메뉴 건너뛰기




Volumn 36, Issue 9, 2013, Pages 1096-1103

Design, synthesis, and biological evaluation of cyclopropyl analogues of stilbene with raloxifene side chain as subtype-selective ligands for estrogen receptor

Author keywords

Binding affinity; Cyclopropane; Estrogen receptor; Gene transcription assay; Stilbene; Subtype selective ligand

Indexed keywords

2 (4 METHOXYPHENYL) 3 (4 PHENOXYLMETHYLPHENYL) PROPENAL; 2 [4 (BENZYLOXY)PHENYL] 1 (4 METHOXYPHENYL) CYCLOPROPANECARBALDEHYDE; 3 (4 BENZYLOXYPHENYL) 2 (4 METHOXYPHENYL) ACRYLONITRILE; 3 (4 BENZYLOXYPHENYL) 2 (4 METHOXYPHENYL)PROP 2 EN 1 OL; 4 [2 (4 METHOXYPHENYL) 2 METHYLCYCLOPROPYL]PHENOL; 4,4' (1 METHYLCYCLOPROPANE 1,2 DIYL)DIPHENOL; [1 2 BIS(4 HYDROXYPHENYL)CYCLOPROPYL][4 (2 (PIPERIDIN 1 YL)ETHOXY)PHENYL]METHANONE; [2 (4 (BENZYLOXY)PHENYL) 1 (4 METHOXYPHENYL) CYCLOPROPYL][4 (2 PIPERIDIN 1 YL)ETHOXY PHENYL]METHANONE; [2 (4 (BENZYLOXY)PHENYL) 1 (4 METHOXYPHENYL) CYCLOPROPYL][4 [2 (PIPERIDIN 1 YL)ETHOXY]PHENYL]METHANOL; [2 (4 HYDROXYPHENYL) 1 (4 METHOXYPHENYL) CYCLOPROPYL][4 (2 (PIPERIDIN 1 YL)ETHOXY)PHENYL]METHANONE; [2 4 (BENZYLOXYPHENYL) 1 (4 METHOXYPHENYL) CYCLOPROPYL] 2 METHANE; [2 4 (BENZYLOXYPHENYL) 1 (4 METHOXYPHENYL) CYCLOPROPYL]METHANOL; CYCLOPROPANE DERIVATIVE; DESS MARTIN PERIODINANE; DITHIOCARBONIC ACID O [2 (4 BENZYLOXYPHENYL) 1 (4 METHOXYPHENYL) CYCLOPROPYLMETHYL ] ESTER METHYL ESTER; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; RALOXIFENE; SELECTIVE ESTROGEN RECEPTOR MODULATOR; STILBENE DERIVATIVE; TAMOXIFEN; UNCLASSIFIED DRUG;

EID: 84884205885     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-013-0134-2     Document Type: Article
Times cited : (8)

