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Volumn 41, Issue 8, 1998, Pages 1272-1283

Synthesis and pharmacology of conformationally restricted raloxifene analogues: Highly potent selective estrogen receptor modulators

Author keywords

[No Author keywords available]

Indexed keywords

2,8 DIHYDROXY [4 [2 (1 PIPERIDINYL)ETHOXY]PHENYL] 5H BENZO[B]NAPTHO[2.1 D]PYRAN; ESTROGEN RECEPTOR; LY 357489; RALOXIFENE; RALOXIFENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 15144355781     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970688z     Document Type: Article
Times cited : (146)

References (60)
  • 1
    • 0002447973 scopus 로고
    • Sex steroids in the pathogenesis and prevention of osteoporosis
    • Riggs, B. L., Melton, L. J., Eds.; Raven: New York
    • Lindsay, R. Sex steroids in the pathogenesis and prevention of osteoporosis. In Osteoporosis: Etiology, Diagnosis, and Management; Riggs, B. L., Melton, L. J., Eds.; Raven: New York, 1988; pp 333-358.
    • (1988) Osteoporosis: Etiology, Diagnosis, and Management , pp. 333-358
    • Lindsay, R.1
  • 2
    • 0001675556 scopus 로고
    • Oestrogen replacement therapy and cardiovascular disease
    • Drife, J. O., Studd, J. W. W., Eds.; Springer-Verlag: London
    • Ross, R. K.; Pike, M. C.; Mack, T. M.; Henderson, B. E. Oestrogen replacement therapy and cardiovascular disease. In HRT and Osteoporosis; Drife, J. O., Studd, J. W. W., Eds.; Springer-Verlag: London, 1990; pp 209-222.
    • (1990) HRT and Osteoporosis , pp. 209-222
    • Ross, R.K.1    Pike, M.C.2    Mack, T.M.3    Henderson, B.E.4
  • 3
    • 0342775106 scopus 로고
    • Oestrogens and cancer
    • Drife, J. O., Studd, J. W. W., Eds.; Springer-Verlag: London
    • Cust, M. P.; Gangar, K. F.; Whitehead, M. I. Oestrogens and cancer. In HRT and Osteoporosis; Drife, J. O., Studd, J. W. W., Eds.; Springer-Verlag: London, 1990; pp 177-186.
    • (1990) HRT and Osteoporosis , pp. 177-186
    • Cust, M.P.1    Gangar, K.F.2    Whitehead, M.I.3
  • 4
    • 0027476353 scopus 로고
    • Current concepts in estrogen replacement therapy in the menopause
    • and references therein
    • Session, D. R.; Kelly, A. C.; Jewelewicz, R. Current concepts in estrogen replacement therapy in the menopause. Fertility Sterility 1993, 2, 277-284 and references therein.
    • (1993) Fertility Sterility , vol.2 , pp. 277-284
    • Session, D.R.1    Kelly, A.C.2    Jewelewicz, R.3
  • 6
    • 0030843969 scopus 로고    scopus 로고
    • (b) Collaborative Group on Hormonal Factors in Breast Cancer. Breast cancer and hormone replacement therapy: Collaborative reanalysis of data from 51 epidemiological studies of 52,705 women with breast cancer and 108,411 women withou breast cancer. Lancet 1997, 350, 1047-1059.
    • (1997) Lancet , vol.350 , pp. 1047-1059
  • 7
    • 0031058448 scopus 로고    scopus 로고
    • Risk of endometrial cancer in relation to use of oestrogen combined with cyclic progestagen therapy in postmenopausal women
    • Beresford, S. A. A.; Weiss, N. S.; Voigt, L. F.; McKnight, B. Risk of endometrial cancer in relation to use of oestrogen combined with cyclic progestagen therapy in postmenopausal women. Lancet 1997, 349, 458-461.
