메뉴 건너뛰기




Volumn 57, Issue 8, 2014, Pages 3532-3545

Triaryl-substituted schiff bases are high-affinity subtype-selective ligands for the estrogen receptor

Author keywords

[No Author keywords available]

Indexed keywords

4,4' [(2 TOLYLIMINO)METHYLENE]DIPHENOL; 4,4' [(3 TOLYLIMINO)METHYLENE]DIPHENOL; 4,4' [(4 TOLYLIMINO)METHYLENE]DIPHENOL; 4,4' [(PHENYLIMINO)METHYLENE]DIPHENOL; 4,4' [[(2 CHLOROPHENYL)IMINO]METHYLENE]DIPHENOL; 4,4' [[(2,6 DIMETHYLPHENYL)IMINO]METHYLENE]DIPHENOL; 4,4' [[(3 CHLOROPHENYL)IMINO]METHYLENE]DIPHENOL; 4,4' [[(4 BROMOPHENYL)IMINO]METHYLENE]DIPHENOL; 4,4' [[(4 CHLOROPHENYL)IMINO]METHYLENE]DIPHENOL; 4,4' [[(4 FLUOROPHENYL)IMINO]METHYLENE]DIPHENOL; 4,4' [[(4 HYDROXYPHENYL)IMINO]METHYLENE]DIPHENOL; 4,4' [[(4 METHOXYPHENYL)IMINO]METHYLENE]DIPHENOL; 4,4' [[[3 (TRIFLUOROMETHYL)PHENYL]IMINO]METHYLENE]DIPHENOL; ANILINE DERIVATIVE; BENZOPHENONE DERIVATIVE; IMINE; LIGAND; SCHIFF BASE; SELECTIVE ESTROGEN RECEPTOR MODULATOR; UNCLASSIFIED DRUG;

EID: 84899584090     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm500268j     Document Type: Article
Times cited : (24)

