N-[2-(3,4-dihydroxyphenyl)ethyl]-2-(4-hydroxy-3-methoxyphenyl)acetamide | 886037-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-[2-(3,4-dihydroxyphenyl)ethyl]-2-(4-hydroxy-3-methoxyphenyl)acetamide
• CAS: 886037-62-3
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: FAYGSEKNOJLNLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(3,4-dihydroxyphenyl)ethyl]-2-(4-hydroxy-3-methoxyphenyl)acetamide 在 盐酸 、 sodium tetrahydroborate 、 potassium carbonate 、 三氯氧磷 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 82.83h， 生成 6,7-dihydroxy-1-(4-hydroxy-3-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride
  参考文献：
  名称：

  哺乳动物生物碱。8.四氢罂粟碱相关的1-苄基四氢异喹啉的合成及其生物学效应。

  摘要：

  DOI：

  10.1021/jm00180a013
• 作为产物：
  描述：

  多巴胺 、 高香草酸 反应 2.0h， 生成 N-[2-(3,4-dihydroxyphenyl)ethyl]-2-(4-hydroxy-3-methoxyphenyl)acetamide
  参考文献：
  名称：

  哺乳动物生物碱。8.四氢罂粟碱相关的1-苄基四氢异喹啉的合成及其生物学效应。

  摘要：

  DOI：

  10.1021/jm00180a013

文献信息

• Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase
  作者：Sabrina Okombi、Delphine Rival、Sébastien Bonnet、Anne-Marie Mariotte、Eric Perrier、Ahcène Boumendjel

  DOI：10.1016/j.bmcl.2006.01.022

  日期：2006.4

  Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin synthesis, catalyzing the transformation of tyrosine to L-dopaquinone. The aim of the present study was to study molecules able to inhibit melanin synthesis through inhibition of tyrosinase and their potential use in treating pigmentation-related disorders. We targeted amides obtained from coupling p-hydroxycinnamic acid derivatives with phenylalkylamines. The biological activity was evaluated on human melanocytes by an assay which measures tyrosine-catalyzed L-Dopa oxidation. The most active amides were: trans-N-caffeoyltyramine, N-dihydrocaffeoyltyramine, and trans-N-dihydro-p-hydroxycinnamoyltyramine which induce complete inhibition at 0.1 mM. At the latter concentration, kojic acid, which was used as the reference inhibitor, was inactive. (C) 2006 Elsevier Ltd. All rights reserved.