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Volumn 70, Issue 3, 2005, Pages 173-178

Synthesis of the catechols of natural and synthetic estrogens by using 2-iodoxybenzoic acid (IBX) as the oxidizing agent

Author keywords

2 Iodoxybenzoic acid (IBX); Catechol synthesis; Dienestrol; Diethylstilbestrol; Estradiol; Estrone; Hexestrol

Indexed keywords

2 HYDROXYESTRADIOL; 2 HYDROXYESTRONE; 2 IODYLBENZOIC ACID; 3' HYDROXYDIENESTROL; 3' HYDROXYDIETHYLSTILBESTROL; 3' HYDROXYHEXESTROL; 4 HYDROXYESTRADIOL; 4 HYDROXYESTRONE; ASCORBIC ACID; BENZOIC ACID DERIVATIVE; BORON TRIBROMIDE; CATECHOL ESTROGEN; DICHLOROMETHANE; DIENESTROL; DIETHYLSTILBESTROL; ESTRADIOL; ESTRONE; ESTRONE DERIVATIVE; N,N DIMETHYLFORMAMIDE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 14844307099     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2004.11.005     Document Type: Article
Times cited : (41)

References (28)
  • 1
    • 0023836871 scopus 로고
    • Estrogens as a cause of human cancer: The Richard and Hinda Rosenthal Foundation Award Lecture
    • B.E. Henderson, R. Ross, and L. Bernstein Estrogens as a cause of human cancer: the Richard and Hinda Rosenthal Foundation Award Lecture Cancer Res 48 1988 246 253
    • (1988) Cancer Res , vol.48 , pp. 246-253
    • Henderson, B.E.1    Ross, R.2    Bernstein, L.3
  • 3
    • 0026331038 scopus 로고
    • Toward the primary prevention of cancer
    • B.E. Henderson, R.K. Ross, and M.C. Pike Toward the primary prevention of cancer Science 254 1991 1131 1138
    • (1991) Science , vol.254 , pp. 1131-1138
    • Henderson, B.E.1    Ross, R.K.2    Pike, M.C.3
  • 4
    • 0021021999 scopus 로고
    • Relative carcinogenic activity of various synthetic and natural estrogens in the Syrian hamster kidney
    • J.J. Li, S.A. Li, J.K. Klicka, J.A. Parsons, and L.K. Lam Relative carcinogenic activity of various synthetic and natural estrogens in the Syrian hamster kidney Cancer Res 43 1983 5200 5204
    • (1983) Cancer Res , vol.43 , pp. 5200-5204
    • Li, J.J.1    Li, S.A.2    Klicka, J.K.3    Parsons, J.A.4    Lam, L.K.5
  • 6
    • 0023181602 scopus 로고
    • Estrogen carcinogenesis in Syrian hamster tissue: Role of metabolism
    • J.J. Li, and S.A. Li Estrogen carcinogenesis in Syrian hamster tissue: role of metabolism Fed Proc 46 1987 1858 1863
    • (1987) Fed Proc , vol.46 , pp. 1858-1863
    • Li, J.J.1    Li, S.A.2
  • 7
    • 0034650264 scopus 로고    scopus 로고
    • Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens
    • R.R. Newbold, and J.G. Liehr Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens Cancer Res 60 2000 235 237
    • (2000) Cancer Res , vol.60 , pp. 235-237
    • Newbold, R.R.1    Liehr, J.G.2
  • 10
    • 0037123341 scopus 로고    scopus 로고
    • Endogenous sex hormones and breast cancer in postmenopausal women: Reanalysis of nine prospective studies
    • The Endogenous Hormones and Breast Cancer Collaborative Group. Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies. J Natl Cancer Inst 2002;94:606-16.
    • (2002) J Natl Cancer Inst , vol.94 , pp. 606-616
  • 11
    • 0034463957 scopus 로고    scopus 로고
    • Is estradiol a genotoxic mutagenic carcinogen?
    • J.G. Liehr Is estradiol a genotoxic mutagenic carcinogen? Endocr Rev 21 2000 40 54
    • (2000) Endocr Rev , vol.21 , pp. 40-54
    • Liehr, J.G.1
  • 13
    • 1242274631 scopus 로고    scopus 로고
    • The role of endogenous catechol quinones in the initiation of cancer and neurodegenerative diseases
    • H. Sies L. Packer Elsevier Duesseldorf, Germany
    • E. Cavalieri, E. Rogan, and D. Chakaravarti The role of endogenous catechol quinones in the initiation of cancer and neurodegenerative diseases H. Sies L. Packer Methods in enzymology, quinones and quinone enzymes. Part B 2004 Elsevier Duesseldorf, Germany 293 319
    • (2004) Methods in Enzymology, Quinones and Quinone Enzymes. Part B , pp. 293-319
    • Cavalieri, E.1    Rogan, E.2    Chakaravarti, D.3
  • 14
    • 0018853550 scopus 로고
    • Catechol estrogens (2- and 4-hydroxyestrogens): Chemistry, biogenesis, metabolism, occurrence and physiological significance
    • P. Ball, and R. Knuppen Catechol estrogens (2- and 4-hydroxyestrogens): chemistry, biogenesis, metabolism, occurrence and physiological significance Acta Endocrinol 93 Suppl. 232 1980 1 127
    • (1980) Acta Endocrinol , vol.93 , Issue.232 SUPPL. , pp. 1-127
    • Ball, P.1    Knuppen, R.2
  • 15
    • 0031848636 scopus 로고    scopus 로고
    • Functional role of estrogen metabolism in target cells: Review and perspectives
    • B.T. Zhu, and A.H. Conney Functional role of estrogen metabolism in target cells: review and perspectives Carcinogenesis 19 1998 1 27
