文档介绍：毕业论文
(2009年)
课题名称 2-烃硫基硫色酮类抗真菌
化合物的合成研究
专业名称应用化学
学生姓名
学号
指导教师
南京工业大学理学院
2-烃硫基硫色酮类抗真菌化合物的合成研究
摘要
本文根据氮唑类抗真菌药物的作用机制和构效学关系,以其作为先导化合物,利用拼接原理和生物电子等排原理,在其1位N原子上引入具有明显抗真菌活性的硫色酮结构,设计合成了二个全新结构的唑类抗真菌化合物。本文所合成的含硫色酮结构的氮唑化合物,是以1-(2,4-二氟苯基)-2-(1H-氮唑-1-基)乙酮为原料,利用其α氢活性先与二硫化碳缩合,再利用缩合物中巯基的反应活性,在碱性条件下与1-位苯环上的2-氟基团反应而关环成2-巯基硫色酮结构,最后再在巯基上引入取代基而得。目标化合物的合成采用一步法,将反应中的与二硫化碳的缩合、关环成色酮环、Williamson醚合成等三步反应集成到一步完成。实验中采用TLC跟踪来监测各步的反应情况。在化合物合成的缩合和关环反应中,采用较高的反应温度下进行,有利于生成硫色酮的主反应进行。在Williamson醚合成阶段采用室温反应,有利于降低副反应的发生。合成产物可以用熔点测定、元素分析、核磁共振氢谱及质谱方法来对其进行鉴定。
最后得到2-甲硫基-7-氟-3-(1H-1,2,4-三唑-1-基),收率71%:,.:208℃-210℃, 2-巯基-7-氟-3-(1H-1,2,4-三唑-1-基),收率:68%,.:264℃-266℃。
关键词: 硫色酮、缩合反应、成环反应、Williamson反应、抗真菌化合物
Study On The Synthesis of -Sulfur Chromone With Antifungal Activity
ABSTRACT
In this paper, according to azole antifungal agents and the mechanism of structure-activity relationship study, in its capacity as pounds, and biological principles of the use of splicing electronic scheduling principle, one in his introduction of N atoms on a clear antifungal activity of sulfur chromone structure, design and synthesis of the two new structures azole pounds. In this paper, the synthesis of the structure of chromone content pounds, based on 1 - (2,4 - difluorophenyl) -2 - (1H-Benzotriazole -1 - yl) ethyl ketone as raw material, the use of the α hydrogen activity condensation with carbon disulfide, and then the use of condensate in the reaction of sulfhydryl activity, under alkaline conditions with the 1 - position on the benzene ring of 2 - fluoro group cyclization reaction into 2 - mercapto-sulfur chromone structure, then in the introduction of sulfhydryl substituent derived. Synthesis of pounds using one-step, the reaction of condensation with carbon disulfide, ketone cyclization fineness Central, Williamson ether synthesis reaction into three steps in one step. Tracking experiments using TLC to monitor the response of the step-by-step. In the synthesis of condensation and