4-[5-(4-Hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]methylbenzoic acid | 943447-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[5-(4-Hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]methylbenzoic acid
• 英文别名: 4-[[(5Z)-5-[(4-hydroxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]benzoic acid
• CAS: 943447-75-4
• 化学式: C₁₈H₁₃NO₅S
• 分子量: 355.371
• InChiKey: OMKLGAAQSMALAO-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[5-(4-Hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]methylbenzoic acid 、 溴乙酸甲酯 在 potassium carbonate 、 盐酸 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 28.0h， 以84%的产率得到4-[5-(4-Carboxymethoxybenzylidene)-2,4-dioxothiazolidin-3-yl]methylbenzoic acid
  参考文献：
  名称：

  5-Arylidene-2,4-thiazolidinediones as inhibitors of protein tyrosine phosphatases

  摘要：

  4-(5-Arylidene-2,4-dioxothiszolidin-3-yl)methylbenzoic acids (2) were synthesized and evaluated in vitro as inhibitors of PTP1B and LMW-PTP, two protein tyrosine phosphatases (PTPs) which act as negative regulators of the metabolic and mitotic signalling of insulin. The synthesis of compounds 2 represents an example of utilizing phosphotyrosine-mimetics to identify effective low molecular weight nonphosphorus inhibitors of PTPs. several thiazolidinediones 2 exhibited PTP1 B inhibitory activity in the low micromolar range with moderate selectivity for human PTP1B and IF1 isoform of human LMW-PTP compared with other related PTPs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.027
• 作为产物：
  描述：

  对羟基苯甲醛 在 哌啶 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 4-[5-(4-Hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl]methylbenzoic acid
  参考文献：
  名称：

  5-Arylidene-4-Thiazolidinone Derivatives Active as Antidegenerative Agents on Human Chondrocyte Cultures

  摘要：

  5-芳基亚乙烯基-2-氧基-4-噻唑烷酮和2-苯基亚胺类似物被评估其在IL-1β刺激下的人类软骨细胞培养中的抗退化活性及其对基质金属蛋白酶-13的抑制能力。我们的结果表明，5-芳基亚乙烯基-4-噻唑烷酮衍生物1-9表现出抗退化活性，能够在骨关节炎过程中阻止多重软骨破坏。在选择的化合物中，(5-芳基-2,4-二氧噻唑烷-3-基)乙酸7-9在减少NO释放和恢复接受IL-1β处理的软骨细胞正常GAGs水平方面显示出显著效果。此外，苯甲酸1、5和6被证实为有效的MMP-13抑制剂，并能够恢复正常的GAGs水平。

  DOI：

  10.2174/157340613804488378

文献信息

• 5-Arylidene-4-Thiazolidinone Derivatives Active as Antidegenerative Agents on Human Chondrocyte Cultures
  作者：Annamaria Panico、Rosanna Maccari、Venera Cardile、Lucia Crasci、Simone Ronsisvalle、Rosaria Ottana

  DOI：10.2174/157340613804488378

  日期：2013.2.1

  5-Arylidene-2-oxo-4-thiazolidinones and 2-phenylimino analogues were evaluated for their antidegenerative activity on human chondrocyte cultures stimulated by IL-1β and for their inhibitory capability against matrix metalloproteinase- 13. Our results indicated that 5-arylidene-4-thiazolidinone derivatives 1-9 exhibit antidegenerative activity and could block multiple cartilage destruction during the osteoarthritic process. Out of the selected compounds, (5-arylidene- 2,4-dioxothiazolidin-3-yl)acetic acids 7-9 showed significant effectiveness in reducing NO release and restoring normal levels of GAGs in chondrocytes treated with IL-1β. Moreover, benzoic acids 1, 5 and 6 proved to be effective MMP-13 inhibitors and were able to restore normal levels of GAGs.

  5-芳基亚乙烯基-2-氧基-4-噻唑烷酮和2-苯基亚胺类似物被评估其在IL-1β刺激下的人类软骨细胞培养中的抗退化活性及其对基质金属蛋白酶-13的抑制能力。我们的结果表明，5-芳基亚乙烯基-4-噻唑烷酮衍生物1-9表现出抗退化活性，能够在骨关节炎过程中阻止多重软骨破坏。在选择的化合物中，(5-芳基-2,4-二氧噻唑烷-3-基)乙酸7-9在减少NO释放和恢复接受IL-1β处理的软骨细胞正常GAGs水平方面显示出显著效果。此外，苯甲酸1、5和6被证实为有效的MMP-13抑制剂，并能够恢复正常的GAGs水平。
• 5-Arylidene-2,4-thiazolidinediones as inhibitors of protein tyrosine phosphatases
  作者：Rosanna Maccari、Paolo Paoli、Rosaria Ottanà、Michela Jacomelli、Rosella Ciurleo、Giampaolo Manao、Theodora Steindl、Thierry Langer、Maria Gabriella Vigorita、Guido Camici

  DOI：10.1016/j.bmc.2007.05.027

  日期：2007.8

  4-(5-Arylidene-2,4-dioxothiszolidin-3-yl)methylbenzoic acids (2) were synthesized and evaluated in vitro as inhibitors of PTP1B and LMW-PTP, two protein tyrosine phosphatases (PTPs) which act as negative regulators of the metabolic and mitotic signalling of insulin. The synthesis of compounds 2 represents an example of utilizing phosphotyrosine-mimetics to identify effective low molecular weight nonphosphorus inhibitors of PTPs. several thiazolidinediones 2 exhibited PTP1 B inhibitory activity in the low micromolar range with moderate selectivity for human PTP1B and IF1 isoform of human LMW-PTP compared with other related PTPs. (c) 2007 Elsevier Ltd. All rights reserved.