2-[1-Benzyl-6-(3-phenoxazin-10-ylpropoxy)indol-3-yl]acetic acid | 1418140-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-[1-Benzyl-6-(3-phenoxazin-10-ylpropoxy)indol-3-yl]acetic acid
• 英文别名: 2-[1-benzyl-6-(3-phenoxazin-10-ylpropoxy)indol-3-yl]acetic acid
• CAS: 1418140-89-2
• 化学式: C₃₂H₂₈N₂O₄
• 分子量: 504.585
• InChiKey: SPNIJWZKZYPYTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 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 、 水 、 氢气 、 三正丁基氢锡 、 palladium diacetate 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 三对苯甲基膦 、 sodium hydroxide 、 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 、 mineral oil 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 28.5h， 生成 2-[1-Benzyl-6-(3-phenoxazin-10-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

文献信息

• Design and synthesis of alkoxyindolyl-3-acetic acid analogs as peroxisome proliferator-activated receptor-γ/δ agonists
  作者：Hyo Jin Gim、Hua Li、Eun Lee、Jae-Ha Ryu、Raok Jeon

  DOI：10.1016/j.bmcl.2012.11.033

  日期：2013.1

  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.