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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (01): 126-130. 上一篇    下一篇

研究简报

1,3-噻唑烷衍生物的合成、结构及生物活性

翁建全*，沈德隆，谭成侠   

  1. (浙江工业大学化学工程与材料学院 杭州 310032)
  • 收稿日期:2006-02-22 修回日期:2006-06-27 发布日期:2006-12-30
  • 通讯作者: 翁建全

Synthesis, Structure and Biological Activities of1,3-Thiazolidine Derivatives

WENG Jian-Quan*,SHEN De-Long,TAN Cheng-Xia   

  1. (College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310032)
  • Received:2006-02-22 Revised:2006-06-27 Published:2006-12-30
  • Contact: WENG Jian-Quan

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925

被引次数

17

为了寻找新的含噻唑杂环的先导化合物, 利用2-取代-1,3-噻唑烷1与氯甲酸取代苯基酯2及取代苯基甲酰氯4在三乙胺存在下发生缩合反应, 合成了6个2-取代-1,3-噻唑烷-3-甲酸酯类化合物3和5个N-苯甲酰基-2-取代-1,3-噻唑烷类化合物5, 并利用1H NMR, IR, MS, 元素分析对其结构进行了表征. 用X-ray单晶衍射测定了2-硫代-1,3-噻唑烷-3-甲酸苯酯(3d)和N-苯甲酰基-2-氧代-1,3-噻唑烷(5a)的晶体结构, 证实了氯甲酸酯与2-硫代-1,3-噻唑烷的反应产物为硫酮式结构, 而非硫酯式结构. 初步生物活性试验结果表明, 在试验浓度下部分目标化合物3和5具有一定的杀菌和杀虫活性.

关键词: 生物活性, 2-取代-1, 结构, 3-噻唑烷, 取代苯基甲酰氯, 氯甲酸取代苯基酯

In order to find new thiazole-heterocycle lead compounds, six 2-oxo/thio-1,3-thiazolidine- 3-carboxylates 3 and five N-substituted benzoyl-2-oxo/thio-1,3-thiazolidines 5 were synthesized from a condensation reaction of 2-oxo/thio-1,3-thiazolidine 1 and substituted phenyl chloroformates 2 or substituted benzoyl chlorides 4 in presence of Et3N. Their structures were confirmed by 1H NMR, IR, MS spectra and elemental analysis. The crystal structures of phenyl 2-thiono-1,3-thiazolidine-3-carboxylate (3d) and N-benzoyl-2- oxo-1,3-thiazolidine (5a) were determined by X-ray diffraction analysis, and the structure of the condensation products of 2-thiono-1,3-thiazolidine with substituted phenyl chloroformates was proved to be 2-thiono-1,3-thiazolidine-3-carboxylate rather than the ester of mercaptothiazoline. The preliminary bioassay showed that compounds 3 and 5 exhibited certain fungicidal and insecticidal activities.

Key words: substituted phenyl chloroformate, biological activity, substituted benzoyl chloride, structure, 2-oxo/thio-1,3-thiazolidine