2-[(2E)-4-oxo-2-(thiophen-2-ylmethylidenehydrazinylidene)-1,3-thiazolidin-5-yl]acetic acid | 21926-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-[(2E)-4-oxo-2-(thiophen-2-ylmethylidenehydrazinylidene)-1,3-thiazolidin-5-yl]acetic acid
• CAS: 21926-65-8
• 化学式: C₁₀H₉N₃O₃S₂
• 分子量: 283.332
• InChiKey: FALAOKLSBBVLDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 马来酸酐 、 氨基硫脲 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 以33%的产率得到2-[(2E)-4-oxo-2-(thiophen-2-ylmethylidenehydrazinylidene)-1,3-thiazolidin-5-yl]acetic acid
  参考文献：
  名称：

  Synthesis of 2-Hydrazolyl-4-Thiazolidinones Based on Multicomponent Reactions and Biological Evaluation Against Trypanosoma Cruzi

  摘要：

  A series of 18 novel 2-hydrazolyl-4-thiazolidinones-5-carboxylic acids, amides and 5,6-alpha,beta-unsaturated esters were synthesized, and their in vitro activity on cruzipain and T. cruzi epimastigotes was determined. Some agents show activity at 37 mu m concentration in the enzyme assay. Computational tools and docking were used to correlate the biological response with the physicochemical parameters of the compounds and their cruzipain inhibitory effects.

  DOI：

  10.1111/j.1747-0285.2010.01071.x

文献信息

• Microwave-assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones
  作者：Cecilia Saiz、Chiara Pizzo、Eduardo Manta、Peter Wipf、S. Graciela Mahler

  DOI：10.1016/j.tetlet.2008.12.020

  日期：2009.2

  A tandem method for the synthesis of 2-hydrazolyl-4-thiazolidinones (5) from commercially available materials in a 3-component reaction has been developed. The reaction connects aldehydes, thiosemicarbazides, and maleic anhydride, effectively assisted by microwave irradiation. The synthesis of a new type of compound, 2-hydrazolyl-5,5-diphenyl-4-thiazolidinone (7), obtained by treatment of thiosemicarbazone with benzil in basic media is also reported. HOMO/LUMO energies, orbital coefficients, and charge distribution were used to explain the proposed reaction mechanism. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of 2-Hydrazolyl-4-Thiazolidinones Based on Multicomponent Reactions and Biological Evaluation Against Trypanosoma Cruzi
  作者：Chiara Pizzo、Cecilia Saiz、Alan Talevi、Luciana Gavernet、Pablo Palestro、Carolina Bellera、Luis Bruno Blanch、Diego Benítez、Juan J. Cazzulo、Agustina Chidichimo、Peter Wipf、S. Graciela Mahler

  DOI：10.1111/j.1747-0285.2010.01071.x

  日期：2011.3

  A series of 18 novel 2-hydrazolyl-4-thiazolidinones-5-carboxylic acids, amides and 5,6-alpha,beta-unsaturated esters were synthesized, and their in vitro activity on cruzipain and T. cruzi epimastigotes was determined. Some agents show activity at 37 mu m concentration in the enzyme assay. Computational tools and docking were used to correlate the biological response with the physicochemical parameters of the compounds and their cruzipain inhibitory effects.