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一锅法合成硫色满酮杂环衍生物及抗菌活性研究
One Pot Synthesis and Antifungal Activites of Thiochromanones Derivatives
【作者】 杨涛；
【作者基本信息】 河北大学 ， 药物化学， 2014， 硕士
【摘要】 硫色满酮类化合物是一类高脂溶低水溶性的含硫杂环化合物，具有广泛的生理药理活性，它通过对真菌细胞壁和细胞膜结构和功能的破坏，达到抑制真菌生长的目的。本文基于对硫色满酮的修饰设计并一锅法合成了19个苯基噻唑-硫色烯并[4,3-c]吡唑类化合物和15个吡喃并[3,2-c]噻喃类化合物。所得到的目标化合物结构由核磁共振氢谱及碳谱、高分辨质谱等确证。并采用二倍浓度稀释法对目标化合物的抗真菌活性进行了测试。苯基噻唑-硫色烯并[4,3-c]吡唑类化合物以取代苯硫酚为起始原料，合成中间产物3-醛基硫色满酮，再以3-醛基硫色满酮，溴代苯乙酮和氨基硫脲为原料一锅法得到19个目标产物。体外抗真菌实验表明部分化合物对新生隐球菌有较好的抑制活性。对比了不同溶剂和反应时间条件下回流法和超声法对该反应产率的影响，结果表明在超声条件下以乙醇为溶剂反应产物的产率最高。吡喃并[3,2-c]噻喃类化合物以取代苯硫酚为原料，合成中间产物取代硫色满酮。再以取代硫色满酮，丙二腈和芳醛为原料一锅法得到15个目标产物。部分化合物对新生隐球菌有微弱的抑制作用。
【Abstract】 Thiochroman-4-one derivatives are a kind of high lipophilicity and low hydrophilcityheterocyclic compounds with Sulfur atom which has a wide range of biological activities. Itcan damage the structure and the function of the cell membrane and the wall of fungi, leadingfungi to death.19thiochromeno[4,3-c]pyrazole derivatives and15pyrano[3,2-c]thiochromanderivatives based on thiochroman-4-one were designed and synthesized in one-pot. Thestructures of new synthesized compounds were characterized by HRMS,1H NMR, and13CNMR. Antifungi activities of the target compounds were tested using double dilution method.3-carbaldehyde-thiochromanone were synthesized from substituted thiophenol as thestarting material. Then using the3-carbaldehyde-thiochromanone, phenacyl bromide andthiosemicarbazide as raw material react in order to get the target compounds.19targetcompounds were tested in vitro antifungal activity and the test results showed that some of thecompounds exhibited antifungal activity against C. Neoformans. And we compared the effectsof different solvent and reaction time for the yields of this reaction under reflux andultrasonic.Thiochromanones were synthesized through substituted reaction and cyclization reactionfrom the starting material thiophenol. Then using the substited thiochromanones,malononitrile and aromatic aldehydes as raw material to get the target compounds.15targetcompounds were tested in vitro antifungal activity and the test results showed that some of thecompounds exhibited weak antifungal activity against C. Neoformans.