Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Patent
1993-03-12
1995-05-02
Richter, Johann
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
558 17, C07C33104
Patent
active
054119863
ABSTRACT:
Sulforaphane has been isolated and identified as a major and very potent phase II enzyme inducer in broccoli (Brassica oleracea italica). Sulforaphane is a monofunctional inducer, inducing phase II enzymes selectively without the induction of aryl hydrocarbon receptor-dependent cytochromes P-450 (phase I enzymes). Analogues differing in the oxidation state of sulfur and the number of methylene groups were synthesized, and their inducer potencies were measured. Sulforaphane is the most potent of these analogues. Other analogues having different substituent groups in place of the methylsulfinyl group of sulforaphane were also synthesized and assessed. Of these, the most potent are 6-isothiocyanato-2-hexanone and exo-2-acetyl-6-isothiocyanatonorbornane.
REFERENCES:
Kjaer, et al., "isoThiocyanates XXX. Glucohirsutin, a New Naturally Occurring Glucoside Furnishing (-)-8-Methylsulphinyl-octyl isoThiocyanate on Enzymic Hydrolysis", Acta Chem. Scand. 12(5):833-838 (1958).
McKay, et al., "Bacteriostats. II. The Chemical and Bacteriostatic Properties of Isothiocyanates and their Derivatives," J. Amer. Chem. Soc. 81(16):4328-4335 (1959).
Kjaer, "Naturally Derived isoThiocyanates (Mustard Oils) and Their Parent Glucosides," Progress in the Chemistry of Organic Natural Products, 18:138-176 (1960).
Mislow, et al., "Diastereoisomerism in 9-Dimethylamino-9,10-dihydro-4,5-dimethylphenanthrene" J. Amer. Chem. Soc., 87(3):665-666 (1965).
Balenovi, et al., "Synthesis of (.+-.) Sulphoraphene", Tetrahedron, 22:2139-2143 (1966).
Hansen, et al., "Intramolecular Cyclizations of Thioureas Derived From Sulphoraphene: a Case of Asymmetrically Induced Additions to Vinylic Sulphoxides", Acta Chemica Scandinavica B 28:418-424 (1974).
Lam, et al., "Isolation and Identification of Kahweol Palmitate and Cafestol Palmitate as Active Constituents of Green Coffee Beans That Enhance Glutathione S-Transferase Activity in the Mouse", Cancer Research, 42:1193-1198 (1982).
Wattenberg, et al., "Inhibitory Effects of 5-(2-pyraziny)-4-methyl-1,2-dithiol-3-thione(Oltipraz) on Carcinogenesis Induced by Benzo[a]pyrene, Diethylnitrosamine and Uracil Mustard," Carcinogenesis, 7(8):1379-1381 (1986).
Prochaska, et al., "Direct Measurement of NAD(P)H:Quinone Reductase from Cells Cultured in Microtiter Wells: A Screening Assay for Anticarcinogenic Enzyme Inducers", Analytical Biochemistry, 169:328-336 (1988).
Prochaska, et al., "Regulatory Mechanisms of Monofunctional and Bifunctional Anticarcinogenic Enzyme Inducers in Murine Liver", Cancer Research, 48:4776-4782 (1988).
Wattenberg, et al., "Chemoprevention of Cancer", Cancer Research, 45:1-8 (1985).
Prochaska, "Rapid Detection of Inducers of Enzymes That Protect Against Carcinogens", Proc. Natl. Acad. Sci. USA, 89:2394-2398 (1992).
Wattenberg, et al., "Inhibitory Effects of Benzyl Isothiocyanate Administered Shortly Before Diethlnitrosamine or Benzo[a]pyrene on Pulmonary and Forestomach Neoplasia in A/J Mice," Carcinogenesis, 8(12):1971-1973, 1987.
Morse, et al., "Effects of Alkyl Chain Length on the Inhibition of NNK-Induced Lung Neoplasia in A/J Mice by Arylalkyl Isothiocyanates", Carcinogenesis, 10(9):1757-1759, 1989.
Stoner, et al., "Inhibitory Effects of Phenethyl Isothiocyanate on N-Nitrosobenzylmethylamine Carcinogenesis in the Rat Esophagus," Cancer Research 51:2063-2068, 1991.
Doerr-O'Rourke, et al., "Effect of Phenethyl Isothiocyanate on the Metabolism of the Tobacco-Specific Nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by Cultured Rat Lung Tissue," Carcinogenesis, 12(6):1029-1034, 1991.
Wattenberg, et al., "Inhibition of Carcinogenic Effects of Polycyclic Hydrocarbons by Benzyl Isothiocyanate and Related Compounds," J. Natl Cancer, 48(2):395-398, 1977.
Sparnins, et al., "Enhancement of Glutathione S-Transferase Activity of the Mouse Forestomach by Inhibitors of Benzo[a]pyrene-Induced Neoplasia of the Forestomach", Jncl., 66(4):769-771, 1981.
Cho Cheon-Gyu
Posner Gary H.
Talalay Paul
Zhang Yuesheng
McKane Joseph K.
Richter Johann
The Johns Hopkins University
LandOfFree
Chemoprotective isothiocyanates does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Chemoprotective isothiocyanates, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chemoprotective isothiocyanates will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1137409