(E)-(9H-carbazol-3-yl)-3-(4-methoxyphenyl)acrylamide

• 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: (E)-(9H-carbazol-3-yl)-3-(4-methoxyphenyl)acrylamide
• 英文别名: (E)-N-(9H-carbazol-3-yl)-3-(4-methoxyphenyl)prop-2-enamide
• 化学式: C₂₂H₁₈N₂O₂
• 分子量: 342.397
• InChiKey: PQODPCGGKQYCHB-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-硝基-9h-咔唑 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、172.37 kPa 条件下， 反应 27.0h， 生成 (E)-(9H-carbazol-3-yl)-3-(4-methoxyphenyl)acrylamide
  参考文献：
  名称：

  Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives

  摘要：

  In this Letter, we investigated the barrier protective effects of 3-N-(MeO)(n)-cinnamoyl carbazoles (BS 1; n = 1, BS 2; n = 2, BS 3; n = 3) and 3-O-(MeO)(3)-cinnamoyl carbazole (BS 4) against high-mobility group box 1 (HMGB1)-mediated vascular disruptive responses in human umbilical vein endothelial cells (HUVECs) and in mice for the first time. Data showed that BS 2, BS 3, and BS 4, but not BS 1, inhibited HMGB1-mediated vascular disruptive responses and transendothelial migration of human neutrophils to HUVECs. BS 2, BS3, and BS 4 also suppressed HMGB1-induced hyperpermeability and leukocyte migration in mice. Interestingly, the barrier protective effects of BS 3 and BS 4 were better than those of BS 2. These results suggest that the number of methoxy groups substituted on the cinnamamide or cinnamate moiety of the 9H-3-carbazole derivative is an important pharmacophore for the barrier protective effects of these compounds. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.079

文献信息

• Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives
  作者：Sae-Kwang Ku、Jee-Hyun Lee、Yuseok O、Wonhwa Lee、Gyu-Yong Song、Jong-Sup Bae

  DOI：10.1016/j.bmcl.2015.07.079

  日期：2015.10

  In this Letter, we investigated the barrier protective effects of 3-N-(MeO)(n)-cinnamoyl carbazoles (BS 1; n = 1, BS 2; n = 2, BS 3; n = 3) and 3-O-(MeO)(3)-cinnamoyl carbazole (BS 4) against high-mobility group box 1 (HMGB1)-mediated vascular disruptive responses in human umbilical vein endothelial cells (HUVECs) and in mice for the first time. Data showed that BS 2, BS 3, and BS 4, but not BS 1, inhibited HMGB1-mediated vascular disruptive responses and transendothelial migration of human neutrophils to HUVECs. BS 2, BS3, and BS 4 also suppressed HMGB1-induced hyperpermeability and leukocyte migration in mice. Interestingly, the barrier protective effects of BS 3 and BS 4 were better than those of BS 2. These results suggest that the number of methoxy groups substituted on the cinnamamide or cinnamate moiety of the 9H-3-carbazole derivative is an important pharmacophore for the barrier protective effects of these compounds. (C) 2015 Elsevier Ltd. All rights reserved.