Synthesis And Bioactivity Research Of Thiochroman-4-ones Derivatives

It has been reported that thiochroman-4-ones derivatives have broad biological activities, which include a sulfur atom in their molecule structures. In this paper, our main work is to design and synthesize new thiochroman-4-one derivatives, furthermore to evaluate their bioactivities.Fourty benzothiopyrano[4,3-c]pyrazole derivatives, eighteen 6H-thiochromeno [4,3-d][1,2,4]triazolo[1,5-a]pyrimidine derivatives, three 6H-thiochromeno[3,4-e][1,2,4] triazolo[1,5-a]pyrimidine derivatives and three [1,2,4]triazolo[1,5-a]pyrimidine derivatives were designed and synthesized, furthermore their antifungal and anticancer acticities in vitro were evaluated. Pharmacological screening result showed that:1.50% of benzothiopyrano[4,3-c]- pyrazole derivatives had a certain antifungal activity in vitro to tested fungi, and 80% of these had anticancer activity, But the bioactivity difference of cis- and trans- isomer had not been observed; 2.7,12-dihydro-6H-thiochromeno[4,3-d] [1,2,4]triazolo[1,5-a]pyrimidines had antifungal and anticancer activities in vitro, however 6H-thiochromeno[4,3-d][1,2,4]- triazolo[1,5-a]pyrimidines had not antifungal activity; 3. 6H-thiochromeno-[3,4-e][1,2,4]triazolo[1,5-a]pyrimidine and [1,2,4]triazolo[1,5-a]pyrimidine derivatives had antifungal activity, but not anticancer activity.It was found that 7,12-dihydro-6H-thiochromeno[4,3-d][1,2,4]triazolo[1,5-a]pyrimi-dines and 6H-thiochromeno[4,3-d][1,2,4]triazolo[1,5-a]pyrimidines were simultaneously produced in the cyclocondensation reactions of 3-amino-1,2,4-triazole withα,β-unsaturated ketones, which had not been reported in the literature. And the cyclocondensation reaction was regioselective, and only the 2-N atom of triazole could make the reaction under the experimental conditions. The dihydropyrimidines could be directly converted into pyrimi-dines at 190℃without any dehydrogenizing reagent.