    • (1997) Lancet , vol.349 , pp. 458-461
    • Beresford, S.A.A.1    Weiss, N.S.2    Voigt, L.F.3    McKnight, B.4
  • 8
    • 0023689753 scopus 로고
    • A chemical classification of nonsteroidal antagonists of sex-steroid hormone action
    • For recent reviews, see: (a) Miquel, J.-F.; Gilbert, J. A chemical classification of nonsteroidal antagonists of sex-steroid hormone action. J. Steroid Biochem. Mol. Biol. 1988, 31, 525-544. (b) Magarian, R. A.; Overacre, L. B.; Singh, S.; Meyer, K. L. The medicinal chemistry of nonsteroidal antiestrogens. Curr. Med. Chem. 1994, 1, 61-104. (c) Chander, S. K.; Sahota, S. S.; Evans, T. R. J.; Luqmani, Y. A. The biological evaluation of novel antioestrogens for the treatment of breast cancer. Crit. Rev. Oncol. Hematol. 1993, 15, 243-269. (d) Jordan, V. C. Alternate antiestrogens and approaches to the prevention of breast cancer. J. Cell Biochem. 1995, 51-57.
    • (1988) J. Steroid Biochem. Mol. Biol. , vol.31 , pp. 525-544
    • Miquel, J.-F.1    Gilbert, J.2
  • 9
    • 0028039416 scopus 로고
    • The medicinal chemistry of nonsteroidal antiestrogens
    • For recent reviews, see: (a) Miquel, J.-F.; Gilbert, J. A chemical classification of nonsteroidal antagonists of sex-steroid hormone action. J. Steroid Biochem. Mol. Biol. 1988, 31, 525-544. (b) Magarian, R. A.; Overacre, L. B.; Singh, S.; Meyer, K. L. The medicinal chemistry of nonsteroidal antiestrogens. Curr. Med. Chem. 1994, 1, 61-104. (c) Chander, S. K.; Sahota, S. S.; Evans, T. R. J.; Luqmani, Y. A. The biological evaluation of novel antioestrogens for the treatment of breast cancer. Crit. Rev. Oncol. Hematol. 1993, 15, 243-269. (d) Jordan, V. C. Alternate antiestrogens and approaches to the prevention of breast cancer. J. Cell Biochem. 1995, 51-57.
    • (1994) Curr. Med. Chem. , vol.1 , pp. 61-104
    • Magarian, R.A.1    Overacre, L.B.2    Singh, S.3    Meyer, K.L.4
  • 10
    • 0027761398 scopus 로고
    • The biological evaluation of novel antioestrogens for the treatment of breast cancer
    • For recent reviews, see: (a) Miquel, J.-F.; Gilbert, J. A chemical classification of nonsteroidal antagonists of sex-steroid hormone action. J. Steroid Biochem. Mol. Biol. 1988, 31, 525-544. (b) Magarian, R. A.; Overacre, L. B.; Singh, S.; Meyer, K. L. The medicinal chemistry of nonsteroidal antiestrogens. Curr. Med. Chem. 1994, 1, 61-104. (c) Chander, S. K.; Sahota, S. S.; Evans, T. R. J.; Luqmani, Y. A. The biological evaluation of novel antioestrogens for the treatment of breast cancer. Crit. Rev. Oncol. Hematol. 1993, 15, 243-269. (d) Jordan, V. C. Alternate antiestrogens and approaches to the prevention of breast cancer. J. Cell Biochem. 1995, 51-57.
    • (1993) Crit. Rev. Oncol. Hematol. , vol.15 , pp. 243-269
    • Chander, S.K.1    Sahota, S.S.2    Evans, T.R.J.3    Luqmani, Y.A.4
  • 11
    • 0029451160 scopus 로고
    • Alternate antiestrogens and approaches to the prevention of breast cancer
    • For recent reviews, see: (a) Miquel, J.-F.; Gilbert, J. A chemical classification of nonsteroidal antagonists of sex-steroid hormone action. J. Steroid Biochem. Mol. Biol. 1988, 31, 525-544. (b) Magarian, R. A.; Overacre, L. B.; Singh, S.; Meyer, K. L. The medicinal chemistry of nonsteroidal antiestrogens. Curr. Med. Chem. 1994, 1, 61-104. (c) Chander, S. K.; Sahota, S. S.; Evans, T. R. J.; Luqmani, Y. A. The biological evaluation of novel antioestrogens for the treatment of breast cancer. Crit. Rev. Oncol. Hematol. 1993, 15, 243-269. (d) Jordan, V. C. Alternate antiestrogens and approaches to the prevention of breast cancer. J. Cell Biochem. 1995, 51-57.
