5-(benzyloxy)-2-(hydroxymethyl)-1-octylpyridin-4(1H)-one | 1429744-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(benzyloxy)-2-(hydroxymethyl)-1-octylpyridin-4(1H)-one
• 英文别名: 2-(Hydroxymethyl)-1-octyl-5-phenylmethoxypyridin-4-one；2-(hydroxymethyl)-1-octyl-5-phenylmethoxypyridin-4-one
• CAS: 1429744-60-4
• 化学式: C₂₁H₂₉NO₃
• 分子量: 343.466
• InChiKey: XZTJEFFKWDJCFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-2-(hydroxymethyl)-1-octylpyridin-4(1H)-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  具铁螯合性和PDT活性的ALA-HPO杂合衍生物及其制备方法与应用

  摘要：

  本发明提供了一种式(I)或式(II)所示的ALA‑HPO杂合衍生物及其制备方法，以及在制备光动力学治疗药物中的应用；

  公开号：

  CN112062713B
• 作为产物：
  描述：

  氯化苄 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 7.5h， 生成 5-(benzyloxy)-2-(hydroxymethyl)-1-octylpyridin-4(1H)-one
  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

• 具铁螯合性和PDT活性的ALA-HPO杂合衍生物及其制备方法与应用
  申请人：浙江工业大学

  公开号：CN112062713B

  公开（公告）日：2023-03-31

  本发明提供了一种式(I)或式(II)所示的ALA‑HPO杂合衍生物及其制备方法，以及在制备光动力学治疗药物中的应用；
• 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.