(2E,2'E)-N,N'-heptane-1,7-diylbis[3-(3,4-dichlorophenyl)acrylamide] | 1075623-21-0

• 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,2'E)-N,N'-heptane-1,7-diylbis[3-(3,4-dichlorophenyl)acrylamide]
• 英文别名: (2E,2''E)-N,N''-Heptane-1,7-diylbis[3-(3,4-dichlorophenyl)-acrylamide]；(E)-3-(3,4-dichlorophenyl)-N-[7-[[(E)-3-(3,4-dichlorophenyl)prop-2-enoyl]amino]heptyl]prop-2-enamide
• CAS: 1075623-21-0
• 化学式: C₂₅H₂₆Cl₄N₂O₂
• 分子量: 528.306
• InChiKey: IHCYEHCZFUDJBS-QHKWOANTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,7-二氨基庚烷 、 (E)-3-(3,4-二氯苯基)丙烯酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到(2E,2'E)-N,N'-heptane-1,7-diylbis[3-(3,4-dichlorophenyl)acrylamide]
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of bis-3-(3,4-dichlorophenyl)acrylamide derivatives as glycogen phosphorylase inhibitors

  摘要：

  During our research using a high-throughput screening system for discovery of a new class of human liver glycogen phosphorylase a (hLGPa) inhibitors, a series of 3-(3,4-dichlorophenyl)acrylamide derivatives were synthesized, and their inhibitory activities toward hLGPa were evaluated. Among the derivatives, (2E,2'E)-N,N'-pentane-1,5-diylbis[3-(3,4-dichlorophenyl)acrylamide] (6c) inhibited hLGPa with an IC50 value of 0.023 mu M. An X-ray crystallographic study of the enzyme-6c complex showed that the inhibitor is bound at the dimer interface site, where the 3,4-dichlorophenyl moiety interacts hydrophobically with the enzyme. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.010

文献信息

• Synthesis and pharmacological evaluation of bis-3-(3,4-dichlorophenyl)acrylamide derivatives as glycogen phosphorylase inhibitors
  作者：Kenichi Onda、Ryota Shiraki、Yasuhiro Yonetoku、Kazuhiro Momose、Naoko Katayama、Masaya Orita、Tomohiko Yamaguchi、Mitsuaki Ohta、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2008.08.010

  日期：2008.9

  During our research using a high-throughput screening system for discovery of a new class of human liver glycogen phosphorylase a (hLGPa) inhibitors, a series of 3-(3,4-dichlorophenyl)acrylamide derivatives were synthesized, and their inhibitory activities toward hLGPa were evaluated. Among the derivatives, (2E,2'E)-N,N'-pentane-1,5-diylbis[3-(3,4-dichlorophenyl)acrylamide] (6c) inhibited hLGPa with an IC50 value of 0.023 mu M. An X-ray crystallographic study of the enzyme-6c complex showed that the inhibitor is bound at the dimer interface site, where the 3,4-dichlorophenyl moiety interacts hydrophobically with the enzyme. (C) 2008 Elsevier Ltd. All rights reserved.