    • (1995) J. Cell Biochem. , pp. 51-57
    • Jordan, V.C.1
  • 12
    • 0027172047 scopus 로고
    • A current view of tamoxifen for the treatment and prevention of breast cancer
    • Jordan, V. C. A current view of tamoxifen for the treatment and prevention of breast cancer. Br. J. Pharmacol. 1993, 110, 507-517.
    • (1993) Br. J. Pharmacol. , vol.110 , pp. 507-517
    • Jordan, V.C.1
  • 13
    • 77956727943 scopus 로고    scopus 로고
    • Estrogen receptor modulators: Effects in non-traditional target tissues
    • For recent reviews, see: (a) Grese, T. A.; Dodge, J. A. Estrogen receptor modulators: effects in non-traditional target tissues. Annu. Rep. Med. Chem. 1996, 31, 181-190. (b) Kauffman, R. F.; Bryant, H. U. Selective estrogen receptor modulators. Drug News Perspect. 1995, 8, 531-539. (c) Evans, G. L.; Turner, R. T. Tissue-selective actions of estrogen analogs. Bone 1995, 17, 181S-190S.
    • (1996) Annu. Rep. Med. Chem. , vol.31 , pp. 181-190
    • Grese, T.A.1    Dodge, J.A.2
  • 14
    • 0029560877 scopus 로고
    • Selective estrogen receptor modulators
    • For recent reviews, see: (a) Grese, T. A.; Dodge, J. A. Estrogen receptor modulators: effects in non-traditional target tissues. Annu. Rep. Med. Chem. 1996, 31, 181-190. (b) Kauffman, R. F.; Bryant, H. U. Selective estrogen receptor modulators. Drug News Perspect. 1995, 8, 531-539. (c) Evans, G. L.; Turner, R. T. Tissue-selective actions of estrogen analogs. Bone 1995, 17, 181S-190S.
    • (1995) Drug News Perspect. , vol.8 , pp. 531-539
    • Kauffman, R.F.1    Bryant, H.U.2
  • 15
    • 0028838468 scopus 로고
    • Tissue-selective actions of estrogen analogs
    • For recent reviews, see: (a) Grese, T. A.; Dodge, J. A. Estrogen receptor modulators: effects in non-traditional target tissues. Annu. Rep. Med. Chem. 1996, 31, 181-190. (b) Kauffman, R. F.; Bryant, H. U. Selective estrogen receptor modulators. Drug News Perspect. 1995, 8, 531-539. (c) Evans, G. L.; Turner, R. T. Tissue-selective actions of estrogen analogs. Bone 1995, 17, 181S-190S.
    • (1995) Bone , vol.17
    • Evans, G.L.1    Turner, R.T.2
  • 16
    • 0021201213 scopus 로고
    • Antiestrogens. 2. Structure-activity studies in a series of 3-aroyl-2-arylbenzo[b]thiophene derivatives leading to [6-hydroxy-2-(4-hydroxypnenyl)benzo[&]thien-3-yl]4-[2-(l-piperidinyl)ethoxy] phenyllmethanone hydrochloride (LY156758), a remarkably effective estrogen antagonist with only minimal intrinsic estrogenicity
    • Jones, C. D.; Jevnikar, M. G.; Pike, A. J.; Peters, M. K.; Black, L. J.; Thompson, A. R.; Falcone, J. F.; Clemens, J. A. Antiestrogens. 2. Structure-activity studies in a series of 3-aroyl-2-arylbenzo[b]thiophene derivatives leading to [6-hydroxy-2-(4-hydroxypnenyl)benzo[&]thien-3-yl][4-[2-(l-piperidinyl) ethoxy]phenyllmethanone hydrochloride (LY156758), a remarkably effective estrogen antagonist with only minimal intrinsic estrogenicity. J. Med. Chem. 1984, 27, 1057-1066.
    • (1984) J. Med. Chem. , vol.27 , pp. 1057-1066
    • Jones, C.D.1    Jevnikar, M.G.2    Pike, A.J.3    Peters, M.K.4    Black, L.J.5    Thompson, A.R.6    Falcone, J.F.7    Clemens, J.A.8
  • 17
    • 0030015080 scopus 로고    scopus 로고
    • A controlled trial of raloxifene (LY139481) HCl: Impact on bone turnover and serum lipid profile in healthy postmenopausal women
    • (a) Draper, M. W., Flowers, D. E.; Huster, W. J.; Neild, J. A.; Harper, K. D.; Arnaud, C. A controlled trial of raloxifene (LY139481) HCl: Impact on bone turnover and serum lipid profile in healthy postmenopausal women. J. Bone Miner. Res. 1996, 11, 835-842.
