N-(4-cyanophenyl)-4-bromobutanamide | 167833-92-3

• 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: N-(4-cyanophenyl)-4-bromobutanamide
• 英文别名: 4-bromo-N-(4-cyanophenyl)butanamide
• CAS: 167833-92-3
• 化学式: C₁₁H₁₁BrN₂O
• 分子量: 267.125
• InChiKey: ODUGPDFREXXYNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-cyanophenyl)-4-bromobutanamide 在 叠氮基三甲基硅烷 、 二正丁基氧化锡 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 4-(4-acetyl-3-hydroxy-2-propylphenoxy)-N-[4-(2H-tetrazol-5-yl)phenyl]butanamide
  参考文献：
  名称：

  Allosteric potentiators of the metabotropic glutamate receptor 2 (mGlu2). Part 1: Identification and synthesis of phenyl-tetrazolyl acetophenones

  摘要：

  We have identified and synthesized a series of aryl-tetrazoyl acetophenones as positive allosteric potentiators of the metabotropic glutamate receptor 2. Structure activity relationship studies directed toward improving the potency and level of potentiation led to the discovery of 22 (EC50 = 93 nM, 128% potentiation). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.020
• 作为产物：
  描述：

  4-溴丁酰氯 、 对氨基苯腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以27.7 g (96%)的产率得到N-(4-cyanophenyl)-4-bromobutanamide
  参考文献：
  名称：

  Platelet aggregation inhibitors

  摘要：

  这项发明涉及具有以下结构式的化合物##STR1##或其药用可接受盐，这些化合物对抑制血小板聚集具有用处，以及这些苯基酰胺衍生物的药物组合物，以及通过给予这些化合物和组合物来抑制哺乳动物的血小板聚集的方法。

  公开号：

  US05721366A1

文献信息

• 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.
• 1-AMIDINOPHENYL-PYRROLIDONES PIPERIDINONES AZETINONES AS PLATELET AGGREGATION INHIBITORS
  申请人：G.D. SEARLE & CO.

  公开号：EP0691953A1

  公开（公告）日：1996-01-17
• 1-AMIDINOPHENYL-PYRROLIDONES/ PIPERIDINONES AS PLATELET AGGREGATION INHIBITORS
  申请人：G.D. SEARLE & CO.

  公开号：EP0691953B1

  公开（公告）日：2000-08-02
• US5721366A
  申请人：——

  公开号：US5721366A

  公开（公告）日：1998-02-24
• US5986107A
  申请人：——

  公开号：US5986107A

  公开（公告）日：1999-11-16