References (16)
  • 1
    • 79551584513 scopus 로고    scopus 로고
    • Antiestrogens and their therapeutic applications in breast cancer and other diseases
    • 21054173 10.1146/annurev-med-052209-100305 1:CAS:528:DC%2BC3MXivVWhtL0%3D
    • Ali, S.; L. Buluwela, and R.C. Coombes. 2011. Antiestrogens and their therapeutic applications in breast cancer and other diseases. Annual Review of Medicine 62: 217-232.
    • (2011) Annual Review of Medicine , vol.62 , pp. 217-232
    • Ali, S.1    Buluwela, L.2    Coombes, R.C.3
  • 2
    • 0037029805 scopus 로고    scopus 로고
    • Synthesis of the racemic forms of carbon-carbon double bond locked analogues of strobilurins which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit
    • 10.1016/S0040-4020(02)00334-4 1:CAS:528:DC%2BD38XjtVeksrc%3D
    • Carpita, A.; A. Ribecai, R. Rossi, and P. Stabile. 2002. Synthesis of the racemic forms of carbon-carbon double bond locked analogues of strobilurins which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit. Tetrahedron 58: 3673-3680.
    • (2002) Tetrahedron , vol.58 , pp. 3673-3680
    • Carpita, A.1    Ribecai, A.2    Rossi, R.3    Stabile, P.4
  • 3
    • 0029028741 scopus 로고
    • Increasing the number of tandem estrogen response elements increases the estrogenic activity of a tamoxifen analogue
    • 7757959 10.1016/0304-3835(95)03755-L 1:CAS:528:DyaK2MXlvVSqsLc%3D
    • Catherino, W.H.; and V.C. Jordan. 1995. Increasing the number of tandem estrogen response elements increases the estrogenic activity of a tamoxifen analogue. Cancer Letters 92: 39-47.
    • (1995) Cancer Letters , vol.92 , pp. 39-47
    • Catherino, W.H.1    Jordan, V.C.2
  • 5
    • 84859509821 scopus 로고    scopus 로고
    • Changing concepts: Menopausal hormone therapy and breast cancer
    • 22427684 10.1093/jnci/djs014 1:CAS:528:DC%2BC38XlsFSitLY%3D
    • Chlebowski, R.T.; and G.L. Anderson. 2012. Changing concepts: Menopausal hormone therapy and breast cancer. Journal of the National Cancer Institute 104(7): 517-527.
    • (2012) Journal of the National Cancer Institute , vol.104 , Issue.7 , pp. 517-527
    • Chlebowski, R.T.1    Anderson, G.L.2
  • 6
    • 84860299273 scopus 로고    scopus 로고
    • Recent advances in the synthesis of raloxifene: A selective estrogen receptor modulator
    • 22405286 10.1016/j.ejmech.2012.02.021 1:CAS:528:DC%2BC38XmtlSls7c%3D
    • Dadiboyena, S. 2012. Recent advances in the synthesis of raloxifene: A selective estrogen receptor modulator. European Journal of Medicinal Chemistry 51: 17-34.
    • (2012) European Journal of Medicinal Chemistry , vol.51 , pp. 17-34
    • Dadiboyena, S.1
  • 7
    • 0025980442 scopus 로고
    • Synthesis and biological evaluation of a series of l,l-dichloro-2,2,3- triarylcyclopropanes as pure antiestrogens
    • 1995907 10.1021/jm00106a052 1:CAS:528:DyaK3MXhtVWgsrg%3D
    • Day, B.W.; R.A. Magarian, P.T. Jain, J.T. Pento, G.K. Mousissian, and K.L. Meyer. 1991. Synthesis and biological evaluation of a series of l,l-dichloro-2,2,3-triarylcyclopropanes as pure antiestrogens. Journal of Medicinal Chemistry 34: 842-851.
    • (1991) Journal of Medicinal Chemistry , vol.34 , pp. 842-851
    • Day, B.W.1    Magarian, R.A.2    Jain, P.T.3    Pento, J.T.4    Mousissian, G.K.5    Meyer, K.L.6
  • 8
    • 0001107133 scopus 로고
    • A novel route to cyclopropanes from olefins
    • 10.1016/S0040-4039(01)82791-X
    • Furukawa, J.; N. Kawabata, and J. Nishimura. 1966. A novel route to cyclopropanes from olefins. Tetrahedron Letters 28: 3353-3354.
