(2S)-2-[3-(3,4-dihydroxyphenyl)propanoylamino]-N-hydroxy-3-phenylpropanamide | 1418498-42-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-[3-(3,4-dihydroxyphenyl)propanoylamino]-N-hydroxy-3-phenylpropanamide
• CAS: 1418498-42-6
• 化学式: C₁₈H₂₀N₂O₅
• 分子量: 344.367
• InChiKey: ZCLPSRKJIIJBOB-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二羟基苯基丙酸 、 Fmoc-L-苯丙氨酸 在 4-O-methylhydroxylaminephenoxymethyl-copoly(styrene-1%-divinylbenzene)-resin 、 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 哌啶 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 1.88h， 生成 (2S)-2-[3-(3,4-dihydroxyphenyl)propanoylamino]-N-hydroxy-3-phenylpropanamide
  参考文献：
  名称：

  Synthesis and dual biological effects of hydroxycinnamoyl phenylalanyl/prolyl hydroxamic acid derivatives as tyrosinase inhibitor and antioxidant

  摘要：

  We previously reported that caffeoyl-amino acidyl-hydroxamic acid (CA-Xaa-NHOH) acted as both a good antioxidant and tyrosinase inhibitor, in particular when caffeic acid was conjugated with proline or amino acids having aromatic ring like phenylalanine. Here, various hydroxycinnamic acid (HCA) derivatives were further conjugated with phenylalanyl hydroxamic acid and prolyl hydroxamic acid (HCA-Phe-NHOH and HCA-Pro-NHOH) to study the structure and activity relationship as both antioxidants and tyrosinase inhibitors. When their biological activities were evaluated, all HCA-Phe-NHOH and HCA-Pro-NHOH exhibited enhanced antioxidant activity compared to HCA alone. Moreover, derivatives of caffeic acid, ferulic acid, and sinapic acid inhibited lipid peroxidation more efficiently than vitamin E analogue (Trolox). In addition, derivatives of caffeic acid and sinapic acid efficiently inhibited tyrosinase activity and reduced melanin content in melanocytes Mel-Ab cell. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.107

文献信息

• Synthesis and dual biological effects of hydroxycinnamoyl phenylalanyl/prolyl hydroxamic acid derivatives as tyrosinase inhibitor and antioxidant
  作者：Seon-Yeong Kwak、Jin-Kyoung Yang、Hye-Ryung Choi、Kyung-Chan Park、Young-Bu Kim、Yoon-Sik Lee

  DOI：10.1016/j.bmcl.2012.10.107

  日期：2013.2

  We previously reported that caffeoyl-amino acidyl-hydroxamic acid (CA-Xaa-NHOH) acted as both a good antioxidant and tyrosinase inhibitor, in particular when caffeic acid was conjugated with proline or amino acids having aromatic ring like phenylalanine. Here, various hydroxycinnamic acid (HCA) derivatives were further conjugated with phenylalanyl hydroxamic acid and prolyl hydroxamic acid (HCA-Phe-NHOH and HCA-Pro-NHOH) to study the structure and activity relationship as both antioxidants and tyrosinase inhibitors. When their biological activities were evaluated, all HCA-Phe-NHOH and HCA-Pro-NHOH exhibited enhanced antioxidant activity compared to HCA alone. Moreover, derivatives of caffeic acid, ferulic acid, and sinapic acid inhibited lipid peroxidation more efficiently than vitamin E analogue (Trolox). In addition, derivatives of caffeic acid and sinapic acid efficiently inhibited tyrosinase activity and reduced melanin content in melanocytes Mel-Ab cell. (C) 2012 Elsevier Ltd. All rights reserved.