    • (1996) J. Bone Miner. Res. , vol.11 , pp. 835-842
    • Draper, M.W.1    Flowers, D.E.2    Huster, W.J.3    Neild, J.A.4    Harper, K.D.5    Arnaud, C.6
  • 18
    • 0030664688 scopus 로고    scopus 로고
    • Effects of raloxifene on bone mineral density, serum cholesterol concentrations, and uterine endometrium in postmenopausal women
    • (b) Delmas, P. D.; Bjarnason, N. H.; Mitlak, B. H.; Ravoux, A.-C.; Shah, A. S.; Huster, W. J.; Draper, M.; Christiansen, C. Effects of raloxifene on bone mineral density, serum cholesterol concentrations, and uterine endometrium in postmenopausal women. N. Engl. J. Med. 1997, 337, 1641.
    • (1997) N. Engl. J. Med. , vol.337 , pp. 1641
    • Delmas, P.D.1    Bjarnason, N.H.2    Mitlak, B.H.3    Ravoux, A.-C.4    Shah, A.S.5    Huster, W.J.6    Draper, M.7    Christiansen, C.8
  • 19
    • 0029994748 scopus 로고    scopus 로고
    • Raloxifene, tamoxifen, nafoxidine, or estrogen effects on reproductive and nonreproductive tissues in ovariectomized rats
    • (a) Sato, M.; Rippy, M. K.; Bryant, H. U. Raloxifene, tamoxifen, nafoxidine, or estrogen effects on reproductive and nonreproductive tissues in ovariectomized rats. FASEB J. 1996, 10, 905-912.
    • (1996) FASEB J. , vol.10 , pp. 905-912
    • Sato, M.1    Rippy, M.K.2    Bryant, H.U.3
  • 23
    • 0025200714 scopus 로고
    • Structure-activity relationship of antiestrogens. Phenolic analogues of 2,3-diaryl-2H-1-benzopyrans
    • and references therein
    • Sharma, A. P.; Saeed, A.; Durani, S.; Kapil, R. S. Structure-activity relationship of antiestrogens. Phenolic analogues of 2,3-diaryl-2H-1-benzopyrans. J. Med. Chem. 1990, 33, 3222 and references therein.
    • (1990) J. Med. Chem. , vol.33 , pp. 3222
    • Sharma, A.P.1    Saeed, A.2    Durani, S.3    Kapil, R.S.4
  • 24
    • 0029876149 scopus 로고    scopus 로고
    • Benzopyran selective estrogen receptor modulators (SERMs): Pharmacological effects and structural correlation with raloxifene
    • Grese, T. A.; Sluka, J. P.; Bryant, H. U.; Cole, H. W.; Kim, J. R.; Magee, D. E.; Rowley, E. R.; Sato, M. Benzopyran selective estrogen receptor modulators (SERMs): pharmacological effects and structural correlation with raloxifene. Bioorg. Med. Chem. Lett. 1996, 6, 903-908.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 903-908
    • Grese, T.A.1    Sluka, J.P.2    Bryant, H.U.3    Cole, H.W.4    Kim, J.R.5    Magee, D.E.6    Rowley, E.R.7    Sato, M.8
  • 25
    • 0041537827 scopus 로고    scopus 로고
    • Stochastic approach to force field evaluations: Conformational analysis of raloxifene, a potential new therapeutic agent for post-menopausal osteoporosis
    • (a) Boyd, D. B.; Coner, R. D. Stochastic approach to force field evaluations: conformational analysis of raloxifene, a potential new therapeutic agent for post-menopausal osteoporosis. J. Mol. Struct. (THEOCHEM) 1996, 368, 7-15.
