2,3-dihydroxyacetanilide | 93525-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,3-dihydroxyacetanilide
• 英文别名: acetic acid-(2,3-dihydroxy-anilide)；Essigsaeure-(2,3-dihydroxy-anilid)；3-Acetamino-brenzcatechin；N-(2,3-Dihydroxyphenyl)acetamide
• CAS: 93525-21-4
• 化学式: C₈H₉NO₃
• 分子量: 167.164
• InChiKey: KSBUQEFHSPPNDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2,3-二甲氧基苯基)乙酰胺 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2,3-dihydroxyacetanilide
  参考文献：
  名称：

  Acetamidoquinone and acetamidohydroxy derivatives as inhibitors for both dihydroxyacetamido epoxidase and dehydrogenase

  摘要：

  A series of monohydroxy and dihydroxyacetanilides, acetamidoquinones and bromoacetamidoquinones have been synthesised and tested as substrates and/or inhibitors of highly purified dihydroxyacetamido epoxidase (DHAE) and dihydroxy acetamido dehydrogenase (DHADH) from Streptomyces LL-C10337. None was found to act as substrates but many selectively inhibit the enzymes. Kinetic analysis has shown that all the compounds act as reversible competitive inhibitors with respect to the substrates 2,5-dihydroxyacetanilide and 2,3-epoxy-1,4-benzoquinone-5-acetanilide. Monohydroxy acetanilides. showed weak inhibition to these enzymes compared to the dihydroxy derivatives while the more powerful inhibitors were the benzoquinoneacetanilide and its 5-bromo equivalent. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00403-5

文献信息

• THE REDUCTION OF MONONITROPYROCATECHOLS¹
  作者：John E. Foglesong、I. L. Newell

  DOI：10.1021/ja01365a060

  日期：1930.2
• Acetamidoquinone and acetamidohydroxy derivatives as inhibitors for both dihydroxyacetamido epoxidase and dehydrogenase
  作者：Chris G. Whiteley

  DOI：10.1016/s0968-0896(01)00403-5

  日期：2002.5

  A series of monohydroxy and dihydroxyacetanilides, acetamidoquinones and bromoacetamidoquinones have been synthesised and tested as substrates and/or inhibitors of highly purified dihydroxyacetamido epoxidase (DHAE) and dihydroxy acetamido dehydrogenase (DHADH) from Streptomyces LL-C10337. None was found to act as substrates but many selectively inhibit the enzymes. Kinetic analysis has shown that all the compounds act as reversible competitive inhibitors with respect to the substrates 2,5-dihydroxyacetanilide and 2,3-epoxy-1,4-benzoquinone-5-acetanilide. Monohydroxy acetanilides. showed weak inhibition to these enzymes compared to the dihydroxy derivatives while the more powerful inhibitors were the benzoquinoneacetanilide and its 5-bromo equivalent. (C) 2002 Elsevier Science Ltd. All rights reserved.