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Abstract Design, synthesis, biological evaluation and molecular docking studies of a novel class of N-sulfonyl aminated pyridones using N-cyanoacetoarylsulfonylhydrazide as a versatile precursor The synthetic strategy adopted for producing the target 2-pyridone compounds are represented in schemes 1-4. This part of work focused on the key compound bearing sulfonamide moiety, which was used as potential precursor for synthesis of the novel series of N-sulfonylaminopyrid-2-ones tagged either a benzothiazole or benzoimidazole ring. The key compound, N-cyanoacetoarylsulfonylhydrazide was afforded via a convenient reaction that was developed earlier of cyanoacetohydrazide with arylsulfonyl chloride. The reaction of N-cyanoacetoarylsulfonylhydrazide 4a,b with 2-(benzo[d]thiazol-2-yl)-3,3-bis(alkylthio)-acrylonitrile 3 in the presence of potassium hydroxide in dry DMF produced an adduct for which four possible isomeric structures were considered as was shown in scheme 1. The X-ray crystal structure of the newly synthesized 2-(benzo[d]thiazol-2-yl)-3,3-bis(ethylthio)-acrylonitrile 3b has been dertermined. The X-ray crystal structure of 8b confirmed the presence of the compound in the solid state. The analytical and spectral data of compounds 8a-d were in consistent with their proposed structure. |