References (46)
  • 1
    • 80053508317 scopus 로고    scopus 로고
    • The 2010 Philip S. Portoghese Medicinal Chemistry Lectureship: Addressing the "core issue" in the design of estrogen receptor ligands
    • Katzenellenbogen, J. A. The 2010 Philip S. Portoghese Medicinal Chemistry Lectureship: Addressing the "core issue" in the design of estrogen receptor ligands J. Med. Chem. 2011, 54, 5271-5282
    • (2011) J. Med. Chem. , vol.54 , pp. 5271-5282
    • Katzenellenbogen, J.A.1
  • 3
    • 0034086636 scopus 로고    scopus 로고
    • Acyclic amides as estrogen receptor ligands: Synthesis, binding, activity and receptor interaction
    • Stauffer, S. R.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Acyclic amides as estrogen receptor ligands: Synthesis, binding, activity and receptor interaction Bioorg. Med. Chem. 2000, 8, 1293-1316
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 1293-1316
    • Stauffer, S.R.1    Sun, J.2    Katzenellenbogen, B.S.3    Katzenellenbogen, J.A.4
  • 4
    • 0033117680 scopus 로고    scopus 로고
    • Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens
    • Fink, B. E.; Mortensen, D. S.; Stauffer, S. R.; Aron, Z. D.; Katzenellenbogen, J. A. Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens Chem. Biol. 1999, 6, 205-219
    • (1999) Chem. Biol. , vol.6 , pp. 205-219
    • Fink, B.E.1    Mortensen, D.S.2    Stauffer, S.R.3    Aron, Z.D.4    Katzenellenbogen, J.A.5
  • 7
    • 84867548237 scopus 로고    scopus 로고
    • Bicyclic core estrogens as full antagonists: Synthesis, biological evaluation and structure-activity relationships of estrogen receptor ligands based on bridged oxabicyclic core arylsulfonamides
    • Zhu, M.; Zhang, C.; Nwachukwu, J. C.; Srinivasan, S.; Cavett, V.; Zheng, Y.; Carlson, K. E.; Dong, C.; Katzenellenbogen, J. A.; Nettles, K. W.; Zhou, H. B. Bicyclic core estrogens as full antagonists: Synthesis, biological evaluation and structure-activity relationships of estrogen receptor ligands based on bridged oxabicyclic core arylsulfonamides Org. Biomol. Chem. 2012, 10, 8692-8700
    • (2012) Org. Biomol. Chem. , vol.10 , pp. 8692-8700
    • Zhu, M.1    Zhang, C.2    Nwachukwu, J.C.3    Srinivasan, S.4    Cavett, V.5    Zheng, Y.6    Carlson, K.E.7    Dong, C.8    Katzenellenbogen, J.A.9    Nettles, K.W.10    Zhou, H.B.11
  • 9
    • 80053562371 scopus 로고    scopus 로고
    • Development of subtype-selective oestrogen receptor-based therapeutics
    • Nilsson, S.; Koehler, K. F.; Gustafsson, J. A. Development of subtype-selective oestrogen receptor-based therapeutics Nat. Rev. Drug Discovery 2011, 10, 778-792
    • (2011) Nat. Rev. Drug Discovery , vol.10 , pp. 778-792
    • Nilsson, S.1    Koehler, K.F.2    Gustafsson, J.A.3
  • 10
    • 78149501152 scopus 로고    scopus 로고
    • The molecular mechanisms underlying the pharmacological actions of ER modulators: Implications for new drug discovery in breast cancer
    • McDonnell, D. P.; Wardell, S. E. The molecular mechanisms underlying the pharmacological actions of ER modulators: Implications for new drug discovery in breast cancer Curr. Opin. Pharmacol. 2010, 10, 620-628
    • (2010) Curr. Opin. Pharmacol. , vol.10 , pp. 620-628
    • McDonnell, D.P.1    Wardell, S.E.2
  • 11
    • 0036744793 scopus 로고    scopus 로고
    • Selective estrogen receptor modulators
    • Bryant, H. U. Selective estrogen receptor modulators Rev. Endocr. Metab. Disord. 2002, 3, 231-241
    • (2002) Rev. Endocr. Metab. Disord. , vol.3 , pp. 231-241
    • Bryant, H.U.1
  • 12
    • 79955788943 scopus 로고    scopus 로고
    • An ADIOL-ERbeta-CtBP transrepression pathway negatively regulates microglia-mediated inflammation
    • Saijo, K.; Collier, J. G.; Li, A. C.; Katzenellenbogen, J. A.; Glass, C. K. An ADIOL-ERbeta-CtBP transrepression pathway negatively regulates microglia-mediated inflammation Cell 2011, 145, 584-595
    • (2011) Cell , vol.145 , pp. 584-595
    • Saijo, K.1    Collier, J.G.2    Li, A.C.3    Katzenellenbogen, J.A.4    Glass, C.K.5
  • 14
    • 84899510780 scopus 로고
    • Molecular structure and estrogenic activity of methylenimine derivatives. II
    • Nomura, Y. Molecular structure and estrogenic activity of methylenimine derivatives. II Nippon Kagaku Zasshi 1956, 77, 1072-1074
    • (1956) Nippon Kagaku Zasshi , vol.77 , pp. 1072-1074
    • Nomura, Y.1
  • 15
    • 84899561855 scopus 로고
    • Molecular structure and estrogenic activity of methylenimine derivatives. III
    • Nomura, Y. Molecular structure and estrogenic activity of methylenimine derivatives. III Nippon Kagaku Zasshi 1956, 77, 1074-1075