    • (1996) J. Mol. Struct. (THEOCHEM) , vol.368 , pp. 7-15
    • Boyd, D.B.1    Coner, R.D.2
  • 26
    • 0027143193 scopus 로고
    • Molecular structures, conformation analysis, and preferential modes of binding of 3-aroyl-2-arylbenzo[b]thiophene estrogen receptor ligands: LY117018 and aryl aside photoaffinity labeling analogs
    • (b) Kym, P. R.; Anstead, G. M.; Pinney, K. G.; Wilson, S. R.; Katzenellenbogen, J. A. Molecular structures, conformation analysis, and preferential modes of binding of 3-aroyl-2-arylbenzo[b]thiophene estrogen receptor ligands: LY117018 and aryl aside photoaffinity labeling analogs. J. Med. Chem. 1993, 36, 3910-3922.
    • (1993) J. Med. Chem. , vol.36 , pp. 3910-3922
    • Kym, P.R.1    Anstead, G.M.2    Pinney, K.G.3    Wilson, S.R.4    Katzenellenbogen, J.A.5
  • 29
    • 84920313391 scopus 로고    scopus 로고
    • note
    • 20 command line options of AM1 GRADIENT POLAR GEO-OK HESS=1 EF GNORM=0.01SCFCRT=1D-12 MMOK PRECISE NOINTER and GRAPH. Least squares superimpositions of the stilbene cores were performed using the Insight-II version 95.0.4 (Molecular Simulations Inc., San Diego, CA).
  • 30
    • 84920313390 scopus 로고    scopus 로고
    • Research Laboratory, U.S. Air Force Academy, CO 90940
    • and references therein
    • By James P. Stewart, Frank J. Seller, Research Laboratory, U.S. Air Force Academy, CO 90940. QCPE No. 455 and references therein.
    • QCPE No. 455 , vol.455
    • Stewart, J.P.1    Seller, F.J.2
  • 31
    • 0028865401 scopus 로고
    • Novel methodology for the synthesis of estrogenic and antiestrogenic isoflav-3-enes
    • Grese, T. A.; Pennington, L. D. Novel methodology for the synthesis of estrogenic and antiestrogenic isoflav-3-enes. Tetrahedron Lett. 1995, 36, 8913-8916.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8913-8916
    • Grese, T.A.1    Pennington, L.D.2
  • 32
    • 0030593866 scopus 로고    scopus 로고
    • Conversion of the phytoestrogen coumestrol into a selective estrogen receptor modulator (SERM) by attachment of an amine-containing side chain
    • A portion of this work has previously appeared in communication form: Grese, T. A.; Cole, H. W.; Magee, D. E.; Phillips, D. L.; Shetler, P. K.; Short, L. L.; Glasebrook, A. L.; Bryant, H. U. Conversion of the phytoestrogen coumestrol into a selective estrogen receptor modulator (SERM) by attachment of an amine-containing side chain. Bioorg, Med. Chem. Lett. 1996, 6, 2683-2686.
    • (1996) Bioorg, Med. Chem. Lett. , vol.6 , pp. 2683-2686
    • Grese, T.A.1    Cole, H.W.2    Magee, D.E.3    Phillips, D.L.4    Shetler, P.K.5    Short, L.L.6    Glasebrook, A.L.7    Bryant, H.U.8
  • 33
    • 0000474341 scopus 로고
    • Thianaphthen-2-one chemistry. I. Synthesis of 6H-benzothieno[3,2-c][1]benzopyran-6-ones (11thiacoumestans)
    • Conley, R. A.; Heindel, N. D. Thianaphthen-2-one chemistry. I. Synthesis of 6H-benzothieno[3,2-c][1]benzopyran-6-ones (11thiacoumestans). J. Org. Chem. 1975, 40, 3169-3173.
    • (1975) J. Org. Chem. , vol.40 , pp. 3169-3173
    • Conley, R.A.1    Heindel, N.D.2
  • 34
    • 0001560775 scopus 로고
    • Destabilized carbocations. Nuclear magnetic resonance detection and reactivities of aryl α-thioformamidyl cations
    • Ablenas, F. J.; George, B. E.; Maleki, M.; Jain, R.; Hopkinson, A. C.; Lee-Ruff, E. Destabilized carbocations. Nuclear magnetic resonance detection and reactivities of aryl α-thioformamidyl cations. Can. J. Chem. 1987, 65, 1800-1803.
    • (1987) Can. J. Chem. , vol.65 , pp. 1800-1803
    • Ablenas, F.J.1    George, B.E.2    Maleki, M.3    Jain, R.4    Hopkinson, A.C.5    Lee-Ruff, E.6
  • 35
    • 84920313389 scopus 로고    scopus 로고
    • unpublished results
    • Schmid, C. R., unpublished results.
