3-[2-methyl-3-benzyloxypyridin-4(1H)-one-1-yl]-1-propanol | 95215-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[2-methyl-3-benzyloxypyridin-4(1H)-one-1-yl]-1-propanol
• 英文别名: (3'-hydroxypropyl)-3-benzyloxy-2-methyl-4-pyridinone；3-Benzyloxy-1-(3'-hydroxypropyl)-2-methylpyrid-4-one；1-(3-hydroxypropyl)-2-methyl-3-phenylmethoxypyridin-4-one
• CAS: 95215-84-2
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: XLRVEQKZTMQZHU-UHFFFAOYSA-N

物化性质

• 沸点：
  469.4±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  3-[2-methyl-3-benzyloxypyridin-4(1H)-one-1-yl]-1-propanol 在 palladium on activated charcoal 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 3-(3,4-Dihydroxy-2-methylpyridin-1-ium-1-yl)propyl 4-methylbenzoate;chloride
  参考文献：
  名称：

  Liu, Zu D.; Liu, Ding Y.; Lu, Shu L., Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 5, p. 461 - 470

  摘要：

  DOI：
• 作为产物：
  描述：

  麦芽醇 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 3-[2-methyl-3-benzyloxypyridin-4(1H)-one-1-yl]-1-propanol
  参考文献：
  名称：

  N-取代的2-烷基-3-羟基-4（1H）-吡啶酮的合成，理化性质和生物学评估：具有临床潜力的口服活性铁螯合剂。

  摘要：

  描述了一系列包含螯合部分3-羟基-4（1H）-吡啶酮的新型双齿配体的合成。已经确定了配体的pKa值及其铁（III）配合物的稳定性常数。给出了一种配体和一种铁（III）配合物的晶体结构。报告了配体的分布系数，并且与配体从肝细胞中去除铁的能力有关。描述了3-羟基-4（1H）-吡啶酮对细胞氧化损伤的影响。与目前的铁螯合剂去铁胺-B相比，本研究中描述的许多双齿配体在铁超载小鼠中具有口服活性。

  DOI：

  10.1021/jm00069a002

文献信息

• Synthesis of New Bis(3-hydroxy-4-pyridinone) Ligands as Chelating Agents for Uranyl Complexation
  作者：Bo Jin、Rongzong Zheng、Rufang Peng、Shijin Chu

  DOI：10.3390/molecules21030299

  日期：——

  (13)C-NMR, FT-IR, UV-vis, and mass spectral analyses. The binding abilities of these tetradentate chelators for uranyl ion at pH 7.4 were also determined by UV spectrophotometry in aqueous media. Results showed that the efficiencies of these chelating agents are dependent on the linker length. Ligand 4b is the best chelator and suitable for further studies.

  这项研究中合成了五种新的双（3-羟基-4-吡啶酮）四齿螯合剂。这些四齿螯合剂的结构通过1 H-NMR，（13）C-NMR，FT-IR，UV-vis和质谱分析来表征。还通过在水介质中的紫外分光光度法测定了这些四齿螯合剂在pH 7.4下对铀酰离子的结合能力。结果表明，这些螯合剂的效率取决于接头的长度。配体4b是最好的螯合剂，适合进一步研究。
• Design and synthesis of N-hydroxyalkyl substituted deferiprone: a kind of iron chelating agents for Parkinson's disease chelation therapy strategy
  作者：Qingchun Zhang、Shufan Feng、Yulian Zhao、Bo Jin、Rufang Peng

  DOI：10.1007/s00775-021-01863-x

  日期：2021.6

  drazyl radical scavenging assays indicated that the N-hydroxyalkyl substituted deferiprone also possesses similar radical scavenging ability in comparison to deferiprone. Meanwhile, the Cell Counting Kit-8 assays of neuron-like rat pheochromocytoma cell-line demonstrated that the N-hydroxyalkyl substituted deferiprone exhibits extremely low cytotoxicity and excellent H2O2-induced oxidative stress protection

  分子的血脑屏障（BBB）通透性需要满足利平斯基规则的严格要求，这给合理设计用于帕金森病螯合治疗的高效螯合剂带来了困难。因此，本工作合理设计了使用去铁酮的N-脂肪醇修饰的铁螯合剂。螯合剂不仅满足利平斯基对血脑屏障通透性的规则，而且保证了铁的亲和力。溶液热力学结果表明，N-羟烷基取代去铁酮的pFe 3+值在19.20～19.36之间，与临床去铁酮相当。2,2-diphenyl-1-picrylhydrazyl 自由基清除实验结果表明，N与去铁酮相比，-羟烷基取代的去铁酮还具有类似的自由基清除能力。同时，神经元样大鼠嗜铬细胞瘤细胞系的Cell Counting Kit-8分析表明，N-羟烷基取代的去铁酮表现出极低的细胞毒性和优异的H 2 O 2诱导的氧化应激保护作用。这些结果表明，N-羟烷基取代的去铁酮作为帕金森病螯合治疗策略的螯合剂具有潜在的应用前景。 图形摘要
• Iron-pyridone complexes for anemia
  申请人：National Research Development Corporation

