(5Z)-5-(3-chloro-5-ethoxy-4-hydroxybenzylidene)-2-(4-chlorophenylimino)-3-methylthiazolidin-4-one | 1350612-59-7

• 英文名称: (5Z)-5-(3-chloro-5-ethoxy-4-hydroxybenzylidene)-2-(4-chlorophenylimino)-3-methylthiazolidin-4-one
• 英文别名: HL006
• CAS: 1350612-59-7
• 化学式: C₁₉H₁₆Cl₂N₂O₃S
• 分子量: 423.32
• InChiKey: MDHPVXFCAALTOM-FIMHLPJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  62.13
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  对氯苯胺 在 哌啶 、 sodium acetate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 27.0h， 生成 (5Z)-5-(3-chloro-5-ethoxy-4-hydroxybenzylidene)-2-(4-chlorophenylimino)-3-methylthiazolidin-4-one
  参考文献：
  名称：

  HL005—A new selective PPARγ antagonist specifically inhibits the proliferation of MCF-7

  摘要：

  Peroxisome proliferator-activated receptor-gamma (PPAR gamma) is a nuclear transcription factor which is involved in many diseases, such as diabetes, inflammation, dyslipidemia. hypertension, and cancer. Recently, there are many reports showing that PPAR gamma agonists have preclinical and clinical anticancer activity, with relatively few reports on anticancer effects of PPAR gamma antagonists. From our compound library, a novel 3-thiazolinone-modified benzoic acid derivative HL005 is found as PPAR gamma selective ligand through SPR analysis (K-D = 0.21 mu M), yeast two-hybrid results suggest that HL005 antagonize the potent PPAR gamma agonist rosiglitazone-induced recruitment of the coactivator for PPAR gamma (IC50 = 7.97 mu M). Different from the most reported PPAR gamma antagonist, HL005 can inhibit the proliferation of MCF-7 cell line in a concentration-dependent manner and induce cell cycle arrest at G2/M phase, other than interference with cell adhesion. In order to study the binding mode of this compound, three derivatives are synthesized to get more detail about the structure-activity relationship, molecular docking and the NMR spectra indicate that similar to most PPAR gamma ligand, the carboxylic acid group is an important moiety for HL005 and contributes strong interaction with PPAR gamma. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2011.01.019