(S)-(5-(benzyloxy)-1-octyl-4-oxo-1,4-dihydropyridin-2-yl)methyl 2-amino-3-phenylpropanoate hydrochloride

• 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: (S)-(5-(benzyloxy)-1-octyl-4-oxo-1,4-dihydropyridin-2-yl)methyl 2-amino-3-phenylpropanoate hydrochloride
• 英文别名: (5-hydroxy-1-octyl-4-oxopyridin-2-yl)methyl (2S)-2-amino-3-phenylpropanoate;hydrochloride
• 化学式: C₂₃H₃₂N₂O₄*(x)ClH
• 分子量: 437.0
• InChiKey: AQBSLBVJKUAJJG-BDQAORGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  92.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-(5-(benzyloxy)-1-octyl-4-oxo-1,4-dihydropyridin-2-yl)methyl 2-(benzyloxycarbonyl)-3-phenylpropanoate 在 5%-palladium/activated carbon 、 氢气 、 氯化苄 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 生成 (S)-(5-(benzyloxy)-1-octyl-4-oxo-1,4-dihydropyridin-2-yl)methyl 2-amino-3-phenylpropanoate hydrochloride
  参考文献：
  名称：

  Design and Synthesis of Hydroxypyridinone-l-phenylalanine Conjugates as Potential Tyrosinase Inhibitors

  摘要：

  A range of hydroxypyridinone-L-phenylalanine conjugates were synthesized starting from kojic acid. Their tyrosinase activity was determined, and it was found that one of the compounds ((S)-(5-(benzyloxy)-1-octyl-4-oxo-1,4-dihydropyridin-2-yl)methyl 2-amino-3-phenylpropanoate, 5e) showed potent inhibitory effect against mushroom tyrosinase, the IC50 values for monophenolase and diphenolase activities being 12.6 and 4.0 mu M, respectively. It was also demonstrated that these conjugates are mixed-type inhibitors, suggesting they could bind to both the free enzyme and the enzyme substrate complexes. MTT assay indicated that Se was nontoxic to three cell lines. This compound may find applications in food preservation and cosmetics.

  DOI：

  10.1021/jf401585f

文献信息

• Design and Synthesis of Hydroxypyridinone-<scp>l</scp>-phenylalanine Conjugates as Potential Tyrosinase Inhibitors
  作者：Dong-Fang Li、Pan-Pan Hu、Mu-Song Liu、Xiao-Le Kong、Jin-Chao Zhang、Robert C. Hider、Tao Zhou

  DOI：10.1021/jf401585f

  日期：2013.7.10

  A range of hydroxypyridinone-L-phenylalanine conjugates were synthesized starting from kojic acid. Their tyrosinase activity was determined, and it was found that one of the compounds ((S)-(5-(benzyloxy)-1-octyl-4-oxo-1,4-dihydropyridin-2-yl)methyl 2-amino-3-phenylpropanoate, 5e) showed potent inhibitory effect against mushroom tyrosinase, the IC50 values for monophenolase and diphenolase activities being 12.6 and 4.0 mu M, respectively. It was also demonstrated that these conjugates are mixed-type inhibitors, suggesting they could bind to both the free enzyme and the enzyme substrate complexes. MTT assay indicated that Se was nontoxic to three cell lines. This compound may find applications in food preservation and cosmetics.