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Design and synthesis of novel iminothiazinylbutadienols and divinylpyrimidinethiones as ARE inducers.

ABSTRACT: Novel iminothiazinylbutadienols and divinylpyrimidinethiones were designed and synthesized as analogues of curcumin with its diketone moiety masked as a heterocyclic adduct with thiourea. The chemical stability of these novel heterocyclic compounds was improved as compared to curcumin. They exhibit longer half-lives and do not react with nucleophilic thiols under physiological conditions. In an ARE-luciferase reporter assay, some of these new curcumin analogues are more effective ARE activators than curcumin and isothiocyanates.

SUBMITTER: Chen L

PROVIDER: S-EPMC3936471 | biostudies-other | 2014 Feb

REPOSITORIES: biostudies-other

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Design and synthesis of novel iminothiazinylbutadienols and divinylpyrimidinethiones as ARE inducers.

Chen Lin L Magesh Sadagopan S Wang Hong H Yang Chung S CS Kong Ah-Ng Tony AN Hu Longqin L

Bioorganic & medicinal chemistry letters 20131224 3

Novel iminothiazinylbutadienols and divinylpyrimidinethiones were designed and synthesized as analogues of curcumin with its diketone moiety masked as a heterocyclic adduct with thiourea. The chemical stability of these novel heterocyclic compounds was improved as compared to curcumin. They exhibit longer half-lives and do not react with nucleophilic thiols under physiological conditions. In an ARE-luciferase reporter assay, some of these new curcumin analogues are more effective ARE activators ...[more]

PMID: 24398297

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