(E)-N-(5-bromopentyl)-3-(3,4-dichlorophenyl)acrylamide | 603152-34-7

• 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: (E)-N-(5-bromopentyl)-3-(3,4-dichlorophenyl)acrylamide
• 英文别名: (E)-N-(5-bromopentyl)-3-(3,4-dichlorophenyl)prop-2-enamide
• CAS: 603152-34-7
• 化学式: C₁₄H₁₆BrCl₂NO
• 分子量: 365.097
• InChiKey: RXYZQHSTEVSPMM-FNORWQNLSA-N

物化性质

• 沸点：
  525.7±50.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N-(5-bromopentyl)-3-(3,4-dichlorophenyl)acrylamide 在 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 3-phenyl-2-propenamides as inhibitors of glycogen phosphorylase a

  摘要：

  A series of 3-phenyl-2-propenamides discovered from a high-throughput screening campaign as novel, potent, glucosesensitive inhibitors of human liver glycogen phosphorylase a is described. A solid-phase synthesis on DMHB resin was also developed which provided efficient access not only to certain analogues that could not be cleanly made using more traditional means, but also to a variety of additional analogues. The SAR scope and synthetic strategy are presented herein. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.055
• 作为产物：
  描述：

  (E)-3-(3,4-二氯苯基)丙烯酸 在 草酰氯 、 四溴化碳 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 7.5h， 生成 (E)-N-(5-bromopentyl)-3-(3,4-dichlorophenyl)acrylamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 3-phenyl-2-propenamides as inhibitors of glycogen phosphorylase a

  摘要：

  A series of 3-phenyl-2-propenamides discovered from a high-throughput screening campaign as novel, potent, glucosesensitive inhibitors of human liver glycogen phosphorylase a is described. A solid-phase synthesis on DMHB resin was also developed which provided efficient access not only to certain analogues that could not be cleanly made using more traditional means, but also to a variety of additional analogues. The SAR scope and synthetic strategy are presented herein. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.055

文献信息

• CCR2B receptor antagonists: conversion of a weak HTS hit to a potent lead compound
  作者：Ian T Forbes、David G Cooper、Emma K Dodds、Deirdre M.B Hickey、Robert J Ife、Malcolm Meeson、Martin Stockley、Theo A Berkhout、Jayneeta Gohil、Pieter H.E Groot、Kitty Moores

  DOI：10.1016/s0960-894x(00)00347-4

  日期：2000.8

  A weak HTS hit at the CCR2B receptor has been converted into a potent antagonist by array SAR studies. Selectivity over the closely related CCR5 receptor is also achieved. (C) 2000 Elsevier Science Ltd. All rights reserved.
• CCR2:  Characterization of the Antagonist Binding Site from a Combined Receptor Modeling/Mutagenesis Approach
  作者：Theo A. Berkhout、Frank E. Blaney、Angela M. Bridges、David G. Cooper、Ian T. Forbes、Andrew D. Gribble、Pieter H. E. Groot、Adam Hardy、Robert J. Ife、Rejbinder Kaur、Kitty E. Moores、Helen Shillito、Jennifer Willetts、Jason Witherington

  DOI：10.1021/jm030862l

  日期：2003.9.1

  We describe here a classical molecular modeling exercise that was carried out to provide a basis for the design of novel antagonist ligands of the CCR2 receptor. Using a theoretical model of the CCR2 receptor, docking studies were carried out to define plausible binding modes for the various known antagonist ligands, including our own series of indole piperidine compounds. On the basis of these results, a number of site-directed mutations (SDM) were designed that were intended to verify the proposed docking models. From these it was clear that further refinements would be necessary in the model. This was aided by the publication of a crystal structure of bovine enabled us to define ligand-docking hypotheses that were in complete agreement with the results of the SDM experiments.
• Synthesis and structure–activity relationships of 3-phenyl-2-propenamides as inhibitors of glycogen phosphorylase a
  作者：Yue H. Li、Frank T. Coppo、Karen A. Evans、Todd L. Graybill、Mehul Patel、Jennifer Gale、Hu Li、Francis Tavares、Stephen A. Thomson

  DOI：10.1016/j.bmcl.2006.08.055

  日期：2006.11

  A series of 3-phenyl-2-propenamides discovered from a high-throughput screening campaign as novel, potent, glucosesensitive inhibitors of human liver glycogen phosphorylase a is described. A solid-phase synthesis on DMHB resin was also developed which provided efficient access not only to certain analogues that could not be cleanly made using more traditional means, but also to a variety of additional analogues. The SAR scope and synthetic strategy are presented herein. (c) 2006 Elsevier Ltd. All rights reserved.