(2E)-N-[3-(1H-imidazol-1-yl)propyl]-3-phenylprop-2-enamide

• 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: (2E)-N-[3-(1H-imidazol-1-yl)propyl]-3-phenylprop-2-enamide
• 英文别名: N-[3-(1H-Imidazol-1-yl)propyl]cinnamamide；n-[3-(1h-Imidazol-1-yl)propyl]-3-phenylacrylamide；(E)-N-(3-imidazol-1-ylpropyl)-3-phenylprop-2-enamide
• 化学式: C₁₅H₁₇N₃O
• 分子量: 255.319
• InChiKey: BMVJWBZHZVYRLB-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  肉桂酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (2E)-N-[3-(1H-imidazol-1-yl)propyl]-3-phenylprop-2-enamide
  参考文献：
  名称：

  Exploring the anti-biofilm activity of cinnamic acid derivatives in Candida albicans

  摘要：

  Some compounds, characterized by phenylethenyl moiety, such as methyl cinnamate and caffeic acid phenethyl ester, are able to inhibit C. albicans biofilm formation. On these bases, and as a consequence of our previous work, we synthesized a series of cinnamoyl ester and amide derivatives in order to evaluate them for the activity against C. albicans biofilm and planlctonically grown cells.The most active compounds 7 and 8 showed >> 50% biofilm inhibition concentrations (BMIC50) of 2 mu g/mL and 4 mu g/mL respectively, against C albicans biofilm formation; otherwise, 7 showed an interesting activity also against mature biofilm, with BMIC50 of 8 mu g/mL. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.091

文献信息

• N-[2-4-(1H-Imidazol-1-yl)alkyl]-arylamides and pharmaceutical
  申请人：American Cyanamid Company

  公开号：US04568687A1

  公开（公告）日：1986-02-04

  This disclosure describes novel N-[.omega.-(1H-imidazol-1-yl)alkyl]arylamides which possess the property of inhibiting the enzyme thromboxane synthetase and are also useful in the treatment of hypertension and myocardial ischemia.

  这份披露描述了一种新颖的N-[.omega.-(1H-咪唑-1-基)烷基]芳基酰胺，具有抑制血栓素合酶酶活性的特性，并且在治疗高血压和心肌缺血方面也很有用。
• N-(2-4-(1H-imidazol-1-yl)alkyl)arylamides
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0117462A2

  公开（公告）日：1984-09-05

  This disclosure describes novel N-[ω-(1H-imidazol-1-yl)alkyl]arylamides which possess the property of inhibiting the enzyme thromboxane synthetase and are also useful in the treatment of hypertension and myocardial ischemia.

  本公开介绍了新型 N-[ω-(1H-咪唑-1-基)烷基]芳基酰胺，它们具有抑制血栓素合成酶的特性，还可用于治疗高血压和心肌缺血。
• US4568687A
  申请人：——

  公开号：US4568687A

  公开（公告）日：1986-02-04
• Exploring the anti-biofilm activity of cinnamic acid derivatives in Candida albicans
  作者：Daniela De Vita、Giovanna Simonetti、Fabiana Pandolfi、Roberta Costi、Roberto Di Santo、Felicia Diodata D’Auria、Luigi Scipione

  DOI：10.1016/j.bmcl.2016.10.091

  日期：2016.12

  Some compounds, characterized by phenylethenyl moiety, such as methyl cinnamate and caffeic acid phenethyl ester, are able to inhibit C. albicans biofilm formation. On these bases, and as a consequence of our previous work, we synthesized a series of cinnamoyl ester and amide derivatives in order to evaluate them for the activity against C. albicans biofilm and planlctonically grown cells.The most active compounds 7 and 8 showed >> 50% biofilm inhibition concentrations (BMIC50) of 2 mu g/mL and 4 mu g/mL respectively, against C albicans biofilm formation; otherwise, 7 showed an interesting activity also against mature biofilm, with BMIC50 of 8 mu g/mL. (C) 2016 Elsevier Ltd. All rights reserved.