6-[2-(benzoxazol-2-ylmethylamino)ethoxy]-1-benzyl-1H-indole-2-carboxylic acid methyl ester | 881795-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-[2-(benzoxazol-2-ylmethylamino)ethoxy]-1-benzyl-1H-indole-2-carboxylic acid methyl ester
• CAS: 881795-66-0
• 化学式: C₂₇H₂₅N₃O₄
• 分子量: 455.513
• InChiKey: SDEGROGKBURFEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  645.4±65.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.73
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-[2-(benzoxazol-2-ylmethylamino)ethoxy]-1-benzyl-1H-indole-2-carboxylic acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以69%的产率得到6-[2-(benzoxazol-2-yl-methyl-amino)-ethoxy]-1-benzyl-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of benzoxazole containing indole analogs as peroxisome proliferator-activated receptor-γ/δ dual agonists

  摘要：

  A series of benzoxazole or benzothiazole containing indole analogs, 6-alkoxyindole-2-carboxylic acids and 5-alkoxy-3-indolylacetic acids, were synthesized as novel candidates of PPAR gamma/delta dual agonists and their ligand activities for PPAR subtypes (alpha, gamma and delta) were investigated. In transient transactivation assay, several compounds activated PPAR gamma and delta with little activity of PPAR alpha. Putative binding mode of the compounds 1a and 2a in the active site of PPAR gamma was similar with that of rosiglitazone and the molecular modeling provides molecular insight to the observed activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.027
• 作为产物：
  描述：

  2-氯苯并恶唑 在 4-二甲氨基吡啶 、 sodium methylate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 9.83h， 生成 6-[2-(benzoxazol-2-ylmethylamino)ethoxy]-1-benzyl-1H-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of benzoxazole containing indole analogs as peroxisome proliferator-activated receptor-γ/δ dual agonists

  摘要：

  A series of benzoxazole or benzothiazole containing indole analogs, 6-alkoxyindole-2-carboxylic acids and 5-alkoxy-3-indolylacetic acids, were synthesized as novel candidates of PPAR gamma/delta dual agonists and their ligand activities for PPAR subtypes (alpha, gamma and delta) were investigated. In transient transactivation assay, several compounds activated PPAR gamma and delta with little activity of PPAR alpha. Putative binding mode of the compounds 1a and 2a in the active site of PPAR gamma was similar with that of rosiglitazone and the molecular modeling provides molecular insight to the observed activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.027