[6-(3-carbazol-9-yl-propoxy)-1H-indol-3-yl]acetic acid methyl ester | 1418140-80-3

• 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-(3-carbazol-9-yl-propoxy)-1H-indol-3-yl]acetic acid methyl ester
• 英文别名: methyl 2-[6-(3-carbazol-9-ylpropoxy)-1H-indol-3-yl]acetate
• CAS: 1418140-80-3
• 化学式: C₂₆H₂₄N₂O₃
• 分子量: 412.488
• InChiKey: JETFZERWUNIBEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [6-(3-carbazol-9-yl-propoxy)-1H-indol-3-yl]acetic acid methyl ester 在 水 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 14.0h， 生成 2-[1-Benzyl-6-(3-carbazol-9-ylpropoxy)indol-3-yl]acetic acid
  参考文献：
  名称：

  Design and synthesis of alkoxyindolyl-3-acetic acid analogs as peroxisome proliferator-activated receptor-γ/δ agonists

  摘要：

  A series of carbazole or phenoxazine containing alkoxyindole-3-acetic acid analogs were prepared as PPAR gamma/delta agonists and their transactivation activities for PPAR receptor subtypes (alpha, gamma and delta) were investigated. Structure-activity relationship studies disclosed the effect of the lipophilic tail, attaching position of the alkoxy group and N-benzyl substitution at indole. Compound 1b was the most potent for PPARd and 3b for PPAR gamma. Molecular modeling suggested two different binding modes of our alkoxyindole-3-acetic acid analogs providing the insight into their PPAR activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.033
• 作为产物：
  描述：

  4-碘-3-硝基苯酚 在 吡啶 、 偶氮二异丁腈 、 三丁基膦 、 三光气 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 三正丁基氢锡 、 palladium diacetate 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 三对苯甲基膦 、 锌 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 丙酮 、 甲苯 、 乙腈 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 14.5h， 生成 [6-(3-carbazol-9-yl-propoxy)-1H-indol-3-yl]acetic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of alkoxyindolyl-3-acetic acid analogs as peroxisome proliferator-activated receptor-γ/δ agonists

  摘要：

  A series of carbazole or phenoxazine containing alkoxyindole-3-acetic acid analogs were prepared as PPAR gamma/delta agonists and their transactivation activities for PPAR receptor subtypes (alpha, gamma and delta) were investigated. Structure-activity relationship studies disclosed the effect of the lipophilic tail, attaching position of the alkoxy group and N-benzyl substitution at indole. Compound 1b was the most potent for PPARd and 3b for PPAR gamma. Molecular modeling suggested two different binding modes of our alkoxyindole-3-acetic acid analogs providing the insight into their PPAR activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.033