3-Benzyloxy-1,6-dimethyl-2-propyl-1H-pyridin-4-one | 1026068-71-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Benzyloxy-1,6-dimethyl-2-propyl-1H-pyridin-4-one
• 英文别名: 1,6-Dimethyl-3-phenylmethoxy-2-propylpyridin-4-one
• CAS: 1026068-71-2
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: ULGRUNSYTFMFPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Benzyloxy-1,6-dimethyl-2-propyl-1H-pyridin-4-one 在 5percent Pd/C 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 1,6-dimethyl-2-propyl-3-hydroxypyridin-4(1H)-one hydrochloride
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Novel 2-Substituted 3-Hydroxypyridin-4-ones:  Structure−Activity Investigation of Metalloenzyme Inhibition by Iron Chelators

  摘要：

  A range of novel 3-hydroxypyridin-4-ones with different R(2) substitutents has been synthesized for the investigation of the structure-activity relationship between the chemical nature of the ligand and the inhibitory activity of the iron-containing metalloenzyme 5-lipoxygenase. Results indicate that the molecular dimensions, together with the lipophilicity, have a critical impact on the ability of this class of chelator to inhibit 5-lipoxygenase. Hydrophilic ligands with a bulky R(2) substitutent tend to be weak inhibitors; thus 1,6-dimethyl-2-(4'-N-n-propylsuccinamido)methyl-3-hydroxypyridin-4(1H)-one (22b) which has the largest R(2) substitutent only caused 2% inhibition of the enzyme activity after 30 min incubation at 110 muM IBE (iron-binding equivalents), as compared with deferiprone which caused 40% inhibition of the enzyme activity, under the same conditions.

  DOI：

  10.1021/jm010817i
• 作为产物：
  描述：

  2-propyl-6-methyl-3-hydroxy-4-pyrone 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 18.0h， 生成 3-Benzyloxy-1,6-dimethyl-2-propyl-1H-pyridin-4-one
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Novel 2-Substituted 3-Hydroxypyridin-4-ones:  Structure−Activity Investigation of Metalloenzyme Inhibition by Iron Chelators

  摘要：

  A range of novel 3-hydroxypyridin-4-ones with different R(2) substitutents has been synthesized for the investigation of the structure-activity relationship between the chemical nature of the ligand and the inhibitory activity of the iron-containing metalloenzyme 5-lipoxygenase. Results indicate that the molecular dimensions, together with the lipophilicity, have a critical impact on the ability of this class of chelator to inhibit 5-lipoxygenase. Hydrophilic ligands with a bulky R(2) substitutent tend to be weak inhibitors; thus 1,6-dimethyl-2-(4'-N-n-propylsuccinamido)methyl-3-hydroxypyridin-4(1H)-one (22b) which has the largest R(2) substitutent only caused 2% inhibition of the enzyme activity after 30 min incubation at 110 muM IBE (iron-binding equivalents), as compared with deferiprone which caused 40% inhibition of the enzyme activity, under the same conditions.

  DOI：

  10.1021/jm010817i