二环杂环化合物热重排反应的意外副产物7-甲硫基-4-甲基-2H-色烯-2-酮及其抗HBV活性

Accidentally obtained by-product from the thermal rearrangement of a bicyclic hetercyclic compound and its anti-HBV activity

目的利用 7 二甲基硫代氨甲酰氧基 4 甲基 2H 色烯 2 酮 (3)高温下的热重排反应制备 7 二甲基氨甲酰基硫基 4 甲基 2H 色烯 2 酮 (5 )。方法热重排反应。结果除了得到期望的 7 二甲基氨甲酰基硫基 4 甲基 2H 色烯 2 酮 (5 )产物外 ,还分离得到意外的副产物 7 甲硫基 4 甲基 2H 色烯 2 酮 (7) ,其结构经波谱确证。对该副产物进行抗 HBV生物活性测定 ,显示出显著的抗HBV活性。结论 7 二甲基硫代氨甲酰氧基 4 甲基 2H 色烯 2 酮 (3)在高温下产生 7 甲硫基 4 甲基 2H 色烯 2 酮 (7)副产物 ,未见文献报道 ,并对其产生的机制进行探讨。首次报道了 7 甲硫基 4 甲基 2H 色烯 2 酮 (7)

Aim To prepare 7-dimethylcarbamoy lt hio-4-methyl-2H-chromen-2-one (5)via the therm al rearrangement of 7-dimethylcarbamothioyloxy-4-methyl-2H-chromen-2 -one.Method Thermal rearrangement reaction was used.Res ult Except obtaining the desired product 7-dimethylcarbamoylthio-4-methyl-2H-chromen-2-one (5 ),an unexpected by-product,7-methylthi o-4-methyl-2H-chromen-2-one(7)was isolated fro m the reaction.Its structure wa s identified by spectra.Anti-HBV bioassay demonstrated this by-product has pot ent anti-HBV bioactivity.Conclusion Obtaining such a by-produc t from the thermal rearrangement of 7-dimethylcarbamothioyloxy-4-methyl-2H -chromen-2-one(3)has not been reported in literatur e.The mechanism of its formation was speculated.Moreover,the anti-HBV bioactivi ty of 7-methylthio-4-me thyl-2H-chromen-2-one (7)is reported first.