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• W2108767572 abstract "A series of 5-aryl-1,2-dithiolethiones and 5-aryl-1,2-dithiole-3-ones were investigated as hydrogen sulfide-releasing anti-inflammatory drugs. Generally, phenolic acetophenones were best protected by methoxymethyl groups and the dithiolethione group installed by treatment with carbon disulfide, hexamethyldisilathiane, and hexachloroethane. However, ether-protected acetophenones could be elaborated to β-keto esters and converted to dithiolethiones by treatment with phosphorus pentasulfide and elemental sulfur. Dethionation of dithiolethiones to 1,2-dithiole-3-ones was accomplished by mercury(ii)-promoted hydrolysis. A preliminary investigation of the dithiolethiones and dithiole-3-ones as inhibitors of cyclooxygenases COX-1 and COX-2 is discussed. Dithiolethiones bearing a 5-(2,6-di-tert-butyl-4-hydroxyphenyl) or 5-(2,6-di-tert-butyl-4-methoxyphenyl) substituent were the most effective inhibitors of COX-2 and displayed excellent selectivity against COX-1, comparable with rofecoxib, a representative coxib. It is shown that uncatalyzed hydrolysis of the thiocarbonyl group to release hydrogen sulfide leads to the corresponding carbonyl compound, and these carbonyl compounds are moderate COX-2 selective inhibitors." @default.
• W2108767572 created "2016-06-24" @default.
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• W2108767572 date "2010-01-01" @default.
• W2108767572 modified "2023-09-27" @default.
• W2108767572 title "Synthesis and Preliminary Pharmacological Evaluation of Aryl Dithiolethiones with Cyclooxygenase-2-Selective Inhibitory Activity and Hydrogen Sulfide-Releasing Properties" @default.
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• W2108767572 doi "https://doi.org/10.1071/ch09517" @default.
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