    • Schmid, C.R.1
  • 36
    • 0000822189 scopus 로고
    • Synthesis of two benzothiacyclanones via a novel two-carbon ring expansion of thiolactones with vinyllithium
    • Lumma, W. C., Jr.; Dutra, G. A.; Voekker, C. A. Synthesis of two benzothiacyclanones via a novel two-carbon ring expansion of thiolactones with vinyllithium. J. Org. Chem. 1970, 35, 3442-3444.
    • (1970) J. Org. Chem. , vol.35 , pp. 3442-3444
    • Lumma Jr., W.C.1    Dutra, G.A.2    Voekker, C.A.3
  • 37
    • 84920320033 scopus 로고
    • Selective carboalkoxylation of 6-methoxy-2-tetralone
    • Colvin, E. W.; Martin, J.; Shroot, B. Selective carboalkoxylation of 6-methoxy-2-tetralone. Chem. Ind. (London) 1966, 2130.
    • (1966) Chem. Ind. (London) , pp. 2130
    • Colvin, E.W.1    Martin, J.2    Shroot, B.3
  • 38
    • 0002091136 scopus 로고
    • The Pechman reaction
    • Sethna, S.; Phadke, R. The Pechman reaction. Org. React. 1953, 7, 1-58.
    • (1953) Org. React. , vol.7 , pp. 1-58
    • Sethna, S.1    Phadke, R.2
  • 39
    • 9544250693 scopus 로고
    • Utility of 4-trimethylsiloxyphenylmagnesium bromide in Grignard reactions
    • Bindal, R. D.; Durani, S.; Kapil, R. S.; Anand, N. Utility of 4-trimethylsiloxyphenylmagnesium bromide in Grignard reactions. Synthesis 1982, 405.
    • (1982) Synthesis , pp. 405
    • Bindal, R.D.1    Durani, S.2    Kapil, R.S.3    Anand, N.4
  • 40
    • 0000030576 scopus 로고
    • Multiple binding sites for the anti-estrogen raloxifene (LY156758)
    • Glasebrook, A. L.; Phillips, D. L.; Sluka, J. P. Multiple binding sites for the anti-estrogen raloxifene (LY156758). J. Bone Miner. Res. 1993, 8 (Suppl. 1), S268. Scholl, S. M.; Huff, K. K.; Lippman, M. E. Antiestrogenic effects of LY117018 in MCF-7 cells. Endocrinology 1983, 113, 611-617. Miller, M. A.; Katzenellenbogen, B. S. Characterization and quantitation of antiestrogen binding sites in estrogen receptor-positive and -negative human breast cancer cell lines. Cancer Res. 1983, 43, 3094-3100.
    • (1993) J. Bone Miner. Res. , vol.8 , Issue.SUPPL. 1
    • Glasebrook, A.L.1    Phillips, D.L.2    Sluka, J.P.3
  • 41
    • 0020516248 scopus 로고
    • Antiestrogenic effects of LY117018 in MCF-7 cells
    • Glasebrook, A. L.; Phillips, D. L.; Sluka, J. P. Multiple binding sites for the anti-estrogen raloxifene (LY156758). J. Bone Miner. Res. 1993, 8 (Suppl. 1), S268. Scholl, S. M.; Huff, K. K.; Lippman, M. E. Antiestrogenic effects of LY117018 in MCF-7 cells. Endocrinology 1983, 113, 611-617. Miller, M. A.; Katzenellenbogen, B. S. Characterization and quantitation of antiestrogen binding sites in estrogen receptor-positive and -negative human breast cancer cell lines. Cancer Res. 1983, 43, 3094-3100.
    • (1983) Endocrinology , vol.113 , pp. 611-617
    • Scholl, S.M.1    Huff, K.K.2    Lippman, M.E.3
  • 42
    • 0020569987 scopus 로고
    • Characterization and quantitation of antiestrogen binding sites in estrogen receptor-positive and -negative human breast cancer cell lines
    • Glasebrook, A. L.; Phillips, D. L.; Sluka, J. P. Multiple binding sites for the anti-estrogen raloxifene (LY156758). J. Bone Miner. Res. 1993, 8 (Suppl. 1), S268. Scholl, S. M.; Huff, K. K.; Lippman, M. E. Antiestrogenic effects of LY117018 in MCF-7 cells. Endocrinology 1983, 113, 611-617. Miller, M. A.; Katzenellenbogen, B. S. Characterization and quantitation of antiestrogen binding sites in estrogen receptor-positive and -negative human breast cancer cell lines. Cancer Res. 1983, 43, 3094-3100.
