1-(4-Cyanophenyl)-3-(2-phenylethyl)urea | 886539-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-Cyanophenyl)-3-(2-phenylethyl)urea
• CAS: 886539-20-4
• 化学式: C₁₆H₁₅N₃O
• 分子量: 265.315
• InChiKey: RDHNTVURWOURON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-Cyanophenyl)-3-(2-phenylethyl)urea 在 盐酸羟胺 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 生成 N'-hydroxy-4-(3-phenethylureido)benzimidamide
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation of amidoximes as histone deacetylase inhibitors for cancer therapy

  摘要：

  Amindoximes are geometric isomers of N-hydroxyamidines which are bioisosteres of hydroxamates. Since amindoxime group is capable of chelating transition metal ions including zinc ion, amindoximes should possess histone deacetylases (HDACs) inhibitory activity. In this work, we designed and synthesized a series of amindoximes, examined their inhibitory activities against HDACs, and investigated their cytotoxicity to human cancer cells. Preliminary results demonstrated that amindoximes possessed submicromolar HDACs inhibitory activity, with noteworthy enhancement compared with hydroxamates. Furthermore, the amindoximes arrested HCT116 and A549 cells in G2/M phase and showed good efficacy in inducing cells death. We provided a proof-of-concept that amindoximes could be used as HDACs inhibitors and hold great promise as epigenetic drugs. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.08.073
• 作为产物：
  描述：

  对氨基苯腈 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 1-(4-Cyanophenyl)-3-(2-phenylethyl)urea
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation of amidoximes as histone deacetylase inhibitors for cancer therapy

  摘要：

  Amindoximes are geometric isomers of N-hydroxyamidines which are bioisosteres of hydroxamates. Since amindoxime group is capable of chelating transition metal ions including zinc ion, amindoximes should possess histone deacetylases (HDACs) inhibitory activity. In this work, we designed and synthesized a series of amindoximes, examined their inhibitory activities against HDACs, and investigated their cytotoxicity to human cancer cells. Preliminary results demonstrated that amindoximes possessed submicromolar HDACs inhibitory activity, with noteworthy enhancement compared with hydroxamates. Furthermore, the amindoximes arrested HCT116 and A549 cells in G2/M phase and showed good efficacy in inducing cells death. We provided a proof-of-concept that amindoximes could be used as HDACs inhibitors and hold great promise as epigenetic drugs. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.08.073

文献信息

• Arylalkyl Ureas As Cb1 Antagonists
  申请人：Hutchison J. Alan

  公开号：US20080009477A1

  公开（公告）日：2008-01-10

  CB1 antagonists are provided. Such compounds may be used to modulate CB1 activity in vivo or in vitro, and are particularly useful in the treatment of conditions responsive to CB1 receptor modulation in humans, domesticated companion animals and livestock animals, including appetite disorders, obesity and addictive disorders. Pharmaceutical compositions and methods for using them to treat such disorders are provided, as are methods for using ligands for receptor localization studies and various in vitro assays.

  提供CB1拮抗剂。这些化合物可以用于体内或体外调节CB1活性，并且在治疗人类、家养伴侣动物和家畜动物对CB1受体调节有反应的疾病，包括食欲失调、肥胖和成瘾性疾病方面特别有用。提供了用于治疗这些疾病的制药组合物和方法，以及用于受体定位研究和各种体外测定的配体使用方法。
• Design, synthesis and in vitro evaluation of amidoximes as histone deacetylase inhibitors for cancer therapy
  作者：Peifu Jiao、Peng Jin、Chencan Li、Lechao Cui、Lihua Dong、Bin Pan、Wentong Song、Liang Ma、Jinlong Dong、Lei Song、Xinjie Jin、Faming Li、Maosheng Wan、Zhitao Lv、Qiaohong Geng

  DOI：10.1016/j.bmcl.2016.08.073

  日期：2016.10

  Amindoximes are geometric isomers of N-hydroxyamidines which are bioisosteres of hydroxamates. Since amindoxime group is capable of chelating transition metal ions including zinc ion, amindoximes should possess histone deacetylases (HDACs) inhibitory activity. In this work, we designed and synthesized a series of amindoximes, examined their inhibitory activities against HDACs, and investigated their cytotoxicity to human cancer cells. Preliminary results demonstrated that amindoximes possessed submicromolar HDACs inhibitory activity, with noteworthy enhancement compared with hydroxamates. Furthermore, the amindoximes arrested HCT116 and A549 cells in G2/M phase and showed good efficacy in inducing cells death. We provided a proof-of-concept that amindoximes could be used as HDACs inhibitors and hold great promise as epigenetic drugs. (C) 2016 Elsevier Ltd. All rights reserved.