메뉴 건너뛰기




Volumn 47, Issue 21, 2004, Pages 5021-5040

Design and synthesis of aryl diphenolic azoles as potent and selective estrogen receptor-β ligands

Author keywords

[No Author keywords available]

Indexed keywords

2 (3 FLUORO 4 HYDROXYPHENYL) 7 VINYL 5 BENZOXAZOLOL; AGENTS INTERACTING WITH TRANSMITTER, HORMONE OR DRUG RECEPTORS; BAZEDOXIFENE; BENZOXAZOLE DERIVATIVE; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ESTROGEN RECEPTOR BETA AGONIST; ETHINYLESTRADIOL; FLUTAMIDE; HLA B27 ANTIGEN; PROPYLPYRAZOLETRIOL; PYRAZOLE DERIVATIVE; PYRROLE DERIVATIVE; TESTOSTERONE PROPIONATE; UNCLASSIFIED DRUG;

EID: 4744376265     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049719y     Document Type: Article
Times cited : (258)

References (49)
  • 5
    • 0028283503 scopus 로고
    • Molecular Mechanisms of Action of Steroid/Thyroid Receptors Superfamily Members
    • Tsai, M. J.; O'Malley, B. W. Molecular Mechanisms of Action of Steroid/Thyroid Receptors Superfamily Members. Annu. Rev. Biochem. 1994, 63, 451-486.
    • (1994) Annu. Rev. Biochem. , vol.63 , pp. 451-486
    • Tsai, M.J.1    O'Malley, B.W.2
  • 6
    • 0022653964 scopus 로고
    • Human oestrogen receptor cDNA: Sequence, expression and homology to v-erb-A
    • Green, S.; Walter, P.; Kumar, V.; Krust, A.; Bornert, J. M.; Argos, P.; Chambon, P. Human oestrogen receptor cDNA: sequence, expression and homology to v-erb-A. Nature 1986, 320, 134-139.
    • (1986) Nature , vol.320 , pp. 134-139
    • Green, S.1    Walter, P.2    Kumar, V.3    Krust, A.4    Bornert, J.M.5    Argos, P.6    Chambon, P.7
  • 14
    • 0036828135 scopus 로고    scopus 로고
    • Characterization of the biological roles of the estrogen receptors, ER alpha and ER beta, in estrogen target tissues in vivo through the use of an alpha-selective ligand
    • Harris, H, A.; Katzenellenbogen, J. A.; Katzenellenbogen, B. S. Characterization of the biological roles of the estrogen receptors, ER alpha and ER beta, in estrogen target tissues in vivo through the use of an alpha-selective ligand. Endocrinology 2002, 143, 4172-4177.
    • (2002) Endocrinology , vol.143 , pp. 4172-4177
    • Harris, H.A.1    Katzenellenbogen, J.A.2    Katzenellenbogen, B.S.3
  • 16
    • 0038003849 scopus 로고    scopus 로고
    • Constrained phytoestrogens and analogues as ERβ sélective ligands
    • (b) Miller, C. P.; Collini, M. D.; Harris, H. A.; Constrained phytoestrogens and analogues as ERβ sélective ligands. Bioorg. Med. Chem. Lett. 2003, 13, 2399-2403.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 2399-2403
    • Miller, C.P.1    Collini, M.D.2    Harris, H.A.3
  • 17
    • 85081438837 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 0062765, 2000
    • Barlaam, B. C.; Piser, T. M. PCT Int. Appl. WO 0062765, 2000.
    • Barlaam, B.C.1    Piser, T.M.2
  • 18
    • 0035935731 scopus 로고    scopus 로고
    • Estrogen receptor-beta potency-selective ligands: Structure-activity relationship studies of diarylpropionitriles and their acetylene and polar analogues
    • Meyers, M. J.; et al. Estrogen receptor-beta potency-selective ligands: Structure-activity relationship studies of diarylpropionitriles and their acetylene and polar analogues. J. Med. Chem. 2001, 44, 4230-4251.
    • (2001) J. Med. Chem. , vol.44 , pp. 4230-4251
    • Meyers, M.J.1
  • 19
    • 0037312834 scopus 로고    scopus 로고
