3-(1,3-benzodioxol-5-yl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide | 155174-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-(1,3-benzodioxol-5-yl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
• CAS: 155174-38-2
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: GWVOWTGEVSYSEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1,3-benzodioxol-5-yl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide 在 碘苯二乙酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Isolation and Synthesis of Melodamide A, a New Anti-inflammatory Phenolic Amide from the Leaves of Melodorum fruticosum

  摘要：

  Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 mu M. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.

  DOI：

  10.1055/s-0032-1328131
• 作为产物：
  描述：

  对羟基苯乙胺 、 3-benzo[1,3]dioxol-5-yl-acryloyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-(1,3-benzodioxol-5-yl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
  参考文献：
  名称：

  Isolation and Synthesis of Melodamide A, a New Anti-inflammatory Phenolic Amide from the Leaves of Melodorum fruticosum

  摘要：

  Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 mu M. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.

  DOI：

  10.1055/s-0032-1328131

文献信息

• 一种抗炎化合物及其制备方法和用途
  申请人：中国人民解放军空军军医大学

  公开号：CN115417788A

  公开（公告）日：2022-12-02

  本发明公开了一种抗炎化合物及其制备方法和用途，该抗炎化合物是以天然产物HOEC、其类似物HOEAC为基本骨架，经对其衍生物的设计、合成形成的药物活性成分。所述抗炎化合物的结构如下所示，其作为抗炎分子对LPS诱导的炎症反应具有显著的抑制作用，可开发为对IBD具有治疗作用的抗炎药物。
• Isolation and Synthesis of Melodamide A, a New Anti-inflammatory Phenolic Amide from the Leaves of Melodorum fruticosum
  作者：Hsiu-Hui Chan、Tsong-Long Hwang、Tran Thang、Yann-Lii Leu、Ping-Chung Kuo、Bui Nguyet、Do Dai、Tian-Shung Wu

  DOI：10.1055/s-0032-1328131

  日期：——

  Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 mu M. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.