1,6-dimethyl-2-(4'-N-n-propylsuccinamido)methyl-3-benzyloxypyridin-4(1H)-one | 401792-12-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-dimethyl-2-(4'-N-n-propylsuccinamido)methyl-3-benzyloxypyridin-4(1H)-one
• 英文别名: N'-[(1,6-dimethyl-4-oxo-3-phenylmethoxypyridin-2-yl)methyl]-N-propylbutanediamide
• CAS: 401792-12-9
• 化学式: C₂₂H₂₉N₃O₄
• 分子量: 399.49
• InChiKey: NNDSIXDYAAYFSY-UHFFFAOYSA-N

物化性质

• 熔点：
  124-127 °C
• 沸点：
  680.9±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,6-dimethyl-2-(4'-N-n-propylsuccinamido)methyl-3-benzyloxypyridin-4(1H)-one 在 5percent Pd/C 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-Hydroxypyridin-4-one,N-methyl-2-(N'-propylsucc
  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：

  曲酸 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 对甲苯磺酸 、 三苯基膦 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 52.0h， 生成 1,6-dimethyl-2-(4'-N-n-propylsuccinamido)methyl-3-benzyloxypyridin-4(1H)-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

文献信息

• Design, Synthesis, and Evaluation of Novel 2-Substituted 3-Hydroxypyridin-4-ones:  Structure−Activity Investigation of Metalloenzyme Inhibition by Iron Chelators
  作者：Zu D. Liu、Reem Kayyali、Robert C. Hider、John B. Porter、Anthony E. Theobald

  DOI：10.1021/jm010817i

  日期：2002.1.1

  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.