Synthesis of 7α-substituted derivatives of 17β-estradiol
Tài liệu tham khảo
Parkin, 2001, Estimating the world cancer burden: Globocan, Int J Cancer, 94, 153, 10.1002/ijc.1440
Jordan, 1995, Third annual William L. McGuire Memorial Lecture. Studies on the estrogen receptor in breast cancer—20 years as a target for the treatment and prevention of cancer, Breast Cancer Res Treat, 36, 267, 10.1007/BF00713399
MacGregor, 1998, Basic guide to the mechanisms of antiestrogen action, Pharmacol Rev, 50, 151
Osborne, 2004, Fulvestrant: an estrogen receptor antagonist with a novel mechanism of action, Br J Cancer, 90, S2, 10.1038/sj.bjc.6601629
Bowler, 1989, Novel steroidal pure antiestrogens, Steroids, 54, 71, 10.1016/0039-128X(89)90076-7
Jones, 2003, Fulvestrant: an estrogen receptor antagonist that downregulates the estrogen receptor, Semin Oncol, 30, 14, 10.1053/j.seminoncol.2003.08.003
Adamczyk, 1997, A stereoselective synthesis of 7α-(3-carboxypropyl) estradiol from a noncontrolled substance, Steroids, 62, 771, 10.1016/S0039-128X(97)00088-3
Hussey, 2002, Synthesis of chimeric 7α-substituted estradiol derivatives linked to cholesterol and cholesterylamine, Org Lett, 4, 415, 10.1021/ol0171261
Skaddan, 1999, Synthesis and binding affinities of novel re-containing 7α-substituted estradiol complexes: models for breast cancer imaging agents, J Org Chem, 64, 8108, 10.1021/jo990641g
Seimbille, 2002, Synthesis of 16α-fluoro ICI, 182,780 derivatives: powerful antiestrogens to image estrogen receptor densities in breast cancer by positron emission tomography, J Chem Soc, Perkin Trans, 1, 2275, 10.1039/B205571F
Mitra, 2002, A rationally designed genotoxin that selectively destroys estrogen receptor-positive breast cancer cells, J Am Chem Soc, 124, 1862, 10.1021/ja017344p
Hussey, 2003, Synthesis of a β-estradiol-biotin chimera that potently heterodimerizes estrogen receptor and strepavidin proteins in a yeast three-hybrid system, J Am Chem Soc, 125, 3692, 10.1021/ja0293305
Lee, 2001, Characterization of the NADPH-dependent metabolism of 17β-estradiol to multiple metabolites by human liver microsomes and selectively expressed human cytochrome P450 3A4 and 3A5, J Pharmacol Exp Ther, 298, 420
Lovely, 1996, 2-(Hydroxyalkyl)estradiols: synthesis and biological evaluation, J Med Chem, 39, 1917, 10.1021/jm9508245
Liu, 2004, Concentration-dependent mitogenic and antiproliferative actions of 2-methoxyestradiol in estrogen receptor-positive human breast cancer cells, J Steroid Biochem Mol Biol, 88, 265, 10.1016/j.jsbmb.2003.12.003
Pearson, 1985, Benzylic oxidation using tert-butyl hydroperoxide in the presence of chromium hexacarbonyl, J Org Chem, 50, 2791, 10.1021/jo00215a043
Rather, 1986, A convenient method of benzylic oxidation with pyridinium chlorochromate, Synth Commun, 16, 1493, 10.1080/00397918608056400
Takagishi, 1991, Fluorine- and trifluoromethyl-substituted toluenes: site selective metalation of aromatic or benzylic positions, Synlett, 119, 10.1055/s-1991-20650
Tedesco, 1995, 6-Oxoestradiols from estradiols: exploiting site selective metalation of aralkyl systems with superbases, Synthesis, 1493, 10.1055/s-1995-4136
Akanni, 1984, Improved preparation of 3β,17β-diacetoxyoestra-1,3,5(10)-trien-6-one, Synth Commun, 14, 713
Takagi, 1991, Synthesis and mechanism of hydrolysis of estrogen 6-sulfates: model compounds for demonstrating the carcinogenesis of estrogen, Steroids, 56, 173, 10.1016/0039-128X(91)90078-A
Parish, 1986, Pyridinium chlorochromate-mediated allylic and benzylic oxidation, Synth Commun, 16, 1371, 10.1080/00397918608056385
Mancuso, 1978, Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide “activated” by oxalyl chloride, J Org Chem, 43, 2480, 10.1021/jo00406a041
Bucourt, 1978, New biospecific adsorbents for the purification of estradiol receptor, J Biol Chem, 253, 8821, 10.1016/S0021-9258(17)34385-5
Bessodes, 1996, A new highly efficient procedure for the monobenzylation of symmetrical diols, Synlett, 1119, 10.1055/s-1996-5663
Tedesco, 1997, An expeditious route to 7α-substituted estradiol derivatives, Tetrahedron Lett, 38, 7997, 10.1016/S0040-4039(97)10180-0
Srikrishana, 1995, A simple and convenient one-step method for the reductive deoxygenation of aryl ketones to hydrocarbons, Synlett, 93, 10.1055/s-1995-4866
Burnham, 1971, Hydrogenolysis of carbonyl derivatives as a route to pure aliphatic–aromatic hydrocarbons, J Org Chem, 36, 737, 10.1021/jo00804a032
Bowler, 1989, Novel steroidal pure antiestrogens, Steroids, 54, 71, 10.1016/0039-128X(89)90076-7
Huang M. Reducing steroid ketones to their corresponding methylene analogs. US Patent 2,648,686. Merck & Co. Inc.; 11 August 1953.
Huang, 1949, Reduction of steroid ketones and other carbonyl compounds by modified Wolff–Kishner method, J Am Chem Soc, 71, 3301, 10.1021/ja01178a008