77896-32-3Relevant academic research and scientific papers
Synthesis and antiinflammatory activity of 7-methanesulfonylamino-6- phenoxychromones. Antiarthritic effect of the 3-formylamino compound (T-614) in chronic inflammatory disease models
Inaba, Takihiro,Tanaka, Keiichi,Takeno, Ryuko,Nagaki, Hideyoshi,Yoshida, Chosaku,Takano, Shuntaro
, p. 131 - 139 (2007/10/03)
A group of derivatives of 7-methanesulfonylamino-6-phenoxychromone (1) at the pyrone and phenoxy rings was synthesized starting with 4-chloro-3- nitroanisole and evaluated against acute and chronic inflammations in oral administration in animals. Significant potency in the rat models of carrageenin-induced edema (CPE) and adjuvant-induced arthritis (AA) was realized with 2'-fluoro and 2',4'-difluoro derivatives (9a and 9d), and 3- formylamino derivative (19a) and its 2'-fluoro and 2',4'-difluoro compounds (22a and 22d), displaying AA therapeutic effect of ED40=2.5-7.1 mg/kg/d for 7 d and AA prophylactic effect of 53-70% inhibition at the dosage of 3 mg/kg/d for 22 d. To identify a candidate for further pharmacological study, the five compounds were subjected to evaluation of their gastro-ulcerogenic liability, leading to selection of the fluorine-free compound 19a which did not cause acute ulceration at 300 mg/kg in oral administration in rats. Compound 19a (ED40=3.6 mg/kg in established AA) possessed good therapeutic efficacy against type II collagen-induced arthritis in DBA/1J mice with doses of 30 and 100 mg/kg, suggesting the development of 19a (designated T-614) as a prospective disease-modifying antirheumatic agent. In addition, a preparative-scale synthetic route to T-614 has been established.
Spirodienones. Part 2. The Synthesis of Some Heterocyclic Spirodienones by Phenolic Coupling
Coutts, Ian G. C.,Hamblin, Michael R.,Welsby, Sheila E.
, p. 493 - 497 (2007/10/02)
The oxidation with active manganese dioxide of a series of 2,4'-dihydroxydiphenyl ethers to the corresponding p-benzoquinone monoacetals (1,3-benzodioxole-2-spirocyclohexadien-4'-ones) is described; among the dienones prepared were monoacetals of nitro-p-benzoquinone and of p-fluoranil.Attempted ether formation with 2,6-di-t-butyl-4-bromophenol and either 2- or 3-methoxyphenol failed, small quantities of unsymmetric biphenyls being formed in a novel arylation reaction.A spirobenzoxazole can be prepared by oxidation of a 2,4'-dihydroxydiphenylamine.Substituent effects in the hydrolysis of derived spirodienols have been observed.
