ethyl 2-(4-methoxy-3-((4-(trifluoromethyl)benzamido)methyl)benzyl)pentanoate | 915942-84-6

• 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: ethyl 2-(4-methoxy-3-((4-(trifluoromethyl)benzamido)methyl)benzyl)pentanoate
• CAS: 915942-84-6
• 化学式: C₂₄H₂₈F₃NO₄
• 分子量: 451.486
• InChiKey: GQWZPJKGQNWSOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-methoxy-3-((4-(trifluoromethyl)benzamido)methyl)benzyl)pentanoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-(4-methoxy-3-((4-(trifluoromethyl)benzamido)methyl)benzyl)pentanoic acid
  参考文献：
  名称：

  Design, synthesis, and evaluation of a novel series of α-substituted phenylpropanoic acid derivatives as human peroxisome proliferator-activated receptor (PPAR) α/δ dual agonists for the treatment of metabolic syndrome

  摘要：

  A series of alpha-alkyl-substituted phenylpropanoic acids was prepared as dual agonists of peroxisome proliferator-activated receptors alpha and delta (PPAR alpha/delta). Structure-activity relationship studies indicated that the shape of the linking group and the shape of the substituent at the distal benzene ring play key roles in determining the potency and the selectivity of PPAR subtype transactivation. Structure-activity relationships among the amide series (10) and the reversed amide series (13) are similar, but not identical, especially in the case of the compounds bearing a bulky hydrophobic substituent at the distal benzene ring, indicating that the hydrophobic tail part of the molecules in these two series binds at somewhat different positions in the large binding pocket of PPAR. alpha-Alkyl-substituted phenylpropanoic acids of (S)-configuration were identified as potent human PPAR alpha/delta dual agonists. Representative compounds exhibited marked nuclear receptor selectivity for PPAR alpha and PPAR delta. Subtype-selective PPAR activation was also examined by analysis of the mRNA expression of PPAR-regulated genes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.001
• 作为产物：
  描述：

  ethyl 2-[(3-formyl-4-methoxyphenyl)methyl]pentanoate 、 4-(三氟甲基)苯甲酰胺 在 三乙基硅烷 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 生成 ethyl 2-(4-methoxy-3-((4-(trifluoromethyl)benzamido)methyl)benzyl)pentanoate
  参考文献：
  名称：

  Design, synthesis, and evaluation of potent, structurally novel peroxisome proliferator-activated receptor (PPAR) δ-selective agonists

  摘要：

  A series of 3-(4-alkoxyphenyl)propanoic acid derivatives was prepared as candidate peroxisome proliferator-activated receptor (PPAR) 6-selective agonists, based on our previously discovered potent human PPAR alpha/delta dual agonist TIPP-401 as a lead compound. Structure-activity relationship studies clearly indicated the importance of the chain length of the alkoxy group at the 4-position, and the n-butoxy compound exhibited the most potent PPAR delta transactivation activity and highest PPAR delta selectivity. The (S)-enantiomer of a representative compound exhibited extremely potent PPAR delta transactivation activity, comparable with or somewhat superior to that of the known PPAR delta-selective agonist, GW-501516. The representative compound regulated the expression of genes involved in lipid and glucose homeostasis, and should be useful not only as a chemical tool to study PPAR delta function, but also as a candidate drug for the treatment of metabolic syndrome. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.023