    • (1956) Nippon Kagaku Zasshi , vol.77 , pp. 1074-1075
    • Nomura, Y.1
  • 17
    • 37249091614 scopus 로고    scopus 로고
    • Divergent approach for synthesis and terminal modifications of dendritic polyphenylazomethines
    • Takanashi, K.; Yamamoto, K. Divergent approach for synthesis and terminal modifications of dendritic polyphenylazomethines Org. Lett. 2007, 9, 5151-5154
    • (2007) Org. Lett. , vol.9 , pp. 5151-5154
    • Takanashi, K.1    Yamamoto, K.2
  • 18
    • 0030734795 scopus 로고    scopus 로고
    • Altered ligand binding properties and enhanced stability of a constitutively 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 constitutively active estrogen receptor: Evidence that an open pocket conformation is required for ligand interaction Biochemistry 1997, 36, 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
  • 19
    • 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
  • 20
    • 0024424089 scopus 로고
    • 2-Arylindenes and 2-arylindenones: Molecular structures and considerations in the binding orientation of unsymmetrical nonsteroidal ligands to the estrogen receptor
    • Anstead, G. M.; Wilson, S. R.; Katzenellenbogen, J. A. 2-Arylindenes and 2-arylindenones: Molecular structures and considerations in the binding orientation of unsymmetrical nonsteroidal ligands to the estrogen receptor J. Med. Chem. 1989, 32, 2163-2171
    • (1989) J. Med. Chem. , vol.32 , pp. 2163-2171
    • Anstead, G.M.1    Wilson, S.R.2    Katzenellenbogen, J.A.3
  • 22
    • 0032976793 scopus 로고    scopus 로고
    • A comparison of transcriptional activation by ER alpha and ER beta
    • Cowley, S. M.; Parker, M. G. A comparison of transcriptional activation by ER alpha and ER beta J. Steroid Biochem. Mol. Biol. 1999, 69, 165-175
    • (1999) J. Steroid Biochem. Mol. Biol. , vol.69 , pp. 165-175
    • Cowley, S.M.1    Parker, M.G.2
  • 23
    • 0037077233 scopus 로고    scopus 로고
    • Interaction of transcriptional intermediary factor 2 nuclear receptor box peptides with the coactivator binding site of estrogen receptor alpha
    • Warnmark, A.; Treuter, E.; Gustafsson, J. A.; Hubbard, R. E.; Brzozowski, A. M.; Pike, A. C. Interaction of transcriptional intermediary factor 2 nuclear receptor box peptides with the coactivator binding site of estrogen receptor alpha J. Biol. Chem. 2002, 277, 21862-21868
    • (2002) J. Biol. Chem. , vol.277 , pp. 21862-21868
    • Warnmark, A.1    Treuter, E.2    Gustafsson, J.A.3    Hubbard, R.E.4    Brzozowski, A.M.5    Pike, A.C.6
  • 25
    • 0032446607 scopus 로고    scopus 로고
    • The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen
    • Shiau, A. K.; Barstad, D.; Loria, P. M.; Cheng, L.; Kushner, P. J.; Agard, D. A.; Greene, G. L. The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen Cell 1998, 95, 927-937
    • (1998) Cell , vol.95 , pp. 927-937
    • Shiau, A.K.1    Barstad, D.2    Loria, P.M.3    Cheng, L.4    Kushner, P.J.5    Agard, D.A.6    Greene, G.L.7
  • 26
    • 0028809776 scopus 로고
    • The structural pervasiveness of estrogenic activity
    • Katzenellenbogen, J. A. The structural pervasiveness of estrogenic activity Environ. Health Perspect. 1995, 103, 99-101
    • (1995) Environ. Health Perspect. , vol.103 , pp. 99-101
    • Katzenellenbogen, J.A.1
  • 27
    • 0346504253 scopus 로고    scopus 로고
    • Interactions of exogenous endocrine active substances with nuclear receptors
    • Katzenellenbogen, J. A.; Muthyala, R. S. Interactions of exogenous endocrine active substances with nuclear receptors Pure Appl. Chem. 2003, 75, 1797-1817
    • (2003) Pure Appl. Chem. , vol.75 , pp. 1797-1817
    • Katzenellenbogen, J.A.1    Muthyala, R.S.2
  • 28
    • 51349148740 scopus 로고    scopus 로고
    • Promising core structure for nuclear receptor ligands: Design and synthesis of novel estrogen receptor ligands based on diphenylamine skeleton
    • Ohta, K.; Chiba, Y.; Ogawa, T.; Endo, Y. Promising core structure for nuclear receptor ligands: Design and synthesis of novel estrogen receptor ligands based on diphenylamine skeleton Bioorg. Med. Chem. Lett. 2008, 18, 5050-5053
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 5050-5053
    • Ohta, K.1    Chiba, Y.2    Ogawa, T.3    Endo, Y.4
  • 30
    • 0037375029 scopus 로고    scopus 로고
    • Synthesis, binding affinity, and transcriptional activity of hydroxy- and methoxy-substituted 3,4-diarylsalicylaldoximes on estrogen receptors alpha and beta
