3-(4-Hydroxyphenyl)-2-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)propanoic acid | 305378-01-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(4-Hydroxyphenyl)-2-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)propanoic acid
• 英文别名: 3-(4-hydroxyphenyl)-2-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)propanoic acid
• CAS: 305378-01-2
• 化学式: C₁₂H₁₁NO₄S₂
• 分子量: 297.356
• InChiKey: MJXXLOVNUUHQQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-Hydroxyphenyl)-2-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)propanoic acid 、 香草醛 在 N-甲基哌嗪 、 ammonium acetate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以76%的产率得到(+/-)-2-((Z)-5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-(4-hydroxyphenyl)propanoic acid
  参考文献：
  名称：

  Discovery of novel glitazones incorporated with phenylalanine and tyrosine: Synthesis, antidiabetic activity and structure–activity relationships

  摘要：

  We report a series of new glitazones incorporated with phenylalanine and tyrosine. All the compounds were tested for their in vitro glucose uptake activity using rat-hemidiaphragm, both in presence and absence of insulin. Six of the most active compounds from the in vitro screening were taken forward for their in vivo triglyceride and glucose lowering activity against dexamethazone induced hyperlipidemia and insulin resistance in Wistar rats. The liver samples of rats that received the most active compounds, 23 and 24, in the in vivo studies, were subjected to histopathological examination to assess their short term hepatotoxicity. The investigations on the in vitro glucose uptake, in vivo triglyceride and glucose lowering activity are described here along with the quantitative structure-activity relationships. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2012.08.002
• 作为产物：
  描述：

  DL-酪氨酸 在 氨 、 水 作用下， 以 水 为溶剂， 反应 17.0h， 生成 3-(4-Hydroxyphenyl)-2-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)propanoic acid
  参考文献：
  名称：

  Discovery of novel glitazones incorporated with phenylalanine and tyrosine: Synthesis, antidiabetic activity and structure–activity relationships

  摘要：

  We report a series of new glitazones incorporated with phenylalanine and tyrosine. All the compounds were tested for their in vitro glucose uptake activity using rat-hemidiaphragm, both in presence and absence of insulin. Six of the most active compounds from the in vitro screening were taken forward for their in vivo triglyceride and glucose lowering activity against dexamethazone induced hyperlipidemia and insulin resistance in Wistar rats. The liver samples of rats that received the most active compounds, 23 and 24, in the in vivo studies, were subjected to histopathological examination to assess their short term hepatotoxicity. The investigations on the in vitro glucose uptake, in vivo triglyceride and glucose lowering activity are described here along with the quantitative structure-activity relationships. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2012.08.002

文献信息

• Identification of<i>para</i>-Substituted Benzoic Acid Derivatives as Potent Inhibitors of the Protein Phosphatase Slingshot
  作者：Kang-shuai Li、Peng Xiao、Dao-lai Zhang、Xu-Ben Hou、Lin Ge、Du-xiao Yang、Hong-da Liu、Dong-fang He、Xu Chen、Ke-rui Han、Xiao-yuan Song、Xiao Yu、Hao Fang、Jin-peng Sun

  DOI：10.1002/cmdc.201500454

  日期：2015.12

  Slingshot‐inhibiting activities have therapeutic potential against cancers or infectious diseases. However, only a few Slingshot inhibitors have been investigated and reported, and their cellular activities have not been examined. In this study, we identified two rhodanine‐scaffold‐based para‐substituted benzoic acid derivatives as competitive Slingshot inhibitors. The top compound, (Z)‐4‐((4‐((4‐oxo‐2

  弹弓蛋白形成一小部分的双特异性磷酸酶，它们通过cofilin和Lim激酶（LIMK）的去磷酸化来调节细胞骨架的动力学。具有弹弓抑制活性的小型化合物具有治疗癌症或传染病的潜力。但是，仅研究和报道了几种弹弓抑制剂，尚未检查它们的细胞活性。在这项研究中，我们确定了两种基于罗丹宁骨架的对位取代苯甲酸衍生物作为竞争性弹弓抑制剂。顶部化合物（Z）-4-（（（4-（（4-氧代-2--2-硫代氧-3-（邻甲苯基）噻唑烷酮-5亚叉基）甲基）苯氧基）甲基）苯甲酸（D3）抑制常数（ķ我）约为4μm，并且在一组其他磷酸酶上显示出选择性。此外，化合物D3抑制神经生长因子（NGF）或血管紧张素II刺激后的细胞迁移和cofilin去磷酸化。因此，我们新近确定的弹弓抑制剂为开发以弹弓为目标的疗法提供了起点。
• Rhodanine Derivatives Containing 5‐Aryloxypyrazole Moiety as Anti‐inflammatory and Anticancer Agents
  作者：Lin Zhu、Chao Ye、Shuang Chen、Yuqi Fang、Yu Zhang、Tianyi Zhang

  DOI：10.1002/cbdv.202301844

  日期：2024.2

  In this study, a series of rhodanine derivatives containing 5-aryloxypyrazole moiety were identified as potential agents with anti-inflammatory and anticancer properties. Most of the synthesized compounds demonstrated anti-inflammatory and anticancer activity. Notably, compound 7 g (94.1 %) exhibited significant anti-inflammatory activity compared with the reference drugs celecoxib (52.5 %) and hydrocortisone

  在这项研究中，一系列含有5-芳氧基吡唑部分的绕丹宁衍生物被鉴定为具有抗炎和抗癌特性的潜在药物。大多数合成的化合物都表现出抗炎和抗癌活性。值得注意的是，与参考药物塞来昔布（52.5%）和氢化可的松（79.4%）相比，化合物7g （94.1%）表现出显着的抗炎活性。不同浓度的化合物7g以剂量依赖性方式有效抑制一氧化氮(NO)的产生。 Western blot结果显示，化合物7g可以阻止LPS诱导的巨噬细胞炎症介质的表达。酶联免疫吸附测定 (ELISA) 测定表明7 g是一种有前途的化合物，能够阻断 COX-2 的下游信号传导。总之，这些发现表明化合物7 g可能是进一步研究的有希望的候选者。
• Discovery of novel glitazones incorporated with phenylalanine and tyrosine: Synthesis, antidiabetic activity and structure–activity relationships
  作者：B.R. Prashantha Kumar、Nasir R. Baig、Sai Sudhir、Koyal Kar、M. Kiranmai、M. Pankaj、Nanjan M. Joghee

  DOI：10.1016/j.bioorg.2012.08.002

  日期：2012.12

  We report a series of new glitazones incorporated with phenylalanine and tyrosine. All the compounds were tested for their in vitro glucose uptake activity using rat-hemidiaphragm, both in presence and absence of insulin. Six of the most active compounds from the in vitro screening were taken forward for their in vivo triglyceride and glucose lowering activity against dexamethazone induced hyperlipidemia and insulin resistance in Wistar rats. The liver samples of rats that received the most active compounds, 23 and 24, in the in vivo studies, were subjected to histopathological examination to assess their short term hepatotoxicity. The investigations on the in vitro glucose uptake, in vivo triglyceride and glucose lowering activity are described here along with the quantitative structure-activity relationships. (C) 2012 Elsevier Inc. All rights reserved.