cinnamyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

• 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: cinnamyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
• 英文别名: [(E)-3-phenylprop-2-enyl] 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate
• 化学式: C₂₈H₂₄ClNO₄
• 分子量: 473.956
• InChiKey: LYLQYJYCLOSVOA-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cinnamyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate 、 tert-butyl 3-benzoylazetidine-1-carboxylate 在 4-苯基吡啶 、 双联(2,4-二甲基-2,4-戊二醇)硼酸酯 作用下， 以75 %的产率得到tert-butyl 3-benzoyl-5-((2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetoxy)methyl)-4-phenylpiperidine-1-carboxylate
  参考文献：
  名称：

  硼基自由基催化 (4+2) 环加成反应区域选择性和非对映选择性合成多取代哌啶

  摘要：

  硼基自由基催化的氮杂环丁烷与烯烃的分子间 (4+2) 环加成反应已被开发用于有效合成 3,4,5-多取代哌啶，其含有医学相关的关键杂环基序，并且不易通过其他方法获得。该反应具有模块化程度高、原子经济、操作简单、非金属催化剂廉价、底物范围广泛等特点。

  DOI：

  10.1002/anie.202406612
• 作为产物：
  描述：

  吲哚美辛 、 3-苯基丙-2-烯-1-醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 4.0h， 以60%的产率得到cinnamyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
  参考文献：
  名称：

  Esters of some non-steroidal anti-inflammatory drugs with cinnamyl alcohol are potent lipoxygenase inhibitors with enhanced anti-inflammatory activity

  摘要：

  Novel esters of non steroidal anti-inflammatory drugs, a-lipoic acid and indol-3-acetic acid with cinnamyl alcohol were synthesised by a straightforward method and at high yields (60-98%). They reduced acute inflammation more than the parent acids and are potent inhibitors of soybean lipoxygenase. Selected structures decreased plasma lipidemic indices in Triton-induced hyperlipidemia to rats. Therefore, the synthesised compounds may add to the current knowledge about agents acting against various inflammatory disorders. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.036

文献信息

• Esters of some non-steroidal anti-inflammatory drugs with cinnamyl alcohol are potent lipoxygenase inhibitors with enhanced anti-inflammatory activity
  作者：Panagiotis Theodosis-Nobelos、Malamati Kourti、Paraskevi Tziona、Panos N. Kourounakis、Eleni A. Rekka

  DOI：10.1016/j.bmcl.2015.10.036

  日期：2015.11

  Novel esters of non steroidal anti-inflammatory drugs, a-lipoic acid and indol-3-acetic acid with cinnamyl alcohol were synthesised by a straightforward method and at high yields (60-98%). They reduced acute inflammation more than the parent acids and are potent inhibitors of soybean lipoxygenase. Selected structures decreased plasma lipidemic indices in Triton-induced hyperlipidemia to rats. Therefore, the synthesised compounds may add to the current knowledge about agents acting against various inflammatory disorders. (C) 2015 Elsevier Ltd. All rights reserved.