    • Molecular basis for the subtype discrimination of the estrogen receptor-beta-selective ligand diarylpropionitrile
    • Sun, J.; Baudry, J.; Katzenellenbogen, J. A.; Katzenellenbogen, B. S. Molecular basis for the subtype discrimination of the estrogen receptor-beta-selective ligand diarylpropionitrile. Mol. Endocrinol. 2003, 17, 247-258.
    • (2003) Mol. Endocrinol. , vol.17 , pp. 247-258
    • Sun, J.1    Baudry, J.2    Katzenellenbogen, J.A.3    Katzenellenbogen, B.S.4
  • 20
    • 0023839436 scopus 로고    scopus 로고
    • Estrogen receptor-binding activity of polychlorinated hydroxybiphenyls: Conformationally restricted structural probes
    • (a) Korach, K. S.; Sarver, O.; Chae, K.; McLachlan, J. A.; McKinney, J. D. Estrogen receptor-binding activity of polychlorinated hydroxybiphenyls: conformationally restricted structural probes. Mol. Pharmacol. 1998, 33, 120-126.
    • (1998) Mol. Pharmacol. , vol.33 , pp. 120-126
    • Korach, K.S.1    Sarver, O.2    Chae, K.3    McLachlan, J.A.4    McKinney, J.D.5
  • 21
    • 0038149156 scopus 로고    scopus 로고
    • ER beta ligands. Part 1: The discovery of ER beta selective ligands which embrace the 4-hydroxy-biphenyl template
    • (b) Edsall, R. J.; Harris, H. A.; Manas, E. S.; Mewshaw, R. E. ER beta ligands. Part 1: The discovery of ER beta selective ligands which embrace the 4-hydroxy-biphenyl template. Bioorg. Med. Chem. 2003, 11, 3457-3474.
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 3457-3474
    • Edsall, R.J.1    Harris, H.A.2    Manas, E.S.3    Mewshaw, R.E.4
  • 22
    • 85081434841 scopus 로고    scopus 로고
    • Preparation of benzoxazoles and benzothiazoles as selective ligands for human b-estrogen receptor
    • (Astra-Zeneca AB, Sweden). WO 2002051821, 2002
    • Barlaam, B.; Bernstein, P.; Dantzman, C.; Warwick, P. Preparation of benzoxazoles and benzothiazoles as selective ligands for human b-estrogen receptor. In PCT Int. Appl. 71 pp. (Astra-Zeneca AB, Sweden). WO 2002051821, 2002.
    • PCT Int. Appl.
    • Barlaam, B.1    Bernstein, P.2    Dantzman, C.3    Warwick, P.4
  • 23
    • 85081434368 scopus 로고    scopus 로고
    • Preparation of aminobenzothiazoles as selective ER-β ligands for treatment of Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis or prostate cancer
    • (Astra-Zeneca A. B., Sweden). WO 2003045930, 2003
    • Bernstein, P. Preparation of aminobenzothiazoles as selective ER-β ligands for treatment of Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis or prostate cancer. In PCT Int. Appl. 30 pp. (Astra-Zeneca A. B., Sweden). WO 2003045930, 2003.
    • PCT Int. Appl.
    • Bernstein, P.1
  • 24
    • 0344417000 scopus 로고    scopus 로고
    • Estrogen receptor subtype-selective ligands: Asymmetric synthesis and biological evaluation of cis-and trans-5,11-dialkyl-5,6,11,12- tetrahydrochrysenes
    • Meyers, M. J.; Sun, J.; Carlson, K. E.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Estrogen receptor subtype-selective ligands: Asymmetric synthesis and biological evaluation of cis-and trans-5,11-dialkyl-5,6,11,12- tetrahydrochrysenes. J. Med. Chem. 1999, 42, 2456-2468.
    • (1999) J. Med. Chem. , vol.42 , pp. 2456-2468
    • Meyers, M.J.1    Sun, J.2    Carlson, K.E.3    Katzenellenbogen, B.S.4    Katzenellenbogen, J.A.5
  • 25
    • 0004752110 scopus 로고    scopus 로고
    • Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-alpha or estrogen receptor-beta
