一锅法合成硫色满酮杂环衍生物及抗菌活性研究

发布时间：2018-06-21 22:17

本文选题：硫色满酮 + 一锅法　；参考：《河北大学》2014年硕士论文

【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]:Sulfur and ketones are a kind of heterocyclic compounds with high lipid solubility and low water solubility. They have a wide range of physiological and pharmacological activities. It can inhibit the growth of fungi by destroying the cell wall and cell membrane structure and function. In this paper, 19 phenythiazole-thioleno [4o _ 3-c] pyrazole compounds and 15 pyrano [3o _ 2-c] thiopyranes were synthesized by one-pot method based on the modification design of p-thiolone. The structure of the target compounds was confirmed by nuclear magnetic resonance spectroscopy (NMR), carbon spectrum, high resolution mass spectrometry and so on. The antifungal activity of the target compound was tested by double concentration dilution method. Phenylthiazole-thiocereno [4o 3-c] pyrazole was synthesized from substituted phenythiophenol as starting material, and then 19 target products were obtained by one-pot method using 3-aldothiolone, bromoacetophenone and thiosemicarbazone as raw materials. Antifungal experiments in vitro showed that some compounds had good inhibitory activity against Cryptococcus neoformans. The effects of reflux method and ultrasonic method on the yield of the reaction were compared under different solvent and reaction time. The results showed that ethanol was the best solvent under ultrasonic conditions. In this paper, the intermediate product of substituted thiolone was synthesized from substituted phenythiophenol by pyrano [3o 2-c] thiofuran compounds. Fifteen target products were obtained by one-pot method using substituted thiolone, malonitrile and aromatic aldehydes as raw materials. Some compounds have weak inhibitory effect on Cryptococcus neoformans.
【学位授予单位】：河北大学
【学位级别】：硕士
【学位授予年份】：2014
【分类号】：R914

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