    • (1998) Carcinogenesis , vol.19 , pp. 1-27
    • Zhu, B.T.1    Conney, A.H.2
  • 16
    • 0019738999 scopus 로고
    • Oxidative metabolism of the synthetic estrogens hexestrol and dienestrol indicates reactive intermediate
    • M. Metzler, and J.A. McLachlan Oxidative metabolism of the synthetic estrogens hexestrol and dienestrol indicates reactive intermediate Adv Exp Med Biol 136A 1981 829 837
    • (1981) Adv Exp Med Biol , vol.136 , pp. 829-837
    • Metzler, M.1    McLachlan, J.A.2
  • 17
    • 0022394675 scopus 로고
    • In vitro metabolism of diethylstilbestrol by hepatic, renal and uterine microsomes of rats and hamsters
    • H. Haaf, and M. Metzler In vitro metabolism of diethylstilbestrol by hepatic, renal and uterine microsomes of rats and hamsters Biochem Pharmacol 34 1985 3107 3115
    • (1985) Biochem Pharmacol , vol.34 , pp. 3107-3115
    • Haaf, H.1    Metzler, M.2
  • 19
    • 0025189604 scopus 로고
    • Effects of various inducers on diethylstilbestrol metabolism, drug-metabolizing enzyme activities and the aromatic hydrocarbon (Ah) receptor in male Syrian hamster liver
    • G. Blaich, M. Gattlicher, P. Cikryt, and M. Metzler Effects of various inducers on diethylstilbestrol metabolism, drug-metabolizing enzyme activities and the aromatic hydrocarbon (Ah) receptor in male Syrian hamster liver J Steroid Biochem 35 1990 201 204
    • (1990) J Steroid Biochem , vol.35 , pp. 201-204
    • Blaich, G.1    Gattlicher, M.2    Cikryt, P.3    Metzler, M.4
  • 20
    • 2742581682 scopus 로고
    • Catechol derivatives of estrogens
    • J. Fishman, M. Tomasz, and R. Lehman Catechol derivatives of estrogens J Org Chem 25 1960 585 588
    • (1960) J Org Chem , vol.25 , pp. 585-588
    • Fishman, J.1    Tomasz, M.2    Lehman, R.3
  • 21
    • 0013160131 scopus 로고
    • Synthesis of 2-hydroxyestradiol-17β
    • P.N. Rao, and L.R. Axelrod Synthesis of 2-hydroxyestradiol-17β Tetrahedron 10 1960 144 147
    • (1960) Tetrahedron , vol.10 , pp. 144-147
    • Rao, P.N.1    Axelrod, L.R.2
  • 22
    • 84943861606 scopus 로고
    • Simple preparation of catechol estrogen and its derivatives
    • I. Yoshizawa, M. Tamura, and M. Kimura Simple preparation of catechol estrogen and its derivatives Chem Pharm Bull 20 1972 1842 1843
    • (1972) Chem Pharm Bull , vol.20 , pp. 1842-1843
    • Yoshizawa, I.1    Tamura, M.2    Kimura, M.3
  • 23
    • 0017093511 scopus 로고
    • Convenient large scale preparation of catechol estrogens
    • G. Stubenrauch, and R. Knuppen Convenient large scale preparation of catechol estrogens Steroids 28 1976 733 741
    • (1976) Steroids , vol.28 , pp. 733-741
    • Stubenrauch, G.1    Knuppen, R.2
  • 24
    • 0015577667 scopus 로고
    • A simple chemical method for the synthesis of catechol estrogens
    • H.P. Gelbke, O. Haupt, and R. Knuppen A simple chemical method for the synthesis of catechol estrogens Steroids 21 1973 205 218
    • (1973) Steroids , vol.21 , pp. 205-218
    • Gelbke, H.P.1    Haupt, O.2    Knuppen, R.3
  • 25
    • 0031801771 scopus 로고    scopus 로고
    • Large-scale synthesis of the catechol metabolites of diethylstilbestrol and hexestrol
    • S-T. Jan, E.G. Rogan, and E.L. Cavalieri Large-scale synthesis of the catechol metabolites of diethylstilbestrol and hexestrol Chem Res Toxicol 11 1998 408 411
    • (1998) Chem Res Toxicol , vol.11 , pp. 408-411
    • Jan, S.-T.1    Rogan, E.G.2    Cavalieri, E.L.3
  • 26
    • 0033546262 scopus 로고    scopus 로고
    • A user friendly entry to 2-iodoxybenzoic acid (IBX)
    • M. Frigerio, M. Santagostino, and S. Sputore A user friendly entry to 2-iodoxybenzoic acid (IBX) J Org Chem 64 1999 4537 4538
    • (1999) J Org Chem , vol.64 , pp. 4537-4538
    • Frigerio, M.1    Santagostino, M.2    Sputore, S.3
  • 27
    • 0037165401 scopus 로고    scopus 로고
    • Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX)
    • D. Magdziak, A.A. Rodriguez, R.W. VanDeWater, and T.R.R. Pettus Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX) Org Lett 4 2002 285 288
    • (2002) Org Lett , vol.4 , pp. 285-288
    • Magdziak, D.1    Rodriguez, A.A.2    Vandewater, R.W.3    Pettus, T.R.R.4
  • 28
    • 0015517602 scopus 로고
    • A new method for preventing oxidative decomposition of catechol estrogens during chromatography
    • H.P. Gelbke, and R. Knuppen A new method for preventing oxidative decomposition of catechol estrogens during chromatography J Chromatogr 71 1972 465 471
    • (1972) J Chromatogr , vol.71 , pp. 465-471
    • Gelbke, H.P.1    Knuppen, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.