    • Minutolo, F.; Antonello, M.; Bertini, S.; Rapposelli, S.; Rossello, A.; Sheng, S. B.; Carlson, K. E.; Katzenellenbogen, J. A.; Macchia, M. Synthesis, binding affinity, and transcriptional activity of hydroxy- and methoxy-substituted 3,4-diarylsalicylaldoximes on estrogen receptors alpha and beta Bioorg. Med. Chem. 2003, 11, 1247-1257
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 1247-1257
    • Minutolo, F.1    Antonello, M.2    Bertini, S.3    Rapposelli, S.4    Rossello, A.5    Sheng, S.B.6    Carlson, K.E.7    Katzenellenbogen, J.A.8    MacChia, M.9
  • 36
    • 36448985603 scopus 로고    scopus 로고
    • Estrogen and tumors: For better or for worse?
    • author reply pp 1239-1240 - 1240
    • van der Windt, D. J.; Kok, N. F.; Ijzermans, J. Estrogen and tumors: For better or for worse? Science 2007, 318, 1239-1240; author reply pp 1239-1240
    • (2007) Science , vol.318 , pp. 1239
    • Van Der Windt, D.J.1    Kok, N.F.2    Ijzermans, J.3
  • 37
    • 38649140488 scopus 로고    scopus 로고
    • The role of estrogens and estrogen receptors in normal prostate growth and disease
    • Prins, G. S.; Korach, K. S. The role of estrogens and estrogen receptors in normal prostate growth and disease Steroids 2008, 73, 233-244
    • (2008) Steroids , vol.73 , pp. 233-244
    • Prins, G.S.1    Korach, K.S.2
  • 38
    • 1542319924 scopus 로고    scopus 로고
    • Equol, a natural estrogenic metabolite from soy isoflavones: Convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta
    • Muthyala, R. S.; Ju, Y. H.; Sheng, S.; Williams, L. D.; Doerge, D. R.; Katzenellenbogen, B. S.; Helferich, W. G.; Katzenellenbogen, J. A. Equol, a natural estrogenic metabolite from soy isoflavones: Convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta Bioorg. Med. Chem. 2004, 12, 1559-1567
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 1559-1567
    • Muthyala, R.S.1    Ju, Y.H.2    Sheng, S.3    Williams, L.D.4    Doerge, D.R.5    Katzenellenbogen, B.S.6    Helferich, W.G.7    Katzenellenbogen, J.A.8
  • 39
    • 0018749247 scopus 로고
    • Zearalenones: Characterization of the estrogenic potencies and receptor interactions of a series of fungal beta-resorcylic acid lactones
    • Katzenellenbogen, B. S.; Katzenellenbogen, J. A.; Mordecai, D. Zearalenones: Characterization of the estrogenic potencies and receptor interactions of a series of fungal beta-resorcylic acid lactones Endocrinology 1979, 105, 33-40
    • (1979) Endocrinology , vol.105 , pp. 33-40
    • Katzenellenbogen, B.S.1    Katzenellenbogen, J.A.2    Mordecai, D.3
  • 40
    • 0037153283 scopus 로고    scopus 로고
    • Investigations on estrogen receptor binding. The estrogenic, antiestrogenic, and cytotoxic properties of C2-alkyl-substituted 1,1-bis(4-hydroxyphenyl)-2-phenylethenes
    • Lubczyk, V.; Bachmann, H.; Gust, R. Investigations on estrogen receptor binding. The estrogenic, antiestrogenic, and cytotoxic properties of C2-alkyl-substituted 1,1-bis(4-hydroxyphenyl)-2-phenylethenes J. Med. Chem. 2002, 45, 5358-5364
    • (2002) J. Med. Chem. , vol.45 , pp. 5358-5364
    • Lubczyk, V.1    Bachmann, H.2    Gust, R.3
  • 41
    • 84899571662 scopus 로고
    • The estrogenic azo compounds
    • Takahashi, T. The estrogenic azo compounds Nippon Kagaku Kaishi 1953, 74, 673-675
    • (1953) Nippon Kagaku Kaishi , vol.74 , pp. 673-675
    • Takahashi, T.1
  • 42
    • 84899530366 scopus 로고
    • 2,2′,4,4′-Tetrahydroxyazobenzene a synthetic estrogen of a new type
    • Urushibara, Y.; Takahashi, T. 2,2′,4,4′- Tetrahydroxyazobenzene a synthetic estrogen of a new type Bull. Chem. Soc. Jpn. 1953, 26, 62-63
    • (1953) Bull. Chem. Soc. Jpn. , vol.26 , pp. 62-63
    • Urushibara, Y.1    Takahashi, T.2
  • 44
    • 84861559154 scopus 로고    scopus 로고
    • Development of selective estrogen receptor modulator (SERM)-like activity through an indirect mechanism of estrogen receptor antagonism: Defining the binding mode of 7-oxabicyclo[2.2.1]hept-5-ene scaffold core ligands
    • Zheng, Y.; Zhu, M.; Srinivasan, S.; Nwachukwu, J. C.; Cavett, V.; Min, J.; Carlson, K. E.; Wang, P.; Dong, C.; Katzenellenbogen, J. A.; Nettles, K. W.; Zhou, H. B. Development of selective estrogen receptor modulator (SERM)-like activity through an indirect mechanism of estrogen receptor antagonism: defining the binding mode of 7-oxabicyclo[2.2.1]hept-5-ene scaffold core ligands ChemMedChem 2012, 7, 1094-1100
    • (2012) ChemMedChem , vol.7 , pp. 1094-1100
    • Zheng, Y.1    Zhu, M.2    Srinivasan, S.3    Nwachukwu, J.C.4    Cavett, V.5    Min, J.6    Carlson, K.E.7    Wang, P.8    Dong, C.9    Katzenellenbogen, J.A.10    Nettles, K.W.11    Zhou, H.B.12


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.