    • (1966) Tetrahedron Letters , vol.28 , pp. 3353-3354
    • Furukawa, J.1    Kawabata, N.2    Nishimura, J.3
  • 9
    • 34249304805 scopus 로고    scopus 로고
    • Dihydro-[1H]-quinolin-2-ones as retinoid X receptor (RXR) agonists for potential treatment of dyslipidemia
    • 10.1016/j.bmcl.2007.01.049 1:CAS:528:DC%2BD2sXmtValsbs%3D
    • Lagu, B.; R. Lebedev, B. Pio, M. Yang, and P. Pelton. 2007. Dihydro-[1H]-quinolin-2-ones as retinoid X receptor (RXR) agonists for potential treatment of dyslipidemia. Bioorganic & Medicinal Chemistry Letters 17: 3491-3496.
    • (2007) Bioorganic & Medicinal Chemistry Letters , vol.17 , pp. 3491-3496
    • Lagu, B.1    Lebedev, R.2    Pio, B.3    Yang, M.4    Pelton, P.5
  • 11
    • 0031831058 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of cyclopropyl analogs of the antiestrogen MER 25
    • 10.1006/bioo.1998.1081 1:CAS:528:DyaK1cXkvV2jsbw%3D
    • Overacre, L.B.; and R.A. Magarian. 1998. Synthesis and biological evaluation of cyclopropyl analogs of the antiestrogen MER 25. Bioorganic Chemistry 26: 15-31.
    • (1998) Bioorganic Chemistry , vol.26 , pp. 15-31
    • Overacre, L.B.1    Magarian, R.A.2
  • 12
    • 0027322696 scopus 로고
    • Hormone- and DNA-binding mechanisms of the recombinant human estrogen receptor
    • 8512933 10.1021/bi00075a016 1:CAS:528:DyaK3sXktVWhs7w%3D
    • Obourn, J.D.; N.J. Koszewski, and A.C. Notides. 1993. Hormone- and DNA-binding mechanisms of the recombinant human estrogen receptor. Biochemistry 32: 6229-6236.
    • (1993) Biochemistry , vol.32 , pp. 6229-6236
    • Obourn, J.D.1    Koszewski, N.J.2    Notides, A.C.3
  • 13
    • 77956652851 scopus 로고    scopus 로고
    • SERMs: Progress and future perspectives
    • 20580502 10.1016/j.maturitas.2010.05.009 1:CAS:528:DC%2BC3cXhtFOntLrF
    • Pickar, J.H.; T. MacNeil, and K. Ohleth. 2010. SERMs: Progress and future perspectives. Maturitas 67: 129-138.
    • (2010) Maturitas , vol.67 , pp. 129-138
    • Pickar, J.H.1    Macneil, T.2    Ohleth, K.3
  • 14
    • 0033198735 scopus 로고    scopus 로고
    • Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist
    • 10469641 10.1093/emboj/18.17.4608 1:CAS:528:DyaK1MXmt1yisLo%3D
    • Pike, A.C.; A.M. Brzozowski, R.E. Hubbard, T. Bonn, A.G. Thorsell, O. Engstrom, J. Ljunggren, J.A. Gustafsson, and M. Carlquist. 1999. Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist. EMBO Journal 18: 4608-4618.
    • (1999) EMBO Journal , vol.18 , pp. 4608-4618
    • Pike, A.C.1    Brzozowski, A.M.2    Hubbard, R.E.3    Bonn, T.4    Thorsell, A.G.5    Engstrom, O.6    Ljunggren, J.7    Gustafsson, J.A.8    Carlquist, M.9
  • 15
    • 0345628994 scopus 로고
    • Cyclopropane derivatives. II. The electric moments of some alicyclic compounds
    • 21024889 10.1021/ja01209a039 1:CAS:528:DyaH28XitVakug%3D%3D
    • Rogers, M.T.; and J.D. Roberts. 1946. Cyclopropane derivatives. II. The electric moments of some alicyclic compounds. Journal of the American Chemical Society 68: 843-846.
    • (1946) Journal of the American Chemical Society , vol.68 , pp. 843-846
    • Rogers, M.T.1    Roberts, J.D.2
  • 16
    • 18744383698 scopus 로고    scopus 로고
    • Non-steroidal subtype selective estrogens
    • 15892637 10.2174/0929867053764662 1:CAS:528:DC%2BD2MXktlantLw%3D
    • Veeneman, G.H. 2005. Non-steroidal subtype selective estrogens. Current Medicinal Chemistry 12: 1077-1136.
    • (2005) Current Medicinal Chemistry , vol.12 , pp. 1077-1136
    • Veeneman, G.H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.