4-chloro-1-(2,5-dichlorothiophen-3-yl)butan-1-one | 84958-54-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-chloro-1-(2,5-dichlorothiophen-3-yl)butan-1-one
• CAS: 84958-54-3
• 化学式: C₈H₇Cl₃OS
• 分子量: 257.568
• InChiKey: IVPDIDRSLXLWHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,5-二氯噻吩 、 4-氯丁酰氯 在 aluminum (III) chloride 作用下， 以 二硫化碳 为溶剂， 以41%的产率得到4-chloro-1-(2,5-dichlorothiophen-3-yl)butan-1-one
  参考文献：
  名称：

  Thienylhalomethylketones: Irreversible glycogen synthase kinase 3 inhibitors as useful pharmacological tools

  摘要：

  Thienylhalomethylketones, whose chemical, biological, and pharmaceutical data are here reported, are the first irreversible inhibitors of GSK-3 beta described to date. Their inhibitory activity is likely related to the cysteine residue present in the ATP-binding site, which is proposed as a relevant residue for modulation of GSK-3 activity. The good cell permeability of the compounds allows them to be used in different cell models. Overall, the results presented here support the potential use of halomethylketones as pharmacological tools for the study of GSK-3 beta functions and suggest a new mechanism for GSK-3 beta inhibition that may be considered for further drug design. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.042

文献信息

• Thienylhalomethylketones: Irreversible glycogen synthase kinase 3 inhibitors as useful pharmacological tools
  作者：Daniel I. Perez、Santiago Conde、Concepción Pérez、Carmen Gil、Diana Simon、Francisco Wandosell、Francisco J. Moreno、José L. Gelpí、Francisco J. Luque、Ana Martínez

  DOI：10.1016/j.bmc.2009.08.042

  日期：2009.10

  Thienylhalomethylketones, whose chemical, biological, and pharmaceutical data are here reported, are the first irreversible inhibitors of GSK-3 beta described to date. Their inhibitory activity is likely related to the cysteine residue present in the ATP-binding site, which is proposed as a relevant residue for modulation of GSK-3 activity. The good cell permeability of the compounds allows them to be used in different cell models. Overall, the results presented here support the potential use of halomethylketones as pharmacological tools for the study of GSK-3 beta functions and suggest a new mechanism for GSK-3 beta inhibition that may be considered for further drug design. (C) 2009 Elsevier Ltd. All rights reserved.