2-Chloro-1-(2-hydroxy-3-methoxyphenyl)ethan-1-one | 75717-52-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Chloro-1-(2-hydroxy-3-methoxyphenyl)ethan-1-one
• 英文别名: 2-chloro-1-(2-hydroxy-3-methoxyphenyl)ethanone
• CAS: 75717-52-1
• 化学式: C₉H₉ClO₃
• 分子量: 200.622
• InChiKey: RNTRTDQNTISDFU-UHFFFAOYSA-N

物化性质

• 熔点：
  97.5-98 °C
• 沸点：
  292.5±25.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2-Chloro-1-(2-hydroxy-3-methoxyphenyl)ethan-1-one 在 sodium acetate 作用下， 以 甲醇 为溶剂， 生成 7-甲氧基-3(2H)-苯并呋喃酮
  参考文献：
  名称：

  Structure-Based Design Leads to the Identification of Lithium Mimetics That Block Mania-like Effects in Rodents. Possible New GSK-3β Therapies for Bipolar Disorders

  摘要：

  More than two million American adults, or approximately one percent of the population 18 years or older, suffer from bipolar disorder. Current treatments include the so-called "mood stabilizers," lithium and valproic acid. Both are relatively dated drugs that are only partially effective and produce various undesirable side effects including weight gain. Based upon continued efforts to understand the molecular target for lithium, it now appears that specific inhibitors of the enzyme glycogen synthase kinase-3 beta (GSK-3 beta) may mimic the therapeutic action of mood stabilizers and might therefore allow for the design of improved drugs for treating patients with bipolar disorder as well as certain neurodegenerative disorders. Furthermore, the pro-apoptotic properties of the GSK-3 enzyme suggest the possible use of such inhibitors as neuroprotective agents. In fact, neuroprotection may contribute to the treatment of mood disorders. The present chemistry, modeling, and biology efforts have identified 3-benzofuranyl-4-indolylmaleimides as potent and relatively selective GSK-3 beta inhibitors. The best ligand in this series (having a K-i value of 4.6 nM against GSK-3 beta) was studied in a novel mouse model of mania that has recently been validated with several clinically effective mood stabilizers. This study presents the first demonstration of the efficacy of a GSK-3 beta inhibitor in this mouse model of mania. Selective brain penetrable GSK-3 ligands like those described herein become valuable research tools in better defining the role of this multifaceted kinase in both physiological and pathophysiological events.

  DOI：

  10.1021/ja068969w
• 作为产物：
  描述：

  木榴油 、 氯乙酰氯 在 三氯化铝 作用下， 生成 2-Chloro-1-(2-hydroxy-3-methoxyphenyl)ethan-1-one
  参考文献：
  名称：

  Structure-Based Design Leads to the Identification of Lithium Mimetics That Block Mania-like Effects in Rodents. Possible New GSK-3β Therapies for Bipolar Disorders

  摘要：

  More than two million American adults, or approximately one percent of the population 18 years or older, suffer from bipolar disorder. Current treatments include the so-called "mood stabilizers," lithium and valproic acid. Both are relatively dated drugs that are only partially effective and produce various undesirable side effects including weight gain. Based upon continued efforts to understand the molecular target for lithium, it now appears that specific inhibitors of the enzyme glycogen synthase kinase-3 beta (GSK-3 beta) may mimic the therapeutic action of mood stabilizers and might therefore allow for the design of improved drugs for treating patients with bipolar disorder as well as certain neurodegenerative disorders. Furthermore, the pro-apoptotic properties of the GSK-3 enzyme suggest the possible use of such inhibitors as neuroprotective agents. In fact, neuroprotection may contribute to the treatment of mood disorders. The present chemistry, modeling, and biology efforts have identified 3-benzofuranyl-4-indolylmaleimides as potent and relatively selective GSK-3 beta inhibitors. The best ligand in this series (having a K-i value of 4.6 nM against GSK-3 beta) was studied in a novel mouse model of mania that has recently been validated with several clinically effective mood stabilizers. This study presents the first demonstration of the efficacy of a GSK-3 beta inhibitor in this mouse model of mania. Selective brain penetrable GSK-3 ligands like those described herein become valuable research tools in better defining the role of this multifaceted kinase in both physiological and pathophysiological events.

  DOI：

  10.1021/ja068969w

文献信息

• Exclusive ortho .alpha.-chloroacetylation of phenols
  作者：Tatsuo Toyoda、Kazuyuki Sasakura、Tsutomu Sugasawa

  DOI：10.1021/jo00314a046

  日期：1981.1
• TOYODA TATSUO; SASAKURA KAZUYUKI; SUGASAWA TSUTOMU, J. ORG. CHEM., 1981, 46, NO 1, 189-191
  作者：TOYODA TATSUO、 SASAKURA KAZUYUKI、 SUGASAWA TSUTOMU

  DOI：——

  日期：——