Organic compounds -- part of the class 532-570 series – Organic compounds – Cyclopentanohydrophenanthrene ring system containing
Patent
1997-03-13
2000-04-18
Dees, Jose'G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Cyclopentanohydrophenanthrene ring system containing
C07J 100
Patent
active
060517263
ABSTRACT:
Disclosed is a method of preparing a compound represented by the following structural formula: ##STR1## The method comprises reacting bromine (Br.sub.2) and an aliphatic organic acid with a compound represented by the following structural formula: ##STR2## R.sub.1 and R.sub.2 are each independently a hydroxyl protecting group.
REFERENCES:
patent: 5405944 (1995-04-01), Suzuki et al.
Pert et al., "An alternative route to a 2-bromo- and 2-iodo-estradiols from estradiol"., Aust. J. Chem., vol. 40, pp. 303-309, 1987.
He et al., "A novel 1,3 O->C sillyl shift and deacylation reaction mediated by tetra-n-butylammonium flouride in an aromatic system". J. Org. Chem., vol. 60, pp. 5905-5909, 1995.
He et al., "A versatile synthesis of 2-methoxyestradio, an endogenous metaabolite of estradiol which inhibits tubulin polymerization by binding to the colchicine binding site". Bioorg. Med. Chem. Let., vol. 4(14), pp. 1725-1728, 1994.
Slaunwhite et al., "Bromination phenolic steroids. I. Substitution of estrone and 17.beta.-estradiol in ring A". J. Org. Chem., vol. 27, pp. 1749-1752, 1962.
Cushman, M., et al., "Synthesis of Analogs of 2-Methoxyestradiol with Enhanced Inhibitory Effects on Tubulin Polymerization and Cancer Cell Growth," J. Med. Chem. 40:2323-2334 (1997).
Numazawa, M., et al., "Synthesis of 2-Methoxy- and 4-Methoxy-Estrogens with Halogen-Methoxy Exchange Reaction," J. Chem. Res. Miniprint 11:3701-3715, Paper E/155/85 (Dec. 31, 1984).
Nambara, T., et al., "Studies on Steroid Conjugates. III. New Syntheses of 2-Methoxyestrogens," Chem. Pharm. Bull. 18(3):474-480 (1970).
Zheng, X-h, et al., "A New Synthetic Route to Pyrogallolestrogen Dimethyl Ethers by Nucleophilic Substitution of 2,4-Dibromoestrogens," Steroids 40(2):121-124 (1982).
Horiuchi, C.A., et al., "Novel Regioselective Iodination of Estradiol 17.beta.-Acetate," Bull. Chem. Soc. Jpn. 59(8):2459-2462 (1986).
D. J. Pert and D. D. Ridley, "Formylation of Oestrogens," Aust. J. Chem., 42:405-19 (1989).
D. J. Pert and D. D. Ridley, "An Alternative Route to 2-Bromo- and 2-Iodo-estradiols from Estradiol," Aust. J. Chem., 40:303-9 (1987.
S. Chen, et al., "A New Synthetic Route to 2- and 4-Methoxyestradiols by Nucleophilic Substitution," Steroids 47(1):63-66 (Jan. 1986).
P. N. Rao and J. E. Burdett, Jr., "Novel Two-Step Synthesis of 2-Methoxyestradiol," Synthesis, pp. 168-169 (Mar. 1977).
H. M. He, et al., "A Novel 1,3 O.fwdarw.C Silyl and Deacylation Reaction Mediated by Tetra-n-butylammonium Flouride in an Aromatic System," J. Org. Chem., 60:5905-5909 (1995).
W. R. Slaunwhite, Jr., and L. Neeley, Bromination of Phenolic Steroids. I. Substitution of Estrone and 17.beta.-Estradiol in Ring A.sup.1 Bromination of Phenolic Steroids I, J. Org. Chem. 27:1749-1752 (1962).
M. Cushman, et al., "Synthesis, Antitubulin and Antimitotic Activity, and Cytotoxicity of Analogs of 2-Methoxyestradiol, an Endogenous Mammalian Metabolite of Estradiol that Inhibits Tubulin Polymerization by Binding to the Colchicine Binding Site," J. Med. Chem. 38:2041-2049 (1995).
H. M. He and M. Cushman, "A Versatile Synthesis of 2-Methoxyestradiol, An Endogenous Metabolite of Estradiol which Inhibits Tubulin Polymerization by Binding to the Colchicine Binding Site," Bioroganic& Medicinal Chemistry Letters, 4(14):1725-1728 (1994).
Ram Siya
Sachdeva Yesh
Badio Barbara
Dees Jose'G.
Pharm-Eco Laboratories, Inc.
LandOfFree
Synthesis of 2-alkoxyestradiols does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Synthesis of 2-alkoxyestradiols, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of 2-alkoxyestradiols will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2337254