cinnamyl 2-(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-(1H-indol-3-yl)acetate
• 英文别名: [(E)-3-phenylprop-2-enyl] 2-(1H-indol-3-yl)acetate
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: KZTKNDJVKFBRLC-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-吲哚乙酸 、 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82%的产率得到cinnamyl 2-(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

• C‐H Functionalization of Heterocycles with Triplet Carbenes by means of an Unexpected 1,2‐Alkyl Radical Migration
  作者：Claire Empel、Sripati Jana、Łukasz Ciszewski、Katarzyna Zawada、Chao Pei、Dorota Gryko、Rene M. Koenigs

  DOI：10.1002/chem.202300214

  日期：——

  A triplet carbene is involved in the C3-H functionalization of indole heterocycles. We herein describe a combined experimental and computational study on this reaction and unveil an unexpected 1,2-alkyl radical migration pathway.

  三线态卡宾参与吲哚杂环的 C3-H 官能化。我们在此描述了对该反应的综合实验和计算研究，并揭示了一种意想不到的 1,2-烷基自由基迁移途径。
• 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.