  公开号：US04650793A1

  公开（公告）日：1987-03-17

  Pharmaceutical compositions containing an iron complex of a 3-hydroxypyrid-2-one or 3-hydroxypyrid-4-one in which the hydrogen atom attached to the nitrogen atom is replaced by an aliphatic acyl group, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by one or, except in the case of ionizable groups, more than one substituent selected from aliphatic acyl, alkoxy, aliphatic amine, aliphatic amide, carboxy, aliphatic ester, halogen, hydroxy and sulpho groups and, optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by one of said substituents, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms in the compound is effected only by aliphatic hydrocarbon groups, are of value for the treatment of iron deficiency anemia.

  含有3-羟基吡啶-2-酮或3-羟基吡啶-4-酮的铁络合物的药物组合物，其中氮原子上连接的氢原子被取代为脂肪族酰基团、脂肪族碳氢基团或被选自脂肪族酰基、烷氧基、脂肪族胺、脂肪族酰胺、羧基、脂肪族酯、卤素、羟基和磺酸基中的一个或一个以上取代基的烷基碳氢基团取代，且可选地，其中一个或多个连接到环碳原子的氢原子被取代为上述取代基之一，或被取代为烷氧基、脂肪族酯、卤素或羟基的脂肪族碳氢基团或被取代为烷氧基、脂肪族酯、卤素或羟基的脂肪族碳氢基团取代，但不包括仅由脂肪族碳氢基团取代化合物的价值，用于治疗缺铁性贫血。
• Pharmaceutical compositions
  申请人：National Research Development Corp.

  公开号：US04585780A1

  公开（公告）日：1986-04-29

  Pharmaceutical compositions containing a 3-hydroxypyrid-2-one or 3-hydroxypyrid-4-one in which the hydrogen atom attached to the nitrogen atom is replaced by an aliphatic acyl group, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by one or, except in the case of ionizable groups, more than one substituent selected from aliphatic acyl, alkoxy, aliphatic amine, aliphatic amide, carboxy, aliphatic ester, halogen, hydroxy and sulpho groups and, optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by one of said substituents, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms in the compound is effected only by aliphatic hydrocarbon groups, or a salt thereof containing a physiologically acceptable ion or ions, are of value for removing toxic amounts of metals, particularly iron, from the body.

  含有3-羟基吡啶-2-酮或3-羟基吡啶-4-酮的制剂，其中连接氮原子的氢原子被取代为脂肪族酰基团、脂肪族碳氢基团或被脂肪族碳氢基团取代并带有从脂肪族酰基、烷氧基、脂肪族胺、脂肪族酰胺、羧基、脂肪族酯、卤素、羟基和磺酸基中选择的一个或多个取代基，而且在环碳原子上的一个或多个氢原子被取代为其中一种取代基、脂肪族碳氢基团或被烷氧基、脂肪族酯、卤素或羟基基团取代的脂肪族碳氢基团，但不包括化合物中只通过脂肪族碳氢基团取代氢原子的情况，或其含有生理上可接受的离子的盐，对于从体内去除有毒量的金属，特别是铁，具有价值。
• 3-Hydroxypyrid-4-ones and pharmaceutical compositions
  申请人：BRITISH TECHNOLOGY GROUP LIMITED

  公开号：EP0305646A2

  公开（公告）日：1989-03-08

  Pharmaceutical compositions containing a 3-hydroxypyrid-2-one or 3-hydroxypyrid-4-one in which the hydrogen atom attached to the nitrogen atom is replaced by an aliphatic acyl group, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by one or more substituents selected from aliphatic acyl, aliphatic amide, aliphatic ester, halogen and hydroxy groups and, optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by one of said substituents, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms in the compound is effected only by substituents selected from aliphatic hydrocarbon groups and aliphatic hydrocarbon groups substituted by an alkoxy group or groups, or a physiologically acceptable salt thereof, are of value for removing toxic amounts of metals, particularly iron, from the body.

  含有 3-羟基吡啶-2-酮或 3-羟基吡啶-4-酮的药物组合物，其中与氮原子相连的氢原子被脂族酰基、脂族烃基或被选自脂族酰基、脂族酰胺、脂族酯、卤素和羟基的一个或多个取代基取代，并且可选地，其中与环碳原子相连的一个或多个氢原子被上述取代基之一取代、脂族烃基，或被烷氧基、脂族酯、卤素或羟基取代的脂族烃基，但不包括仅由选自脂族烃基和被一个或多个烷氧基取代的脂族烃基的取代基实现化合物中氢原子的取代的化合物，或其生理上可接受的盐。