3-(3-(2-methoxyphenyl)-4-oxo-2-thiazolidinyl)benzoic acid | 1395435-10-5

• 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: 3-(3-(2-methoxyphenyl)-4-oxo-2-thiazolidinyl)benzoic acid
• 英文别名: 3-(3-(2-Methoxyphenyl)-4-oxothiazolidin-2-yl)benzoic acid；3-[3-(2-methoxyphenyl)-4-oxo-1,3-thiazolidin-2-yl]benzoic acid
• CAS: 1395435-10-5
• 化学式: C₁₇H₁₅NO₄S
• 分子量: 329.376
• InChiKey: IXSXEIPCIXQHQN-UHFFFAOYSA-N

物化性质

• 沸点：
  639.7±55.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3-(2-methoxyphenyl)-4-oxo-2-thiazolidinyl)benzoic acid 在 盐酸羟胺 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 N-(3-(hydroxycarbamoyl)propyl)-3-(3-(2-methoxyphenyl)-4-oxo-2-thiazolidinyl)benzamide
  参考文献：
  名称：

  A hybrid of thiazolidinone with the hydroxamate scaffold for developing novel histone deacetylase inhibitors with antitumor activities

  摘要：

  一系列新型组蛋白去乙酰化酶（HDAC）抑制剂基于将经典HDAC抑制剂的药效团与噻唑烷酮骨架混合的策略进行设计、合成和评估。

  DOI：

  10.1039/c5ob02250a
• 作为产物：
  描述：

  3-甲醛苯甲酸甲酯 在 lithium hydroxide monohydrate 、 水 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 3-(3-(2-methoxyphenyl)-4-oxo-2-thiazolidinyl)benzoic acid
  参考文献：
  名称：

  Optimization of 2-(3-(arylalkyl amino carbonyl) phenyl)-3-(2-methoxyphenyl)-4-thiazolidinone derivatives as potent antitumor growth and metastasis agents

  摘要：

  A series of 2,3-diaryl-4-thiazolidinone derivatives were synthesized and evaluated for their antiproliferative properties against two well-known cancer cell lines (A549 as human lung cancer and MDA-MB-231 as human breast cancer). Structure activity relationship (SAR) analysis resulted in the discovery of 2-(3-(arylalkyl amino carbonyl)phenyl)-3-(2-methoxy-phenyl)-4-thiazolidinone derivatives with high potent inhibitory effects on the proliferation of both cancer cell lines. Furthermore, several compounds with potent antiproliferative activities displayed excellent inhibitory activities on migration with an IC50 of about 0.05 μM on MDA-MB-231 cells in two different migration assays. In particular, compound 39 was indicated to suppress tumor growth and metastasis as well as promote survival rate. Intriguingly, this series of analogs have been indicated to inhibit tumor cell proliferation through inducing cell cycle arrest. These results suggested that the new series of 2-(3-(arylalkyl amino carbonyl)phenyl)-3-(2-methoxyphenyl)-4-thiazolidinone derivatives could be regarded and developed as novel highly potential anticancer agents in the future.

  DOI：

  10.1016/j.ejmech.2014.04.068

文献信息

• A hybrid of thiazolidinone with the hydroxamate scaffold for developing novel histone deacetylase inhibitors with antitumor activities
  作者：Feifei Yang、Shihong Peng、Yunqi Li、Liqiang Su、Yangrui Peng、Jing Wu、Huang Chen、Mingyao Liu、Zhengfang Yi、Yihua Chen

  DOI：10.1039/c5ob02250a

  日期：——

  A series of novel histone deacetylase (HDAC) inhibitors were designed, synthesized and evaluated based on the strategies of a hybrid of the classic pharmacophore of HDAC inhibitors with the thiazolidinone scaffold.

  一系列新型组蛋白去乙酰化酶（HDAC）抑制剂基于将经典HDAC抑制剂的药效团与噻唑烷酮骨架混合的策略进行设计、合成和评估。
• Optimization of 2-(3-(arylalkyl amino carbonyl) phenyl)-3-(2-methoxyphenyl)-4-thiazolidinone derivatives as potent antitumor growth and metastasis agents
  作者：Jing Wu、Linxi Yu、Feifei Yang、Jingjie Li、Peng Wang、Wenbo Zhou、Liwen Qin、Yunqi Li、Jian Luo、Zhengfang Yi、Mingyao Liu、Yihua Chen

  DOI：10.1016/j.ejmech.2014.04.068

  日期：2014.6

  A series of 2,3-diaryl-4-thiazolidinone derivatives were synthesized and evaluated for their antiproliferative properties against two well-known cancer cell lines (A549 as human lung cancer and MDA-MB-231 as human breast cancer). Structure activity relationship (SAR) analysis resulted in the discovery of 2-(3-(arylalkyl amino carbonyl)phenyl)-3-(2-methoxy-phenyl)-4-thiazolidinone derivatives with high potent inhibitory effects on the proliferation of both cancer cell lines. Furthermore, several compounds with potent antiproliferative activities displayed excellent inhibitory activities on migration with an IC50 of about 0.05 μM on MDA-MB-231 cells in two different migration assays. In particular, compound 39 was indicated to suppress tumor growth and metastasis as well as promote survival rate. Intriguingly, this series of analogs have been indicated to inhibit tumor cell proliferation through inducing cell cycle arrest. These results suggested that the new series of 2-(3-(arylalkyl amino carbonyl)phenyl)-3-(2-methoxyphenyl)-4-thiazolidinone derivatives could be regarded and developed as novel highly potential anticancer agents in the future.