2-{[1-phenyl-3-(4-methoxyphenyl)pyrazol-4-yl]methylenehydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid | 1610618-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-{[1-phenyl-3-(4-methoxyphenyl)pyrazol-4-yl]methylenehydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid
• 英文别名: 2-(4-(1-phenyl-3-4-methoxyphenyl-pyrazol-4-yl)methylene-2-hydrazolyl)-1,3-thiazolidin-5-yl-acetic acid
• CAS: 1610618-61-5
• 化学式: C₂₂H₁₉N₅O₄S
• 分子量: 449.49
• InChiKey: GAOLYJGRILFYKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  118.17
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  3-(4-甲氧基苯基)-1-苯基-1H-吡唑-4-甲醛 以 乙醇 、 甲苯 为溶剂， 反应 4.0h， 生成 2-{[1-phenyl-3-(4-methoxyphenyl)pyrazol-4-yl]methylenehydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid
  参考文献：
  名称：

  Synthesis and antihyperglycemic evaluation of new 2-hydrazolyl-4-thiazolidinone-5-carboxylic acids having pyrazolyl pharmacophores

  摘要：

  In the search of new antihyperglycemic agents and following rational approach of drug designing here new 2-hydrazolyl-4-thiazolidinone-5-carboxylic acids (4a-g) with pyrazolyl pharmacophore have been synthesized via thia Michael addition reaction of 1-((3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene) thiosemicarbazides (3a-g) with maleic anhydride. The required precursors, (3a-g) were obtained by condensing known 3-(4-substituted phenyl)-1-phenyl-1H-pyrazole-4-carbaldehydes (1a-g) with thiosemicarbazide in ethanol. The newly synthesized compounds (4a-g) have been evaluated for the antihyperglycemic activity in sucrose loaded rat model and among these compounds 4d, 4f and 4g have displayed significant antihyperglycemic activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.064

文献信息

• Baker’s yeast catalyzed one-pot synthesis of bioactive 2-[benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acids
  作者：Anusaya S. Chavan、Arun S. Kharat、Manisha R. Bhosle、Ramrao A. Mane

  DOI：10.1515/hc-2017-0130

  日期：2018.4.25

  substituted derivatives of 2-hydrazono-4-thiazolidinone-5-acetic acids 4a–j and 6a–g by cyclocondensation of aryl/pyrazolyl aldehyde, thiosemicarbazide and maleic anhydride in acetonitrile in the presence of readily available whole cell biocatalyst, baker’s yeast (Saccharomyces cerevisiae). The reaction is enhanced by ultrasonication.

  摘要 通过芳基/吡唑醛、氨基硫脲和马来酸酐的环缩合反应，开发了一种有效且简单的一锅法，用于合成 2-hydrazono-4-thiazolidinone-5-乙酸 4a-j 和 6a-g 的取代衍生物。在容易获得的全细胞生物催化剂、面包酵母（Saccharomyces cerevisiae）存在下使用乙腈。通过超声处理增强反应。