    • Sun, J.; et al. Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-alpha or estrogen receptor-beta. Endocrinology 1999, 140, 800-804.
    • (1999) Endocrinology , vol.140 , pp. 800-804
    • Sun, J.1
  • 26
    • 0036234964 scopus 로고    scopus 로고
    • Structural characterization of a subtype-selective ligand reveals a novel mode of estrogen receptor antagonism
    • Shiau, A. K.; et al. Structural characterization of a subtype-selective ligand reveals a novel mode of estrogen receptor antagonism. Nat. Struct. Biol. 2002, 9, 359-64.
    • (2002) Nat. Struct. Biol. , vol.9 , pp. 359-364
    • Shiau, A.K.1
  • 27
    • 0037187189 scopus 로고    scopus 로고
    • Toward selective ER beta Agonists for central nervous system disorders: Synthesis and characterization of aryl benzthiophenes
    • Schopfer, U.; Schoeffter, P.; Bischoff, S. F.; Nozulak, J.; Feuerbach, D.; Floersheim, P. Toward selective ER beta Agonists for central nervous system disorders: Synthesis and characterization of aryl benzthiophenes. J. Med. Chem. 2002, 45, 1399-1401.
    • (2002) J. Med. Chem. , vol.45 , pp. 1399-1401
    • Schopfer, U.1    Schoeffter, P.2    Bischoff, S.F.3    Nozulak, J.4    Feuerbach, D.5    Floersheim, P.6
  • 28
    • 85081438783 scopus 로고    scopus 로고
    • Preparation of nonsteroidal estrogen receptor subtype-selective ligands
    • (Board of Trustees of the University of Illinois). WO 2000019994; 2000
    • Katzenellenbogen, J. A.; et al. Preparation of nonsteroidal estrogen receptor subtype-selective ligands. In PCT Int. Appl., 134 pp. (Board of Trustees of the University of Illinois). WO 2000019994; 2000.
    • PCT Int. Appl.
    • Katzenellenbogen, J.A.1
  • 29
    • 85081439847 scopus 로고    scopus 로고
    • Preparation of substituted isoxazoles as estrogen receptor modulators
    • ((Chiron Corporation, USA). WO 2000008001, 2000)
    • Huebner, V. D.; et al. Preparation of substituted isoxazoles as estrogen receptor modulators. In PCT Int. Appl., 115 pp. ((Chiron Corporation, USA). WO 2000008001, 2000).
    • PCT Int. Appl.
    • Huebner, V.D.1
  • 30
    • 85081436772 scopus 로고    scopus 로고
    • Preparation of benzimidazoles as selective estrogen receptor-b ligand
    • (Astrazeneca AB, Sweden). WO 2002046168; 2002
    • Barlaam, B.; Dock, S.; Folmer, J. Preparation of benzimidazoles as selective estrogen receptor-b ligand. In PCT Int. Appl., 46 pp. (Astrazeneca AB, Sweden). WO 2002046168; 2002.
    • PCT Int. Appl. , pp. 46
    • Barlaam, B.1    Dock, S.2    Folmer, J.3
  • 31
    • 0037028042 scopus 로고    scopus 로고
    • A new series of estrogen receptor modulators that display selectivity for estrogen receptor beta
    • Henke, B. R.; et al. A new series of estrogen receptor modulators that display selectivity for estrogen receptor beta. J. Med. Chem. 2002, 45, 5492-5505.
    • (2002) J. Med. Chem. , vol.45 , pp. 5492-5505
    • Henke, B.R.1
  • 36
    • 84985570392 scopus 로고
    • The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles
    • Stille, J. K. The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
    • (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 508-524
    • Stille, J.K.1
  • 37
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of organoboron compounds
    • Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2483.
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 38
