메뉴 건너뛰기




Volumn 77, Issue 5, 2012, Pages 467-470

A simple and convenient synthesis of 2-methoxyestradiol from estrone

Author keywords

2 Methoxyestradiol; Breast cancer; Total synthesis

Indexed keywords

2 METHOXYESTRADIOL; ESTRONE;

EID: 84858342180     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2012.01.005     Document Type: Article
Times cited : (7)

References (26)
  • 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
    • J.A. Katzenellenbogen, and J.A. Katzenellenbogen The 2010 Philip S. Portoghese Medicinal Chemistry Lectureship: addressing the "core issue" in the design of estrogen receptor ligands J Med Chem 54 2011 5271 5282
    • (2011) J Med Chem , vol.54 , pp. 5271-5282
    • Katzenellenbogen, J.A.1    Katzenellenbogen, J.A.2
  • 3
    • 0037397635 scopus 로고    scopus 로고
    • Estrogen and cognitive functioning in women
    • DOI 10.1210/er.2001-0016
    • B.B. Sherwin Estrogen and cognitive functioning in women Endocr Rev 24 2003 133 151 (Pubitemid 36515282)
    • (2003) Endocrine Reviews , vol.24 , Issue.2 , pp. 133-151
    • Sherwin, B.B.1    McGill, J.2
  • 4
    • 0030748869 scopus 로고    scopus 로고
    • Development of estrogen antagonists as pharmaceutical agents
    • S. Ray, and I. Dwivedy Development of estrogen antagonists as pharmaceutical agents Adv Drug Res 29 1997 171 270 (Pubitemid 27368069)
    • (1997) Advances in Drug Research , vol.29 , pp. 171-270
    • Ray, S.1    Dwivedy, I.2
  • 5
    • 0037435046 scopus 로고    scopus 로고
    • Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 1. Receptor interactions
    • DOI 10.1021/jm020449y
    • V.C. Jordan Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 1. Receptor interactions J Med Chem 46 2003 883 908 (Pubitemid 36423135)
    • (2003) Journal of Medicinal Chemistry , vol.46 , Issue.6 , pp. 883-908
    • Jordan, V.C.1
  • 6
    • 79953005259 scopus 로고    scopus 로고
    • Injectable delivery system of 2-methoxyestradiol for breast cancer therapy using biodegradable thermosensitive poly(organophosphazene) hydrogel
    • J.K. Cho, K.Y. Hong, J.W. Park, H.K. Yang, and S.C. Song Injectable delivery system of 2-methoxyestradiol for breast cancer therapy using biodegradable thermosensitive poly(organophosphazene) hydrogel J Drug Target 19 2011 270 280
    • (2011) J Drug Target , vol.19 , pp. 270-280
    • Cho, J.K.1    Hong, K.Y.2    Park, J.W.3    Yang, H.K.4    Song, S.C.5
  • 7
    • 57649097524 scopus 로고    scopus 로고
    • 2-Methoxyestradiol mediates apoptosis through caspase-dependent and independent mechanisms in ovarian cancer cells but not in normal counterparts
    • S. Kato, A. Sadarangani, S. Lange, M. Ana, A.M. Delpiano, M. Vargas, J. Brañes, J. Carvajal, G.I. Owen, and G.I. Owen 2-Methoxyestradiol mediates apoptosis through caspase-dependent and independent mechanisms in ovarian cancer cells but not in normal counterparts Reprod Sci 15 2008 878 894
    • (2008) Reprod Sci , vol.15 , pp. 878-894
    • Kato, S.1    Sadarangani, A.2    Lange, S.3    Ana, M.4    Delpiano, A.M.5    Vargas, M.6    Brañes, J.7    Carvajal, J.8    Owen, G.I.9    Owen, G.I.10
  • 8
    • 0037320432 scopus 로고    scopus 로고
    • 2-methoxyestradiol, a promising anticancer agent
    • DOI 10.1592/phco.23.2.165.32088
