5-pentylidenethiazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-pentylidenethiazolidine-2,4-dione
• 英文别名: (5Z)-5-pentylidene-1,3-thiazolidine-2,4-dione
• 化学式: C₈H₁₁NO₂S
• 分子量: 185.247
• InChiKey: MEIIYCOOWRJJKA-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-pentylidenethiazolidine-2,4-dione 在 氢溴酸 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.17h， 生成 N-(allyloxy)-2-(2,4-dioxo-5-pentylidenethiazolidin-3-yl)acetamide
  参考文献：
  名称：

  Novel thiazolidinedione-hydroxamates as inhibitors of Mycobacterium tuberculosis virulence factor Zmp1

  摘要：

  Zinc metalloprotease 1 (Zmp1) is an extracellular enzyme, which has been found essential for the intracellular survival and pathogenesis of Mycobacterium tuberculosis. In this work, we designed and synthesized a series of novel thiazolidinedione-hydroxamates and evaluated in silica their drug-likeness behavior. Then, their inhibitory properties towards a recombinant Zmp1 from Mycobacterium tuberculosis were analyzed by MALDI-TOF MS. Nine of the tested compounds were found to inhibit the enzymatic reaction more effectively than the generic metalloprotease inhibitor phosphoramidon. Furthermore, the synthesized thiazolidinedione-hydroxamate hybrids were evaluated for their in vitro antimycobacterial activity and acute cytotoxicity using whole-cell assays. Results showed that none of the hybrids exhibited acute cytotoxicity against RAW264.7 macrophages. Whereas extracellular antimycobacterial activity was limited, RAW264.7 macrophage infection results showed that a majority of the hybrids inhibited the intracellular growth of Mycobacterium tuberculosis at a concentration of 100 and 10 mu M. The thiazolidinedione-hydroxamate compound 2n was considered to be the best candidate of the evaluated library. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111812
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 1-羟基戊烷-1-磺酸钠 在 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以50%的产率得到5-pentylidenethiazolidine-2,4-dione
  参考文献：
  名称：

  乙酸酐促进的2,4-噻唑烷二酮与醛的亚硫酸氢盐加成物的一锅缩合

  摘要：

  我们描述了一种简单有效的一锅法，用于直接与乙酸酐催化的2,4-噻唑烷二酮缩合芳族醛的亚硫酸氢盐加合物。这项研究的两个主要亮点是亚硫酸氢盐加合物与2,4-噻唑烷二酮在非水介质中的一锅缩合，以及使用实验设计来了解和优化反应条件。然后使用其他活性亚甲基化合物（如丙二腈）推广该方法。

  DOI：

  10.1016/j.tetlet.2014.06.082

文献信息

• Novel thiazolidinedione-hydroxamates as inhibitors of Mycobacterium tuberculosis virulence factor Zmp1
  作者：Veronika Šlachtová、Marek Šebela、Eveline Torfs、Lauren Oorts、Davie Cappoen、Karel Berka、Václav Bazgier、Lucie Brulíková

  DOI：10.1016/j.ejmech.2019.111812

  日期：2020.1

  Zinc metalloprotease 1 (Zmp1) is an extracellular enzyme, which has been found essential for the intracellular survival and pathogenesis of Mycobacterium tuberculosis. In this work, we designed and synthesized a series of novel thiazolidinedione-hydroxamates and evaluated in silica their drug-likeness behavior. Then, their inhibitory properties towards a recombinant Zmp1 from Mycobacterium tuberculosis were analyzed by MALDI-TOF MS. Nine of the tested compounds were found to inhibit the enzymatic reaction more effectively than the generic metalloprotease inhibitor phosphoramidon. Furthermore, the synthesized thiazolidinedione-hydroxamate hybrids were evaluated for their in vitro antimycobacterial activity and acute cytotoxicity using whole-cell assays. Results showed that none of the hybrids exhibited acute cytotoxicity against RAW264.7 macrophages. Whereas extracellular antimycobacterial activity was limited, RAW264.7 macrophage infection results showed that a majority of the hybrids inhibited the intracellular growth of Mycobacterium tuberculosis at a concentration of 100 and 10 mu M. The thiazolidinedione-hydroxamate compound 2n was considered to be the best candidate of the evaluated library. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Acetic anhydride-promoted one-pot condensation of 2,4-thiazolidinedione with bisulfite adducts of aldehydes
  作者：Sandeep Mohanty、Amrendra Kumar Roy、Vinay K.P. Kumar、Sandeep G. Reddy、Arun Chandra Karmakar

  DOI：10.1016/j.tetlet.2014.06.082

  日期：2014.8

  We describe a simple and efficient one-pot method for condensing bisulfite adducts of aromatic aldehydes directly with 2,4-thiazolidinedione catalyzed by acetic anhydride. The two main highlights of this study are the one-pot condensation of bisulfite adducts with 2,4-thiazolidinedione in non-aqueous media and the use of Design of Experiment to understand and optimize the reaction conditions. This

  我们描述了一种简单有效的一锅法，用于直接与乙酸酐催化的2,4-噻唑烷二酮缩合芳族醛的亚硫酸氢盐加合物。这项研究的两个主要亮点是亚硫酸氢盐加合物与2,4-噻唑烷二酮在非水介质中的一锅缩合，以及使用实验设计来了解和优化反应条件。然后使用其他活性亚甲基化合物（如丙二腈）推广该方法。