5-(2-氨基乙基)-3-甲基苯-1,2,4-三醇 | 41241-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 5-(2-氨基乙基)-3-甲基苯-1,2,4-三醇
• 英文名称: 5-(2-aminoethyl)-3-methylbenzene-1,2,4-triol
• 英文别名: 5-(2-Aminoethyl)-3-methylbenzene-1,2,4-triol
• CAS: 41241-42-3
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: VFBWQQWVDKMENN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2,4,5-三甲氧基-3-甲基苯基)乙胺 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 5-(2-氨基乙基)-3-甲基苯-1,2,4-三醇
  参考文献：
  名称：

  Catechol O-methyltransferase. 9. Mechanism of inactivation by 6-hydroxydopamine

  摘要：

  A series of methylated analogues of 6-hydroxydopamine (6-OHDA) has been synthesized and evaluated as irreversible inhibitors of catechol O-methyltransferase (COMT). These analogues have been prepared in an effort to elucidate the mechanism involved in the inactivation of this enzyme by 6-OHDA. The analogues prepared had methyl groups incorporated in the 2 and/or 5 positions of 6-OHDA so as to block nucleophilic attakc at these positions in the corresponding oxidation products [6-hydroxydopamine-p-quinone (6-OHDAQ), aminochromes I and II]. Such 2- and/or 5-methylated 6-OHDA analogues were found to be inhibitors of COMT with the inactivation apparently resulting from modification of an essential amino acid residue at the active site of the enzyme. The activity of these analogues as inhibitors of COMT argues against a mechanism involving a 1,4 Michael addition reaction by a protein nucleophile at the 2 or 5 positions on 6-OHDAQ or on the corresponding aminochromes. Instead, an alternative mechanism is proposed to explain these data, which involves attack of a protein nucleophile at the carbonyl group in the 6 position of 6-OHDAQ or at the imine functionality on aminochromes I and II. The results of the present experiments have provided insight into the mechanism involved in inactivation of COMT by 6-OHDA. In addition, this study has provided considerable insight into the chemical reactivity of the electrophilic species generated after oxidation of 6-OHDA.

  DOI：

  10.1021/jm00232a007

文献信息

• Oxygen permeable polymers, ionomers and methods of making the same
  申请人：Nissan North America, Inc.

  公开号：US10259894B1

  公开（公告）日：2019-04-16

  An oxygen permeable polymer has the following formula: wherein RS is a non-sulfonyl halide portion of a sulfonyl halide monomer or polymer; XP is —NH or —NHCO; A is an optionally substituted alkyl; L is 0, 1 or 2; m is 2 or 3; Z is H or CH3; and n is 5-m. The polymer can be used in air separation devices, air concentrators, and in electrodes for electrochemical devices.

  透氧聚合物的分子式如下 其中 RS 是磺酰卤单体或聚合物的非磺酰卤部分；XP 是-NH 或-NHCO；A 是任选取代的烷基；L 是 0、1 或 2；m 是 2 或 3；Z 是 H 或 CH3；n 是 5-m。这种聚合物可用于空气分离装置、空气浓缩器和电化学装置的电极。
• Oxygen Permeable Monomers, Polymers and Ionomers and Methods of Making the Same
  申请人：Nissan North America, Inc.

  公开号：US20190092882A1

  公开（公告）日：2019-03-28

  An oxygen permeable polymer has the following formula: wherein R S is a non-sulfonyl halide portion of a sulfonyl halide monomer or polymer; X P is —NH or —NHCO; A is an optionally substituted alkyl; L is 0, 1 or 2; m is 2 or 3; Z is H or CH 3 ; and n is 5−m. The polymer can be used in air separation devices, air concentrators, and in electrodes for electrochemical devices.
• Catechol O-methyltransferase. 9. Mechanism of inactivation by 6-hydroxydopamine
  作者：R. T. Borchardt、J. R. Reid、D. R. Thakker、Y. O. Liang、R. W. Wightman、R. N. Adams

  DOI：10.1021/jm00232a007

  日期：1976.10

  A series of methylated analogues of 6-hydroxydopamine (6-OHDA) has been synthesized and evaluated as irreversible inhibitors of catechol O-methyltransferase (COMT). These analogues have been prepared in an effort to elucidate the mechanism involved in the inactivation of this enzyme by 6-OHDA. The analogues prepared had methyl groups incorporated in the 2 and/or 5 positions of 6-OHDA so as to block nucleophilic attakc at these positions in the corresponding oxidation products [6-hydroxydopamine-p-quinone (6-OHDAQ), aminochromes I and II]. Such 2- and/or 5-methylated 6-OHDA analogues were found to be inhibitors of COMT with the inactivation apparently resulting from modification of an essential amino acid residue at the active site of the enzyme. The activity of these analogues as inhibitors of COMT argues against a mechanism involving a 1,4 Michael addition reaction by a protein nucleophile at the 2 or 5 positions on 6-OHDAQ or on the corresponding aminochromes. Instead, an alternative mechanism is proposed to explain these data, which involves attack of a protein nucleophile at the carbonyl group in the 6 position of 6-OHDAQ or at the imine functionality on aminochromes I and II. The results of the present experiments have provided insight into the mechanism involved in inactivation of COMT by 6-OHDA. In addition, this study has provided considerable insight into the chemical reactivity of the electrophilic species generated after oxidation of 6-OHDA.