4-methyl-2-(4-nitro-phenyl)-thiazole-5-carbonyl chloride | 16059-29-3

• 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-methyl-2-(4-nitro-phenyl)-thiazole-5-carbonyl chloride
• 英文别名: 4-Methyl-2-(4-nitrophenyl)-1,3-thiazole-5-carbonyl chloride；4-methyl-2-(4-nitrophenyl)-1,3-thiazole-5-carbonyl chloride
• CAS: 16059-29-3
• 化学式: C₁₁H₇ClN₂O₃S
• 分子量: 282.707
• InChiKey: UDDBMJANRJOZJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(4-nitro-phenyl)-thiazole-5-carbonyl chloride 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-methyl-2-[4-{[(4-methyl-2-[4-nitrophenyl]-thiazol-5-ylcarbonyl)amino]methyl}phenoxy]propionic acid
  参考文献：
  名称：

  Substituted 2-[(4-Aminomethyl)phenoxy]-2-methylpropionic Acid PPARα Agonists. 1. Discovery of a Novel Series of Potent HDLc Raising Agents

  摘要：

  The peroxisome proliferator activated receptors PPAR alpha, PPAR gamma, and PPAR delta are ligand-activated transcription factors that play a key role in lipid homeostasis. The fibrates raise circulating levels of high-density lipoprotein cholesterol and lower levels of triglycerides in part through their activity as PPAR alpha agonists; however, the low potency and restricted selectivity of the fibrates may limit their efficacy, and it would be desirable to develop more potent and selective PPAR alpha agonists. Modification of the selective PPAR delta agonist 1 (GW501516) so as to incorporate the 2-aryl-2-methylpropionic acid group of the fibrates led to a marked shift in potency and selectivity toward PPAR alpha agonism. Optimization of the series gave 25a, which shows EC50 = 4 nM on PPAR alpha and at least 500-fold selectivity versus PPAR delta and PPAR gamma. Compound 25a (GW590735) has been progressed to clinical trials for the treatment of diseases of lipid imbalance.

  DOI：

  10.1021/jm058056x
• 作为产物：
  描述：

  4-甲基-2-苯基-1,3-噻唑-5-甲酸乙酯 在 氢氧化钾 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 生成 4-methyl-2-(4-nitro-phenyl)-thiazole-5-carbonyl chloride
  参考文献：
  名称：

  Csavassy,G.; Gyoerfi,Z.A., Justus Liebigs Annalen der Chemie, 1974, p. 1195 - 1205

  摘要：

  DOI：