3-(2-chloro-4-hydroxy-phenyl)-acrylic acid methyl ester | 1380106-82-0

• 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: 3-(2-chloro-4-hydroxy-phenyl)-acrylic acid methyl ester
• 英文别名: Methyl 3-(2-chloro-4-hydroxyphenyl)prop-2-enoate；methyl 3-(2-chloro-4-hydroxyphenyl)prop-2-enoate
• CAS: 1380106-82-0
• 化学式: C₁₀H₉ClO₃
• 分子量: 212.633
• InChiKey: GXINESLRGQLYCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-chloro-4-hydroxy-phenyl)-acrylic acid methyl ester 在 水 、 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 60.0h， 生成 3-(2-chloro-4-isobutoxy-phenyl)-N-(tetrahydropyran-2-yloxy)-acrylamide
  参考文献：
  名称：

  Reexamining hydroxamate inhibitors of botulinum neurotoxin serotype A: Extending towards the β-exosite

  摘要：

  Botulinum neurotoxins (BoNTs) are the most toxic proteins known to man, exposure to which results in flaccid paralysis. Given their extreme potency, these proteins have become studied as possible weapons of bioterrorism; however, effective treatments that function after intoxication have not progressed to the clinic. Here, we have reexamined one of the most effective inhibitors, 2,4-dichlorocinnamyl hydroxamate, in the context of the known plasticity of the BoNT/A light chain metalloprotease. Our studies have shown that modifications of this compound are tolerated and result in improved inhibitors, with the best compound having an IC50 of 0.23 mu M. Given the inconsistency of structure-activity relationship trends observed across similar compounds, this data argues for caution in extrapolating across structural series (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.019
• 作为产物：
  描述：

  2-氯-4-羟基苯甲醛 在 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 3-(2-chloro-4-hydroxy-phenyl)-acrylic acid methyl ester
  参考文献：
  名称：

  Reexamining hydroxamate inhibitors of botulinum neurotoxin serotype A: Extending towards the β-exosite

  摘要：

  Botulinum neurotoxins (BoNTs) are the most toxic proteins known to man, exposure to which results in flaccid paralysis. Given their extreme potency, these proteins have become studied as possible weapons of bioterrorism; however, effective treatments that function after intoxication have not progressed to the clinic. Here, we have reexamined one of the most effective inhibitors, 2,4-dichlorocinnamyl hydroxamate, in the context of the known plasticity of the BoNT/A light chain metalloprotease. Our studies have shown that modifications of this compound are tolerated and result in improved inhibitors, with the best compound having an IC50 of 0.23 mu M. Given the inconsistency of structure-activity relationship trends observed across similar compounds, this data argues for caution in extrapolating across structural series (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.019

文献信息

• Reexamining hydroxamate inhibitors of botulinum neurotoxin serotype A: Extending towards the β-exosite
  作者：Garry R. Smith、Dejan Caglič、Petr Čapek、Yan Zhang、Sujata Godbole、Allen B. Reitz、Tobin J. Dickerson

  DOI：10.1016/j.bmcl.2012.04.019

  日期：2012.6

  Botulinum neurotoxins (BoNTs) are the most toxic proteins known to man, exposure to which results in flaccid paralysis. Given their extreme potency, these proteins have become studied as possible weapons of bioterrorism; however, effective treatments that function after intoxication have not progressed to the clinic. Here, we have reexamined one of the most effective inhibitors, 2,4-dichlorocinnamyl hydroxamate, in the context of the known plasticity of the BoNT/A light chain metalloprotease. Our studies have shown that modifications of this compound are tolerated and result in improved inhibitors, with the best compound having an IC50 of 0.23 mu M. Given the inconsistency of structure-activity relationship trends observed across similar compounds, this data argues for caution in extrapolating across structural series (C) 2012 Elsevier Ltd. All rights reserved.