新型含1,3,4-噻二唑的硫色满酮衍生物的合成及其抗真菌活性  

Synthesis and Antifungal Activities of Novel Thiochromanone Derivatives Containing 1,3,4-Thiadiazole

作　　者：梁国超[1,2] 周冠[1,2] 钟一凡[1,2] 韩晓燕[1,2] 宋亚丽[1,2] 

机构地区：[1]河北大学药学院河北省药品质量控制重点实验室,河北保定071002 [2]河北大学教育部药物化学与分子诊断重点实验室,河北保定071002

出　　处：《合成化学》2015年第12期1100-1105,1110,共7页Chinese Journal of Synthetic Chemistry

基　　金："重大新药创制"国家科技重大专项(2012ZX09103-101-057);河北省药物质量分析控制重点实验室开放基金资助课题;河北大学自然科学基金资助项目(2010-194)

摘　　要：以取代苯硫酚和顺丁烯二酸酐为原料,经迈克尔加成反应制得2-羧基-硫色满酮衍生物(2a^2d);2a^2d分别与氨基硫脲反应制得2-(5-氨基-1,3,4-噻二唑-2-基)硫色满-4-酮衍生物(3a^3d);3a^3d与酰氯经酰化反应合成了14个新型的含1,3,4-噻二唑的硫色满酮衍生物(5a^5n),其结构经1H NMR,^(13)C NMR和HRESI-MS表征。采用微量稀释法测定了5a^5n的抗真菌活性。结果表明:部分化合物对絮状表皮癣菌和总状毛霉菌有较好的抑制活性,优于阳性对照药氟康唑。4-Thiochromane-2-carboxylic acid derivatives（ 2a - 2d） were prepared by Michael addition reaction of substituted thiophenol with maleic anhydride. 2-（ 5-amino-1,3,4-thiadiazol-2-yl） thiochroman-4-one derivatives（ 3a - 3d） were prepared by acylation reaction of 2a - 2d with thiosemicarbazide,respectively. Fourteen novel thiochromanone derivatives（ 5a - 5n） containing 1,3,4-thiadiazole were synthesized by reaction of 3a - 3d with acyl chloride. The structures were characterized by ^1 H NMR,^13 C NMR and HR-ESI-MS. The antifungal activities of 5a - 5n were investigated by micro dilution method. The results showed that some derivatives exhibited better antifungal activities on Epidermophyton floccosum and Mucor racemosus than Fluconazole.

关 键 词：硫色满酮 1 3 4-噻二唑 合成 抗真菌活性 

分 类 号：O626[理学—有机化学] O621.3[理学—化学]