5'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone | 81325-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone
• 英文别名: 2-hydroxy-4,6-dimethoxy-5-chloroacetophenone；1-(3-Chloro-6-hydroxy-2,4-dimethoxyphenyl)ethanone
• CAS: 81325-86-2
• 化学式: C₁₀H₁₁ClO₄
• 分子量: 230.648
• InChiKey: QMUAUQUQQYNWIM-UHFFFAOYSA-N

物化性质

• 熔点：
  193–194°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(苄氧基)-3-氯苯甲醛 、 5'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以54.5%的产率得到2'-hydroxy-3,5'-dichloro-4',6'-dimethoxy-4-benzyloxychalcone
  参考文献：
  名称：

  Levai, Albert; Tokes, Adrienne L., Synthetic Communications, 1982, vol. 12, # 9, p. 701 - 708

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以39%的产率得到5'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone
  参考文献：
  名称：

  Synthesis of chlorinated flavonoids with anti-inflammatory and pro-apoptotic activities in human neutrophils

  摘要：

  Neutrophils are considered the central cells of acute inflammation. Flavonoids have been suggested as therapeutic agents to avoid damages induced by inflammatory processes. It is well known the reactivity of flavonoids with hypochlorous acid produced by neutrophils, to form stable mono and dichlorinated products. In this study, we synthesized novel chlorinated flavonoids and investigated their effect in neutrophils' oxidative burst and in its lifespan, in comparison with the parent non-chlorinated flavonoids. The obtained results demonstrate that chlorinated flavonoids were more efficient than their parent compounds in modulating neutrophils' oxidative burst in phorbol myristate acetate-activated neutrophils. Some of the tested flavonoids drive neutrophil apoptosis in a caspase 3-dependent fashion. The present data showed that 8-chloro-3',4',5,7-tetrahydroxyflavone (4a) constitute an alternative anti-inflammatory therapy, due to the proven ability to suppress mechanisms engaged at the onset and progression of inflammation. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.035

文献信息

• Nitration, amination, and halogenation of Di-O-methylphloracetophenone
  作者：John P. Acton、Dorothy J. Donnelly、John A. Donnelly

  DOI：10.1007/bf00814339

  日期：1982.1
• ACTON, J. P.;DONNELLY, D. J.;DONNELLY, J. A., MONATSH. CHEM., 1982, 113, N 1, 73-79
  作者：ACTON, J. P.、DONNELLY, D. J.、DONNELLY, J. A.

  DOI：——

  日期：——
• Synthesis of chlorinated flavonoids with anti-inflammatory and pro-apoptotic activities in human neutrophils
  作者：Marisa Freitas、Daniela Ribeiro、Sara M. Tomé、Artur M.S. Silva、Eduarda Fernandes

  DOI：10.1016/j.ejmech.2014.08.035

  日期：2014.10

  Neutrophils are considered the central cells of acute inflammation. Flavonoids have been suggested as therapeutic agents to avoid damages induced by inflammatory processes. It is well known the reactivity of flavonoids with hypochlorous acid produced by neutrophils, to form stable mono and dichlorinated products. In this study, we synthesized novel chlorinated flavonoids and investigated their effect in neutrophils' oxidative burst and in its lifespan, in comparison with the parent non-chlorinated flavonoids. The obtained results demonstrate that chlorinated flavonoids were more efficient than their parent compounds in modulating neutrophils' oxidative burst in phorbol myristate acetate-activated neutrophils. Some of the tested flavonoids drive neutrophil apoptosis in a caspase 3-dependent fashion. The present data showed that 8-chloro-3',4',5,7-tetrahydroxyflavone (4a) constitute an alternative anti-inflammatory therapy, due to the proven ability to suppress mechanisms engaged at the onset and progression of inflammation. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Levai, Albert; Tokes, Adrienne L., Synthetic Communications, 1982, vol. 12, # 9, p. 701 - 708
  作者：Levai, Albert、Tokes, Adrienne L.

  DOI：——

  日期：——