2-乙酰氧基-5-羟基苯乙酮 | 144152-29-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙酰氧基-5-羟基苯乙酮
• 英文名称: 2-acetoxy-5-hydroxyacetophenone
• 英文别名: (2-acetyl-4-hydroxyphenyl) acetate
• CAS: 144152-29-4
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: ALCWHITWIVGRQB-UHFFFAOYSA-N

物化性质

• 熔点：
  105–106°C

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-乙酰氧基-5-羟基苯乙酮 在 phenyltrimethylammonium tribromide 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 9.0h， 生成 5-羟基-3(2H)-苯并呋喃酮
  参考文献：
  名称：

  Discovery of Naturally Occurring Aurones That Are Potent Allosteric Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase

  摘要：

  We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC(50) below 5 mu M and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indo1-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC(50) of 2.2 mu M. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.

  DOI：

  10.1021/jm200242p
• 作为产物：
  描述：

  2,5-diacetoxyacetophenone 以 四氢呋喃 、 正丁醇 为溶剂， 反应 45.0h， 以60%的产率得到2-乙酰氧基-5-羟基苯乙酮
  参考文献：
  名称：

  有机溶剂中脂肪酶对聚乙酰氧基芳基-甲基酮的区域选择性脱酰作用

  摘要：

  悬浮在有机溶剂中的猪胰腺和假丝酵母念珠菌的脂肪酶已用于研究聚乙酰氧基苯乙酮的区域选择性脱酰作用。已经观察到乙酸酯基团在邻位以外的位置上的水解是主要的。

  DOI：

  10.1016/s0040-4020(01)88239-9

文献信息

• Regioselective deacylation of polyacetoxy aryl-methyl ketones by lipases in organic solvents
  作者：Vs Parmar、Ak Prasad、Nk Sharma、Sk Singh、Hn Pati、Suman Gupta

  DOI：10.1016/s0040-4020(01)88239-9

  日期：1992.1

  Lipases from porcine pancreas and Candida cylindraea, suspended in organic solvents have been used to study regioselective deacylation of polyacetoxy acetophenones. It has been observed that the hydrolysis of acetate groups at positions other than ortho predominates.

  悬浮在有机溶剂中的猪胰腺和假丝酵母念珠菌的脂肪酶已用于研究聚乙酰氧基苯乙酮的区域选择性脱酰作用。已经观察到乙酸酯基团在邻位以外的位置上的水解是主要的。
• Adam, Waldemar; Schulz, Manfred H., Chemische Berichte, 1992, vol. 125, # 11, p. 2455 - 2462
  作者：Adam, Waldemar、Schulz, Manfred H.

  DOI：——

  日期：——
• Parmar V. S., Khanduri C. H., Tyagi O. D., Prasad A. K., Gupta Suman, Bis+, Indian J. Chem. B, 31 (1992) N 12, S 925-929
  作者：Parmar V. S., Khanduri C. H., Tyagi O. D., Prasad A. K., Gupta Suman, Bis+

  DOI：——

  日期：——
• Discovery of Naturally Occurring Aurones That Are Potent Allosteric Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase
  作者：Romain Haudecoeur、Abdelhakim Ahmed-Belkacem、Wei Yi、Antoine Fortuné、Rozenn Brillet、Catherine Belle、Edwige Nicolle、Coralie Pallier、Jean-Michel Pawlotsky、Ahcène Boumendjel

  DOI：10.1021/jm200242p

  日期：2011.8.11

  We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC(50) below 5 mu M and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indo1-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC(50) of 2.2 mu M. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.
• Parmar, V S; Khanduri, C H; Tyagi, O D, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 12, p. 925 - 929
  作者：Parmar, V S、Khanduri, C H、Tyagi, O D、Prasad, A K、Gupta, Suman、et al.

  DOI：——

  日期：——