{5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-methoxycarbonylmethyl-1H-indol-3-yl}acetic acid methyl ester | 1275597-93-7

• 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: {5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-methoxycarbonylmethyl-1H-indol-3-yl}acetic acid methyl ester
• 英文别名: Methyl 2-[5-[3-[1,3-benzoxazol-2-yl(methyl)amino]propoxy]-1-(2-methoxy-2-oxoethyl)indol-3-yl]acetate
• CAS: 1275597-93-7
• 化学式: C₂₅H₂₇N₃O₆
• 分子量: 465.506
• InChiKey: FFTABZKZNARKQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  624.0±65.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-methoxycarbonylmethyl-1H-indol-3-yl}acetic acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以54%的产率得到{5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-methoxycarbonylmethyl-1H-indol-3-yl}acetic 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 、 三丁基膦 、 caesium carbonate 、 三乙胺 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 {5-[3-(benzooxazol-2-ylmethylamino)propoxy]-1-methoxycarbonylmethyl-1H-indol-3-yl}acetic 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

文献信息

• Design and synthesis of benzoxazole containing indole analogs as peroxisome proliferator-activated receptor-γ/δ dual agonists
  作者：Hyo Jin Gim、Ye-Jin Cheon、Jae-Ha Ryu、Raok Jeon

  DOI：10.1016/j.bmcl.2011.03.027

  日期：2011.5

  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.