    • 0025977114 scopus 로고
    • Synthesis of fluorinated enynes and dienes via 1-bromo-2-fluoro alkenes
    • Eddarir, S.; Mestdagh, H.; Rolando, C. Synthesis of fluorinated enynes and dienes via 1-bromo-2-fluoro alkenes. Tetrahedron Lett. 1991, 32, 69
    • (1991) Tetrahedron Lett. , vol.32 , pp. 69
    • Eddarir, S.1    Mestdagh, H.2    Rolando, C.3
  • 39
    • 0031562108 scopus 로고    scopus 로고
    • New organometalic reagents using highly reactive metals
    • Rieke, R. D.; Hanosn, M. V. New organometalic reagents using highly reactive metals. Tetrahedron 1997, 53, 1925.
    • (1997) Tetrahedron , vol.53 , pp. 1925
    • Rieke, R.D.1    Hanosn, M.V.2
  • 42
    • 0035106357 scopus 로고    scopus 로고
    • Regulation of metallothionein II messenger ribonucleic acid measures exogenous estrogen receptor-beta activity in SAOS-2 and LNCaPLN3 cells
    • Harris, H. A.; Henderson, R. A.; Bhat, R. A.; Komm, B. S. Regulation of metallothionein II messenger ribonucleic acid measures exogenous estrogen receptor-beta activity in SAOS-2 and LNCaPLN3 cells. Endocrinology 2001, 142, 645-652.
    • (2001) Endocrinology , vol.142 , pp. 645-652
    • Harris, H.A.1    Henderson, R.A.2    Bhat, R.A.3    Komm, B.S.4
  • 44
    • 0036225088 scopus 로고    scopus 로고
    • Estrogen-binding sites and their functional capacity in estrogen receptor double knockout mouse brain
    • Shughrue, P. J.; Askew, G. R.; Dellovade, T. L.; Merchenthaler, I. Estrogen-binding sites and their functional capacity in estrogen receptor double knockout mouse brain. Endocrinology 2002, 143, 1643-1650.
    • (2002) Endocrinology , vol.143 , pp. 1643-1650
    • Shughrue, P.J.1    Askew, G.R.2    Dellovade, T.L.3    Merchenthaler, I.4
  • 45
    • 0031181346 scopus 로고    scopus 로고
    • QXP: Powerful, rapid computer algorithms for structure-based drug design
    • McMartin, C.; Bohacek, R. S. QXP: powerful, rapid computer algorithms for structure-based drug design. J. Comput.-Aided Mol. Design. 1997, 11, 333-44.
    • (1997) J. Comput.-Aided Mol. Design. , vol.11 , pp. 333-344
    • McMartin, C.1    Bohacek, R.S.2
  • 48
    • 0036554817 scopus 로고    scopus 로고
    • Inhibition of androgen-independent growth of prostate cancer xenografts by 17 beta-estradiol
    • (b) Corey, E.; Quinn, J. E.; Emond, M. J.; Buhler, K. R.; Brown, L. G.; Vessella, R. L. Inhibition of androgen-independent growth of prostate cancer xenografts by 17 beta-estradiol. Clin. Cancer Res. 2002, 8, 1003-1007.
    • (2002) Clin. Cancer Res. , vol.8 , pp. 1003-1007
    • Corey, E.1    Quinn, J.E.2    Emond, M.J.3    Buhler, K.R.4    Brown, L.G.5    Vessella, R.L.6
  • 49
    • 0035408472 scopus 로고    scopus 로고
    • Comparative studies of the estrogen receptors beta and alpha and the androgen receptor in normal human prostate glands, dysplasia, and in primary and metastatic carcinoma
    • (c) Leav, I.; Lau, K. M.; Adams, J. Y.; McNeal, J. E.; Taplin, M. E.; Wang, J. F.; Singh, H.; Ho, S. M. Comparative studies of the estrogen receptors beta and alpha and the androgen receptor in normal human prostate glands, dysplasia, and in primary and metastatic carcinoma. Am. J. Pathol. 2001, 259, 79-92.
    • (2001) Am. J. Pathol. , vol.259 , pp. 79-92
    • Leav, I.1    Lau, K.M.2    Adams, J.Y.3    McNeal, J.E.4    Taplin, M.E.5    Wang, J.F.6    Singh, H.7    Ho, S.M.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.