ethyl 2-[(3-formyl-4-methoxyphenyl)methyl]pentanoate | 943543-87-1

• 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-[(3-formyl-4-methoxyphenyl)methyl]pentanoate
• CAS: 943543-87-1
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: DBHFLIJNKWARTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(3-formyl-4-methoxyphenyl)methyl]pentanoate 、 4-(1-adamantyl)benzamide 在 三乙基硅烷 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以70%的产率得到
  参考文献：
  名称：

  SAR-oriented discovery of peroxisome proliferator-activated receptor pan agonist with a 4-adamantylphenyl group as a hydrophobic tail

  摘要：

  3-(4-Alkoxyphenyl)propanoic acid derivatives were prepared as candidate peroxisome proliferator-activated receptor (PPAR) alpha/delta/gamma pan agonists, based on our previous SAR studies directed toward the development of subtype-selective PPAR agonists. Those studies indicated that the steric bulkiness of substituents introduced at the distal benzene ring had an important influence on PPAR activity. The finding that a 4-adamantyl derivative exhibited not only PPAR alpha/delta activity but also significant PPAR gamma activity prompted us to search for structurally novel phenylpropanoic acid derivatives with more potent adipocyte differentiation activity than the well-known PPAR-gamma agonist, rosiglitazone, as well as well-balanced PPAR alpha and PPAR delta agonistic activities. A representative phenylpropanoic acid derivative (12) bearing a 4-adamantylphenyl substituent proved to be a well-balanced PPAR-pan agonist with activities to regulate the expression of genes involved in lipid and glucose homeostasis, and should be useful as a candidate drug for the treatment of altered PPAR function. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.001
• 作为产物：
  描述：

  ethyl 2-[(4-methoxyphenyl)methyl]pentanoate 、 1,1-二氯甲醚 在 四氯化钛 、 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 2-[(3-formyl-4-methoxyphenyl)methyl]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