(2E,2'E)-N,N'-(thiodiethane-2,1-diyl)bis[3-(3,4-dichlorophenyl)acrylamide] hydrochloride | 1075623-35-6

• 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'-(thiodiethane-2,1-diyl)bis[3-(3,4-dichlorophenyl)acrylamide] hydrochloride
• 英文别名: (E)-3-(3,4-dichlorophenyl)-N-[2-[2-[[(E)-3-(3,4-dichlorophenyl)prop-2-enoyl]amino]ethylsulfanyl]ethyl]prop-2-enamide
• CAS: 1075623-35-6
• 化学式: C₂₂H₂₀Cl₄N₂O₂S
• 分子量: 518.291
• InChiKey: ZTQGUZMRJMYXNB-FCXRPNKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,2'E)-N,N'-(thiodiethane-2,1-diyl)bis[3-(3,4-dichlorophenyl)acrylamide] hydrochloride 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以70%的产率得到(2E,2'E)-N,N'-(sulfinyldiethane-2,1-diyl)bis[3-(3,4-dichlorophenyl)acrylamide] hydrochloride
  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
• 作为产物：
  描述：

  氨乙基硫醚 、 (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92%的产率得到(2E,2'E)-N,N'-(thiodiethane-2,1-diyl)bis[3-(3,4-dichlorophenyl)acrylamide] hydrochloride
  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