    • J. Nehal, N.J. Lakhani, M.A. Sarkar, J. Venitz, and W.D. Figg 2-Methoxyestradiol, a promising anticancer agent: metabolism of estrogens Pharmacotherapy 23 2003 165 172 (Pubitemid 36197457)
    • (2003) Pharmacotherapy , vol.23 , Issue.2 , pp. 165-172
    • Lakhani, N.J.1    Sarkar, M.A.2    Venitz, J.3    Figg, W.D.4
  • 10
    • 0030069601 scopus 로고    scopus 로고
    • Interactions of 2-methoxyestradiol, an endogenous mammalian metabolite, with unpolymerized tubulin and with tubulin polymers
    • DOI 10.1021/bi951559s
    • E. Hamel, C.M. Lin, E. Flynn, and R.J. D'Amato Interactions of 2-methoxyestradiol, an endogenous mammalian metabolite, with unpolymerized tubulin and with tubulin polymer Biochemistry 35 1996 1304 1310 (Pubitemid 26050794)
    • (1996) Biochemistry , vol.35 , Issue.4 , pp. 1304-1310
    • Hamel, E.1    Lin, C.M.2    Flynn, E.3    D'Amato, R.J.4
  • 11
    • 0028220858 scopus 로고
    • The endogenous oestrogen metabolite 2-methoxyoestradiol inhibits angiogenesis and suppresses tumour growth
    • DOI 10.1038/368237a0
    • T. Fotsis, Y. Zhang, M.S. Pepper, H. Adlercreutz, R. Montesano, P.P. Nawroth, and L. Schweigerer The endogenous oestrogen metabolite 2-methoxyestradiol inhibits angiogenesis and suppresses tumour growth Nature 368 1994 237 239 (Pubitemid 24108838)
    • (1994) Nature , vol.368 , Issue.6468 , pp. 237-239
    • Fotsis, T.1    Zhang, Y.2    Pepper, M.S.3    Adlercreutz, H.4    Montesano, R.5    Nawrotht, P.P.6    Schweigerer, L.7
  • 13
    • 58849135484 scopus 로고    scopus 로고
    • Mechanism of 2-methoxyestradiol induced apoptosis and growth arrest in human breast cancer cells
    • M. Fukai, J. Song, and B.T. Zhu Mechanism of 2-methoxyestradiol induced apoptosis and growth arrest in human breast cancer cells Mol Carcinogen 48 2009 66 78
    • (2009) Mol Carcinogen , vol.48 , pp. 66-78
    • Fukai, M.1    Song, J.2    Zhu, B.T.3
  • 14
    • 79954421458 scopus 로고    scopus 로고
    • Hatch S.2-Methoxyestradion, an endogenous estrogen metabolite, sensitizes radioresistance MCF-7/FIR breast cancer cells through multiple mechanism
    • S. Salama, C. Diaz-Arrastia, D. Patel, and S. Botting Hatch S.2-Methoxyestradion, an endogenous estrogen metabolite, sensitizes radioresistance MCF-7/FIR breast cancer cells through multiple mechanism Int J Radiat Oncol Biol Phys 80 2011 e231 239
    • (2011) Int J Radiat Oncol Biol Phys , vol.80 , pp. 231-239
    • Salama, S.1    Diaz-Arrastia, C.2    Patel, D.3    Botting, S.4
  • 15
    • 79955989699 scopus 로고    scopus 로고
    • 2-Methoxyestradiol analogue ENMD-1198 reduces breast cancer-induced osteolysis and tumour burden both in vitro and in vivo
    • J.A. Thomas, I.M. Mol, I. Que, E.L. Kaijzel, and C.W.G.M. Lowik 2-Methoxyestradiol analogue ENMD-1198 reduces breast cancer-induced osteolysis and tumour burden both in vitro and in vivo Mol Can Ther 10 2011 874 882
    • (2011) Mol Can Ther , vol.10 , pp. 874-882
    • Thomas, J.A.1    Mol, I.M.2    Que, I.3    Kaijzel, E.L.4    Lowik, C.W.G.M.5
  • 17
    • 0037764867 scopus 로고    scopus 로고
    • Short synthesis of 2-methoxyestradiol and 2-hydroxyestradiol
    • DOI 10.1016/S0039-128X(03)00035-7
    • P.S. Kiuru, and K. Wahala Short synthesis of 2-methoxyestradiol and 2-hydroxyestradiol Steroids 68 2003 373 375 (Pubitemid 36638249)
