2,2-bis(ethoxycarbonyl)-2-(3-methoxyphenyl)propionic acid | 339309-52-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2,2-bis(ethoxycarbonyl)-2-(3-methoxyphenyl)propionic acid
• CAS: 339309-52-3
• 化学式: C₁₆H₂₀O₇
• 分子量: 324.331
• InChiKey: OXJDANIJWOUTCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  99.13
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,2-bis(ethoxycarbonyl)-2-(3-methoxyphenyl)propionic acid 在 bis-triphenylphosphine-palladium(II) chloride 、 草酰氯 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 22.5h， 生成 cis-methyl 6-hydroxy-3-(2-thienyl)-1-indancarboxylate
  参考文献：
  名称：

  Design, syntheses, and structure–Activity relationships of indan derivatives as endothelin antagonists; new lead generation of non-peptidic antagonist from peptidic leads

  摘要：

  A new lead generation of non-peptidic ETA antagonists from two peptidic ETA-selective ones. BQ-123 and FR139317, was performed. Using computer assisted molecular modeling, a putative pharmacophore was constructed from the superposition of the reported three-dimensional structure of the cyclic peptide BQ-123 and a presumable beta -turn active conformation of the linear peptide FR139317 formed by an intramolecular hydrogen bond. According to this model, a new series of indan derivatives were designed and synthesized. Among these, 5-isobutyrylamino-6-(1-naphthylmethyloxy)-3-(2-thienyl)-3-indancarboxylic acid (1b) showed a moderate ETA antagonistic activity (IC50=28 muM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00241-8
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以82%的产率得到2,2-bis(ethoxycarbonyl)-2-(3-methoxyphenyl)propionic acid
  参考文献：
  名称：

  Design, syntheses, and structure–Activity relationships of indan derivatives as endothelin antagonists; new lead generation of non-peptidic antagonist from peptidic leads

  摘要：

  A new lead generation of non-peptidic ETA antagonists from two peptidic ETA-selective ones. BQ-123 and FR139317, was performed. Using computer assisted molecular modeling, a putative pharmacophore was constructed from the superposition of the reported three-dimensional structure of the cyclic peptide BQ-123 and a presumable beta -turn active conformation of the linear peptide FR139317 formed by an intramolecular hydrogen bond. According to this model, a new series of indan derivatives were designed and synthesized. Among these, 5-isobutyrylamino-6-(1-naphthylmethyloxy)-3-(2-thienyl)-3-indancarboxylic acid (1b) showed a moderate ETA antagonistic activity (IC50=28 muM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00241-8