Synthesis of indole thiazole compounds as ligands for the Ah...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C548S146000, C548S200000, C548S215000, C548S237000, C548S300100, C548S312100

Reexamination Certificate

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11286537

ABSTRACT:
A method of synthesizing aromatic ketone compositions of formula I comprising the step of introducing a double bond into the 5 membered ring of the 4,5-dihydro-1,3-azoles moiety of formula II is disclosed. A method of synthesizing aromatic ketone compositions of formula I comprising the step of ring synthesis of the tetrahydro-1,3-azoles of formula XI is also disclosed.

REFERENCES:
patent: 3285931 (1966-11-01), Huisgen
patent: 5366685 (1994-11-01), Prochaska et al.
patent: 6323228 (2001-11-01), BaMaung et al.
patent: 6743919 (2004-06-01), Koya et al.
patent: 6916834 (2005-07-01), DeLuca et al.
patent: 7002019 (2006-02-01), DeLuca et al.
Adachi J, et al., “Indirubin and indigo are potent aryl hydrocarbon receptor ligand present in human urine,” J. Biol. Chem. 276:31475-31478 (2001).
Chen I, et al., “Indole-3-carbinol and diindolylmethane as aryl hydrocarbon (Ah) receptor agonists and antagonists in T47D human breast cancer cells,” Biochem. Pharmacol. 51: 1069-1076 (1996).
Chen Y, et al., “Regulation of CYP1A1 by indolo[3,2-b]carbazole in murine hepatoma cells,” J. Biol. Chem. 270:22548-22555 (1995).
Cheung Y, et al., “Interation with the aromatic hydrocarbon receptor, CYP1A induction, and mutagenicity of a series of diaminotoluences—implications for their carcinogenicity,” Toxicol. Appl. Pharmacol. 139:203-211 (1996).
Chunchatprasert L, et al., “A New Synthetic Route to Pyrrolo[3,2-b]carbozoles, 1H-Benzofuro[3,2-f]indoles and 1H-[1]Benzothieno[2,3-f]indoles,” J. Chem. Soc. Perkin Trans. 1779-1783 (1992).
Chunchatprasert L & Shannon P, “Further Observations on and Novel Products from Acid-catalyzed Indole-Pyrrole Condensations: Formation of Pyrrole[2,3-b] carbazoles,” J. Chem. Soc. Perkin Trans. pp. 1765-1772 (1994).
Dharmasena P, et al., “Antitumour Heterocycles. Part 12. The Synthesis of New Hydroxypyrrolocarbazoles and Hydroxypyridocarbaoles,” J. Chem. Research 12-13 (1996).
Garrison P, et al., “Species-specific recombinant cell lines as bioassay systems for the detection of 2,3,7,8-tetrachlorodibenzo-p-dioxin-like chemicals,” Fund. Appl. Toxicol. 30:194-203 (1996).
Hankinson O, “The Aryl Hydrocarbon Receptor Complex,” Annu. Rev. Pharmacol. Toxicol. 35:307-340 (1995).
Heath-Pagliuso S, et al., “Activation of the Ah receptor by tryptophan and tryptophan metabolites,” Biochem. 37:11508-11515 (1998).
Jellinck P, et al., “Ah Receptor Binding Properties of Indole Carbinols and Induction of Hepatic Estradiol Hydroxylation,” Biochem. Pharmacol. 45:1129-1136 (1993).
Lee I, et al., “Transcriptional induction of the cytochrome P4501A1 gene by a thiazolium compound, YH439,” Mol. Pharmacol. 49:980-988 (1996).
Liu R, et al. “Regulation of [Ah] gene battery enzymes and glutathione levels by 5,10-dihydroindeno[1,2,-b]indole in mouse hepatoma cell lines,” Carcinogenesis 15:2347-2352 (1994).
Phillips A, et al., “Synthesis of Functionalized Oxazolines and Oxazoles with DAST and Deoxo-Fluor,” Org. Lett. 2:1165-1168 (2000).
Poellinger L, “Regulation of Intracellular Dioxin (Aryl Hydrocarbon) Receptor Function by Dietary Indole Derivatives, Hormonally Active Agents,” in Food Symposium 121-127 (1998).
Poellinger L, “Mechanistic aspects—the dioxin (aryl hydrocarbon) receptor,” Food Addit. Contam. 17:261-266 (2000).
Poland A & Glover E, “Chlorinated dibenzo-p-dioxin: Potent inducers of δ-aminolevulinic acid synthetase and aryl hydrocarbon hydroxylase. II. A study of the structure-activity relationship,” Mol. Pharmacol. 9:736-747 (1973).
Rannug A, et al. “Certain photooxidized derivatives of tryptophan bind with very high affinity to the Ah receptor and are likely to be endogenous signal substances,” J. Biol. Chem. 262:15422-15427 (1987).
Song J, et al., “A ligand for the aryl hydrocarbon receptor isolated from lung,” Proc. Natl. Acad. Sci. USA 99:14694-14699 (2002).
Susilo R, et al., “Formation of Thiazolidine-4-Carboxylic Acid Represents a Main Metabolic Pathway of 5-Hydroxytryptamine in Rat Brain,” J. Neurochem. 52:1793-1800 (1989).
Schaldach, C, et al., “Lipoxin A(4): A new class of ligand for the Ah receptor,” Biochemistry 38:7594-7600 (1999).
Sinal C & Bend J, “Aryl hydrocarbon receptor-dependent induction of cyp 1a1 by bilirubin in mouse hepatoma hepa 1c1c7 cells,” Mol. Pharmacol. 52:590-599 (1997).
Stephensen P, et al. “N-methoxyindole-3-carbinol is a more efficient inducer of cytochrome P-450 1A1 in cultured cells than indol-3-carbinol”, Nutr. Cancer 36:112-121 (2000).
Vasiliou V, et al., “Response of [Ah] battery genes to compounds that protect against menadione toxicity,” Biochem. Pharmacol. 50:1885-1891 (1995).
Washburn B, et al., “Brevetoxin-6 (pbtx-6), a nonaromatic marine neurotoxin, is a ligand of the aryl hydrocarbon receptor,” Arc. Biochem. Biophy. 343:149-156 (1997).
Whitlock J, et al., “Genetic and molecular aspects of 2,3,7,8-tetrachlorodibenzo-p-dioxin action,” Ann. Rev. Pharmacol. Toxicol. 30:251-277 (1990).

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