17α, 20E)- And (17α, 20Z)-21-halo-19-norpregna-1,3,5(10),20-tetraene-3,17β-diols
    • Napolitano E., Fiaschi R., Hanson R.N. Structure-activity relationships of estrogenic ligands Synthesis and evaluation of (17α, 20E)- and (17α, 20Z)-21-halo-19-norpregna-1,3,5(10),20-tetraene-3,17β-diols . J Med Chem. 34:1991;2754-2759.
    • (1991) J Med Chem , vol.34 , pp. 2754-2759
    • Napolitano, E.1    Fiaschi, R.2    Hanson, R.N.3
  • 16
    • 0025223142 scopus 로고
    • Synthesis and estrogen receptor binding of novel 11β-substituted estra-1,3,5(10)-triene-3,17β-diols
    • Hanson R.N., Napolitano E., Fiaschi R. Synthesis and estrogen receptor binding of novel 11β-substituted estra-1,3,5(10)-triene-3,17β-diols. J Med Chem. 33:1990;3153-3160.
    • (1990) J Med Chem , vol.33 , pp. 3153-3160
    • Hanson, R.N.1    Napolitano, E.2    Fiaschi, R.3
  • 17
    • 0029891668 scopus 로고    scopus 로고
    • Synthesis and estrogen receptor binding of (17α, 20E)-and (17α, 20Z)-21-phenylthio- And 21-phenylseleno-19-norpregna-1,3,5(10), 20-tetraene-3, 17β-diols
    • Napolitano E., Fiaschi R., Herman L.W., Hanson R.N. Synthesis and estrogen receptor binding of (17α, 20E)-and (17α, 20Z)-21-phenylthio- and 21-phenylseleno-19-norpregna-1,3,5(10), 20-tetraene-3, 17β-diols. Steroids. 61:1996;384-389.
    • (1996) Steroids , vol.61 , pp. 384-389
    • Napolitano, E.1    Fiaschi, R.2    Herman, L.W.3    Hanson, R.N.4
  • 18
    • 0030474378 scopus 로고    scopus 로고
    • Stereochemical probes for the estrogen receptor: Synthesis and receptor binding of (17α, 20E/Z)-21-phenyl-19-norpregna-1,3,5(10), 20-tetraene-3,17β-diols
    • Hanson R.N., Herman L.W., Fiaschi R., Napolitano E. Stereochemical probes for the estrogen receptor Synthesis and receptor binding of (17α, 20E/Z)-21-phenyl-19-norpregna-1,3,5(10), 20-tetraene-3,17β-diols . Steroids. 31:1996;718-722.
    • (1996) Steroids , vol.31 , pp. 718-722
    • Hanson, R.N.1    Herman, L.W.2    Fiaschi, R.3    Napolitano, E.4
  • 19
    • 0032547897 scopus 로고    scopus 로고
    • Synthesis and evaluation of 11β-substituted-21-chloro iodo-(17α, 20E/Z)-19-norpregna-1,3,5(10),20-tetraene-3,17βdiols: High affinity ligands for the estrogen receptor
    • (In press)
    • Hanson RN, Napolitano E, Fiaschi R. Synthesis and evaluation of 11β-substituted-21-chloro iodo-(17α, 20E/Z)-19-norpregna-1,3,5(10),20-tetraene-3,17βdiols: High affinity ligands for the estrogen receptor. J Med Chem (In press).
    • J Med Chem
    • Hanson, R.N.1    Napolitano, E.2    Fiaschi, R.3
  • 20
    • 0002714675 scopus 로고
    • Rapid chromatographic technique for preparative separations with moderate resolution
    • Still W.C., Kahn M., Mitra A. Rapid chromatographic technique for preparative separations with moderate resolution. J Org Chem. 43:1978;2923-2925.
    • (1978) J Org Chem , vol.43 , pp. 2923-2925
    • Still, W.C.1    Kahn, M.2    Mitra, A.3
  • 21
    • 0015902629 scopus 로고
    • Reagents for photoaffinity labeling of estrogen binding protein. The binding affinity of some azido and diazo derivatives of estradiol, estrone and hexestrol for the estrogen binding protein of rat uterus
    • Katzenellenbogen J.A., Johnson J.H. Jr, Myers H.M. Reagents for photoaffinity labeling of estrogen binding protein. The binding affinity of some azido and diazo derivatives of estradiol, estrone and hexestrol for the estrogen binding protein of rat uterus. Biochemistry. 12:1973;4085-4092.
    • (1973) Biochemistry , vol.12 , pp. 4085-4092
    • Katzenellenbogen, J.A.1    Johnson J.H., Jr.2    Myers, H.M.3
  • 22
    • 0017598113 scopus 로고
    • Estrogen photoaffinity labels. II. Reversible binding and covalent attachment of photosensitive hexestrol derivatives to the uterus estrogen receptor
    • Katzenellenbogen J.R., Carlson K.E., Johnson J.H. Jr, Meyers H.M. Estrogen photoaffinity labels. II. Reversible binding and covalent attachment of photosensitive hexestrol derivatives to the uterus estrogen receptor. Biochemistry. 16:1977;1970-1976.
    • (1977) Biochemistry , vol.16 , pp. 1970-1976
    • Katzenellenbogen, J.R.1    Carlson, K.E.2    Johnson J.H., Jr.3    Meyers, H.M.4
  • 23
    • 0031059270 scopus 로고    scopus 로고
    • The estradiol pharmacophore: Ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site
    • Anstead G.M., Carlson K.E., Katzenellenbogen J.A. The estradiol pharmacophore Ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site . Steroids. 62:1997;268-303.
    • (1997) Steroids , vol.62 , pp. 268-303
    • Anstead, G.M.1    Carlson, K.E.2    Katzenellenbogen, J.A.3
  • 25
    • 0028063420 scopus 로고
    • Quantitative structure-activity relationships/comparative molecular field analysis (QSAR/CoMFA) for receptor-binding properties of halogenated estradiol derivatives
    • Gantchev T.G., Ali H., van Lier J.E. Quantitative structure-activity relationships/comparative molecular field analysis (QSAR/CoMFA) for receptor-binding properties of halogenated estradiol derivatives. J Med Chem. 37:1994;4164-4176.
    • (1994) J Med Chem , vol.37 , pp. 4164-4176
    • Gantchev, T.G.1    Ali, H.2    Van Lier, J.E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.