    • (1983) Cancer Res. , vol.43 , pp. 3094-3100
    • Miller, M.A.1    Katzenellenbogen, B.S.2
  • 44
    • 0343209783 scopus 로고
    • Pharmacologic profile of estrogen-induced uterine eosiophilia in the ovariectomized (OVX) rat
    • Bryant, H. U.; Bendele, A. M.; Magee, D. E.; Cole, H. W.; Spaethe, S. W. Pharmacologic profile of estrogen-induced uterine eosiophilia in the ovariectomized (OVX) rat. Pharmacologist 1992, 34, 194.
    • (1992) Pharmacologist , vol.34 , pp. 194
    • Bryant, H.U.1    Bendele, A.M.2    Magee, D.E.3    Cole, H.W.4    Spaethe, S.W.5
  • 45
    • 0002081094 scopus 로고
    • The ovariectomized rat as an animal model for postmenopausal bone loss
    • Wronski, T. J.; Yen, C.-F. The ovariectomized rat as an animal model for postmenopausal bone loss. Cells Mater. 1991, Suppl 1, 69.
    • (1991) Cells Mater. , Issue.SUPPL. 1 , pp. 69
    • Wronski, T.J.1    Yen, C.-F.2
  • 46
    • 0001883015 scopus 로고
    • Raloxifene is a tissue specific anti-estrogen that blocks tamoxifen or estrogen-stimulated uterotrophic effects
    • (a) Fuchs-Young, R.; Magee, D. E.; Cole, H. W.; Short, L.; Glasebrook, A. L.; Rippy, M. K.; Termine, J. D.; Bryant, H. U. Raloxifene is a tissue specific anti-estrogen that blocks tamoxifen or estrogen-stimulated uterotrophic effects. Endocrinology 1995, 135 (Suppl.), 57.
    • (1995) Endocrinology , vol.135 , Issue.SUPPL. , pp. 57
    • Fuchs-Young, R.1    Magee, D.E.2    Cole, H.W.3    Short, L.4    Glasebrook, A.L.5    Rippy, M.K.6    Termine, J.D.7    Bryant, H.U.8
  • 49
    • 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 1997, 62, 268-303.
    • (1997) Steroids , vol.62 , pp. 268-303
    • Anstead, G.M.1    Carlson, K.E.2    Katzenellenbogen, J.A.3
  • 51
    • 0020067155 scopus 로고
    • On the other hand, in the tamoxifen series, substitution of the dimethylamino group by piperidine does not result in a reduction of uterine stimulation: Robertson, D. W.; Katzenellenbogen, J. A.; Hayes, J. R.; Katzenellenbogen, B. S. J. Med. Chem. 1982, 25, 167-171. Therefore, the presence of cyclic amino functionality appears to be necessary but not sufficient to achieve slectivity with respect to uterine effects (ref 18).
    • (1982) J. Med. Chem. , vol.25 , pp. 167-171
    • Robertson, D.W.1    Katzenellenbogen, J.A.2    Hayes, J.R.3    Katzenellenbogen, B.S.4
  • 53
    • 0030987014 scopus 로고    scopus 로고
    • Synthesis and estrogen receptor binding affinities of the major human metabolites of raloxifene (LY139481)
    • and references therein
    • Dodge, J. A.; Lugar, C. W.; Cho, S.; Osborne, J. J.; Phillips, D. L.; Glasebrook, A. L.; Frolik, C. A. Synthesis and estrogen receptor binding affinities of the major human metabolites of raloxifene (LY139481). Bioorg. Med. Chem. Lett. 1997, 7, 993-996, and references therein.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 993-996
    • Dodge, J.A.1    Lugar, C.W.2    Cho, S.3    Osborne, J.J.4    Phillips, D.L.5    Glasebrook, A.L.6    Frolik, C.A.7
  • 54
    • 0029038986 scopus 로고
    • Analysis of estrogen receptor function in vitro reveals three distinct classes of antiestrogens
    • (a) McDonnell, D. P.; Clemm, D. L.; Hermann, T.; Goldman, M. E.; Pike, J. W. Analysis of estrogen receptor function in vitro reveals three distinct classes of antiestrogens. Mol. Endocrinol. 1995, 9, 659-669.