    • (2003) Steroids , vol.68 , Issue.4 , pp. 373-375
    • Kiuru, P.S.1    Wahala, K.2
  • 18
    • 0036890192 scopus 로고    scopus 로고
    • A new practical synthesis of 2-methoxyestradiol
    • P.N. Rao, and J.W. Cessac A new practical synthesis of 2-methoxyestradiol Steroids 67 2002 1065 1070
    • (2002) Steroids , vol.67 , pp. 1065-1070
    • Rao, P.N.1    Cessac, J.W.2
  • 19
    • 0022973788 scopus 로고
    • A new synthetic route to 2- and 4-methoxyestradiols by nucleophilic substitution
    • S.H. Chen, G.R. Luo, X.S. Wu, M. Chen, and H.M. Zhao A new synthetic route to 2- and 4-methoxyestradiols by nucleophilic substitution Steroids 47 1986 63 66
    • (1986) Steroids , vol.47 , pp. 63-66
    • Chen, S.H.1    Luo, G.R.2    Wu, X.S.3    Chen, M.4    Zhao, H.M.5
  • 20
    • 71749121930 scopus 로고
    • Effects of components of crown-CuI mixed catalyst on nucleophilic substitution of bromoestrogen
    • G.R. Luo, S.H. Chen, and H.M. Zhang Effects of components of crown-CuI mixed catalyst on nucleophilic substitution of bromoestrogen Chin J Org Chem 9 1989 266 268
    • (1989) Chin J Org Chem , vol.9 , pp. 266-268
    • Luo, G.R.1    Chen, S.H.2    Zhang, H.M.3
  • 21
    • 0031793090 scopus 로고    scopus 로고
    • An optimized synthesis of 2-methoxyestradiol, a naturally occurring human metabolite with anticancer activity
    • Z. Wang, and M. Cushman An optimized synthesis of 2-methoxyestradiol, a naturally occurring human metabolite with anticancer activity Synth Commun 28 1998 4431 4437 (Pubitemid 28487984)
    • (1998) Synthetic Communications , vol.28 , Issue.23 , pp. 4431-4437
    • Wang, Z.1    Cushman, M.2
  • 22
    • 71849086800 scopus 로고    scopus 로고
    • An efficient practical synthesis of 2-methoxyestradiol
    • M. Xin, Q. You, and H. Xiang An efficient practical synthesis of 2-methoxyestradiol Steroids 75 2010 53 56
    • (2010) Steroids , vol.75 , pp. 53-56
    • Xin, M.1    You, Q.2    Xiang, H.3
  • 23
    • 80052406888 scopus 로고    scopus 로고
    • Ortho-formylation of estrogens. Synthesis of the anti-cancer agent 2-methoxyestradiol
    • O.W. Akselsen, and T.V. Hansen Ortho-formylation of estrogens. Synthesis of the anti-cancer agent 2-methoxyestradiol Tetrahedron 67 2011 7738 7742
    • (2011) Tetrahedron , vol.67 , pp. 7738-7742
    • Akselsen, O.W.1    Hansen, T.V.2
  • 24
    • 84942705127 scopus 로고
    • Joint Commission on Biochemical Nomenclature (JCBN). Nomenclature of steroids
    • IUPAC
    • IUPAC Joint Commission on Biochemical Nomenclature (JCBN). Nomenclature of steroids Pure Appl Chem 61 1989 1783 1822
    • (1989) Pure Appl Chem , vol.61 , pp. 1783-1822
  • 26
    • 13944262441 scopus 로고    scopus 로고
    • A simple regioselective demethylation of p-aryl methyl ethers using aluminum chloride-dichloromethane system
    • DOI 10.1081/SCC-200046477
    • A.S. Negi, S.K. Chattopadhyay, S. Srivastava, and A.K. Bhattacharya A simple regioselective demethylation of p-aryl methyl ethers using aluminium chloride-dichloromethane system Synth Commun 35 2005 15 21 (Pubitemid 40270830)
    • (2005) Synthetic Communications , vol.35 , Issue.1 , pp. 15-21
    • Negi, A.S.1    Chattopadhyay, S.K.2    Srivastava, S.3    Bhattacharya, A.K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.