2-(2-methyl-5-nitroimidazol-1-yl)ethyl cinnamate

• 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: 2-(2-methyl-5-nitroimidazol-1-yl)ethyl cinnamate
• 英文别名: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl (2E)-3-phenylprop-2-enoate；(E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl cinnamate；(E)-2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethylcinnamate；2-(2-methyl-5-nitroimidazol-1-yl)ethyl (E)-3-phenylprop-2-enoate
• 化学式: C₁₅H₁₅N₃O₄
• 分子量: 301.302
• InChiKey: RHVQGNOZEPBSSD-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 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：
  89.9
• 氢给体数：
  0
• 氢受体数：
  5

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 2-(2-methyl-5-nitroimidazol-1-yl)ethyl cinnamate
  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

• Synthesis, molecular modeling, and biological evaluation of cinnamic acid metronidazole ester derivatives as novel anticancer agents
  作者：Yong Qian、Hong-Jia Zhang、Hao Zhang、Chen Xu、Jing Zhao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2010.06.003

  日期：2010.7

  A series of novel cinnamic acid metronidazole ester derivatives have been designed and synthesized, and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Compound 3h showed the most potent biological activity (IC50 = 0.62 μM for EGFR and IC50 = 2.15 μM for HER-2). Docking simulation was performed to position compound 3h into the EGFR active site to determine

  已经设计和合成了一系列新颖的肉桂酸甲硝唑酯衍生物，并且还评估了它们的生物活性作为潜在的EGFR和HER-2激酶抑制剂。化合物3H显示了最有效的生物活性（IC 50  = 0.62μM对EGFR和IC 50  = 2.15μM为HER-2）。进行对接模拟以将化合物3h置于EGFR活性位点，以确定可能的结合模型。抗增殖试验结果表明，这些化合物中的某些对MCF-7具有良好的抗增殖活性。在肿瘤生长抑制中具有有效抑制活性的化合物3h可能是潜在的抗癌药。
• OLIGOMER-NITROIMIDAZOLE ANTI-INFECTIVE CONJUGATES
  申请人：NEKTAR THERAPEUTICS

  公开号：US20140378520A1

  公开（公告）日：2014-12-25

  The invention provides (among other things) small molecule drugs that are chemically modified by covalent attachment of a water-soluble oligomer.

  本发明提供（除其他外）通过共价连接水溶性寡聚体进行化学修饰的小分子药物。
• Oligomer-Nitroimidazole Anti-Infective Conjugates
  申请人：Ren Zhongxu

  公开号：US20100317707A1

  公开（公告）日：2010-12-16

  The invention provides (among other things) small molecule drugs that are chemically modified by covalent attachment of a water soluble oligomer.

  本发明提供了（除其他外）通过共价连接水溶性寡聚体对化学修饰的小分子药物。
• Kapoor; Dubey; Mahindroo, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 1, p. 27 - 30
  作者：Kapoor、Dubey、Mahindroo

  DOI：——

  日期：——
• US8853247B2
  申请人：——

  公开号：US8853247B2

  公开（公告）日：2014-10-07