    • (1995) Mol. Endocrinol. , vol.9 , pp. 659-669
    • McDonnell, D.P.1    Clemm, D.L.2    Hermann, T.3    Goldman, M.E.4    Pike, J.W.5
  • 55
    • 0029994081 scopus 로고    scopus 로고
    • Site-directed estrogen receptor antibodies stabilize 4-hydroxytamoxifen ligand, but not estradiol, and indicate ligand-specific differences in the recognition of estrogen response element DNA in vitro
    • (b) Klinge, C. M.; Traish, A. M.; Driscoll, M. D.; Hilf, R.; Bambara, R. A. Site-directed estrogen receptor antibodies stabilize 4-hydroxytamoxifen ligand, but not estradiol, and indicate ligand-specific differences in the recognition of estrogen response element DNA in vitro. Steroids 1996, 61, 278-289.
    • (1996) Steroids , vol.61 , pp. 278-289
    • Klinge, C.M.1    Traish, A.M.2    Driscoll, M.D.3    Hilf, R.4    Bambara, R.A.5
  • 56
    • 0030071445 scopus 로고    scopus 로고
    • Tripartite steroid hormone receptor pharmacology: Interaction with multiple effector sites as a basis for the cell- And promoter-specific action of these hormones
    • For a detailed description of the current understanding of tissue-specific steroid hormone activities, see: Katzenellenbogen, J. A.; O'Malley, B. W.; Katzenellenbogen, B. S. Tripartite steroid hormone receptor pharmacology: Interaction with multiple effector sites as a basis for the cell- and promoter-specific action of these hormones. Mol. Endocrinol. 1996, 10, 119-131.
    • (1996) Mol. Endocrinol. , vol.10 , pp. 119-131
    • Katzenellenbogen, J.A.1    O'Malley, B.W.2    Katzenellenbogen, B.S.3
  • 57
    • 0029841146 scopus 로고    scopus 로고
    • Identification of an estrogen response element activated by metabolites of 17β-estradiol and raloxifene
    • (a) Yang, N. N.; Venugopalan, M.; Hardikar, S.; Glasebrook, A. G. Identification of an estrogen response element activated by metabolites of 17β-estradiol and raloxifene. Science 1996, 273, 1222-1225.
    • (1996) Science , vol.273 , pp. 1222-1225
    • Yang, N.N.1    Venugopalan, M.2    Hardikar, S.3    Glasebrook, A.G.4
  • 58
    • 0029961569 scopus 로고    scopus 로고
    • Estrogen and raloxifene stimulate transforming growth factor-β3 gene expression in rat bone: A potential mechanism for estrogen- Or raloxifene-mediated bone maintenance
    • (b) Yang, N. N.; Bryant, H. U.; Hardikar, S.; Sato, M.; Galvin, R. J. S.; Glasebrook, A. L.; Termine, J. D. Estrogen and raloxifene stimulate transforming growth factor-β3 gene expression in rat bone: a potential mechanism for estrogen- or raloxifene-mediated bone maintenance. Endocrinology 1996, 137, 2075-2084.
    • (1996) Endocrinology , vol.137 , pp. 2075-2084
    • Yang, N.N.1    Bryant, H.U.2    Hardikar, S.3    Sato, M.4    Galvin, R.J.S.5    Glasebrook, A.L.6    Termine, J.D.7
  • 59
    • 0022553965 scopus 로고
    • Studies in antifertility agents. 50: Stereoselective binding of d- And l-centchromans to estrogen receptors and their antifertility activity
    • Salman, M.; Ray, S.; Anand, N.; Agarwal, A. K.; Singh, M. M.; Setty, B. S.; Kamboj, V. P. Studies in antifertility agents. 50: Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity. J. Med. Chem. 1986, 29, 1801-1803.
    • (1986) J. Med. Chem. , vol.29 , pp. 1801-1803
    • Salman, M.1    Ray, S.2    Anand, N.3    Agarwal, A.K.4    Singh, M.M.5    Setty, B.S.6    Kamboj, V.P.7


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