3-(2-methoxyphenyl)-N-(2-morpholin-4-ylethyl)prop-2-enamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(2-methoxyphenyl)-N-(2-morpholin-4-ylethyl)prop-2-enamide
• 化学式: C₁₆H₂₂N₂O₃
• 分子量: 290.362
• InChiKey: FDOMVLYSWUBPOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻甲氧基苯甲醛 在 吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 49.0h， 生成 3-(2-methoxyphenyl)-N-(2-morpholin-4-ylethyl)prop-2-enamide
  参考文献：
  名称：

  Novel morpholine containing cinnamoyl amides as potent tyrosinase inhibitors

  摘要：

  Tyrosinase enzyme plays a crucial role in melanin biosynthesis and enzymatic browning process of vegetables and fruits. Hence, tyrosinase inhibitors are important in the fields of medicine, cosmetics and agriculture. In this study, novel N-(2-morpholinoethyl)cinnamamide derivatives bearing different substituents on phenyl ring were designed, synthesized and evaluated for their tyrosinase diphenolase inhibitory activity. The compounds were found to be better tyrosinase inhibitors (lC(50)s were in micro molar range) than cinnamic acid. (E)-3-(3-chlorophenyl)-N-(2-morpholinoethyl)acrylamide (B6) exhibited the highest inhibition with IC50 value of 15.2 +/- 0.6 mu M which was comparable to that of kojic acid. The inhibition kinetic analysis of B6 indicated that the compound was a mixed-type tyrosinase inhibitor. In silico ADME prediction indicated that B6 might show more skin penetration than kojic acid. Molecular docking analysis confirmed that the active inhibitors well accommodated in the mushroom tyrosinase active site and it was also revealed that B6 formed the most stable drug-receptor complex with the target protein. Therefore, cinnamamide B6 could be introduced as a potent tyrosinase inhibitor that might be a promising lead in cosmetics, medicine and food industry. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijbiomac.2019.05.201

文献信息

• Novel morpholine containing cinnamoyl amides as potent tyrosinase inhibitors
  作者：Shahrzad Ghafary、Sara Ranjbar、Bagher Larijani、Mohsen Amini、Mahmood Biglar、Mohammad Mahdavi、Maryam Bakhshaei、Mahsima Khoshneviszadeh、Amirhossein Sakhteman、Mehdi Khoshneviszadeh

  DOI：10.1016/j.ijbiomac.2019.05.201

  日期：2019.8

  Tyrosinase enzyme plays a crucial role in melanin biosynthesis and enzymatic browning process of vegetables and fruits. Hence, tyrosinase inhibitors are important in the fields of medicine, cosmetics and agriculture. In this study, novel N-(2-morpholinoethyl)cinnamamide derivatives bearing different substituents on phenyl ring were designed, synthesized and evaluated for their tyrosinase diphenolase inhibitory activity. The compounds were found to be better tyrosinase inhibitors (lC(50)s were in micro molar range) than cinnamic acid. (E)-3-(3-chlorophenyl)-N-(2-morpholinoethyl)acrylamide (B6) exhibited the highest inhibition with IC50 value of 15.2 +/- 0.6 mu M which was comparable to that of kojic acid. The inhibition kinetic analysis of B6 indicated that the compound was a mixed-type tyrosinase inhibitor. In silico ADME prediction indicated that B6 might show more skin penetration than kojic acid. Molecular docking analysis confirmed that the active inhibitors well accommodated in the mushroom tyrosinase active site and it was also revealed that B6 formed the most stable drug-receptor complex with the target protein. Therefore, cinnamamide B6 could be introduced as a potent tyrosinase inhibitor that might be a promising lead in cosmetics, medicine and food industry. (C) 2019 Elsevier B.V. All rights reserved.