melodamide A

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: melodamide A
• 英文别名: N-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethyl]-3-phenylprop-2-enamide
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: GBKHYRFDRRJFQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-hydroxyphenethyl)cinnamamide 在 碘苯二乙酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.0h， 以23%的产率得到melodamide A
  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

• 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.