2-(4-Chlorophenyl)imino-3-methyl-1,3-thiazolidin-4-one | 174212-69-2

• 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: 2-(4-Chlorophenyl)imino-3-methyl-1,3-thiazolidin-4-one
• CAS: 174212-69-2
• 化学式: C₁₀H₉ClN₂OS
• 分子量: 240.713
• InChiKey: LELKGRZPMDCDAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Chlorophenyl)imino-3-methyl-1,3-thiazolidin-4-one 、 3-氯-5-乙氧基-4-羟基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 15.0h， 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
• 作为产物：
  描述：

  1-(4-氯苯基)-3-甲基硫脲 、 氯乙酸 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 2-(4-Chlorophenyl)imino-3-methyl-1,3-thiazolidin-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

文献信息

• [EN] UBIQUITINATION MODULATORS<br/>[FR] MODULATEURS D'UBIQUITINATION
  申请人：ITI SCOTLAND LTD

  公开号：WO2011135303A2

  公开（公告）日：2011-11-03

  The use of compounds or pharmaceutically acceptable derivatives thereof which are ubiquitin modulators, in methods of treating cancer, inflammatory diseases, neurodegenerative diseases and/or cardiovascular diseases is described.
• HL005—A new selective PPARγ antagonist specifically inhibits the proliferation of MCF-7
  作者：Weiqiang Lu、Peng Che、Yanyan Zhang、Honglin Li、Shien Zou、Jin Zhu、Jing Deng、Xu Shen、Hualiang Jiang、Jian Li、Jin Huang

  DOI：10.1016/j.jsbmb.2011.01.019

  日期：2011.4

  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.