1-(3'-carboxypropyl)-2-methyl-3-hydroxy-4(1H)-pyridinone hydrochloride | 143573-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(3'-carboxypropyl)-2-methyl-3-hydroxy-4(1H)-pyridinone hydrochloride
• 英文别名: 4-(3-Hydroxy-2-methyl-4-oxopyridin-1-yl)butanoic acid;hydrochloride；4-(3-hydroxy-2-methyl-4-oxopyridin-1-yl)butanoic acid;hydrochloride
• CAS: 143573-06-2
• 化学式: C₁₀H₁₃NO₄*ClH
• 分子量: 247.678
• InChiKey: PYRGQGNAGZYYPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(3'-carboxypropyl)-2-methyl-3-(benzyloxy)-4(1H)-pyridinone hydrochloride 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 1-(3'-carboxypropyl)-2-methyl-3-hydroxy-4(1H)-pyridinone hydrochloride
  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

• 3-hydroxypyridin-4-one derivatives as pharmaceutical compositions
  申请人：BRITISH TECHNOLOGY GROUP LTD

  公开号：EP0494754A1

  公开（公告）日：1992-07-15

  3-Hydroxypyridin-4-ones of formula (I) in which R₁ is selected from hydrogen, C₁₋₃ aliphatic hydrocarbon groups, 2-hydroxyethyl, C₁₋₄ aliphatic hydrocarbon groups substituted by a single carboxy, sulpho, sulphamoyl or N-methyl or N-ethyl sulphamoyl group, and an ethyl group substituted at the 1-or 2-position by a carboxy, sulpho, sulphamoyl or N-methyl or N-ethyl sulphamoyl group and at the 2-position by a hydroxy group, and R₂, R₃ and R₄ are each separately selected from hydrogen, C₁₋₃ aliphatic hydrocarbon groups, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-methoxymethyl, C₁₋₄ aliphatic hydrocarbon groups substituted by a single carboxy, sulpho, sulphamoyl or N-methyl or N-ethyl sulphamoyl group, and an ethyl group substituted at the 1-or 2-position by a carboxy, sulpho, sulphamoyl or N-methyl or N-ethyl sulphamoyl group and at the 2-position by a hydroxy group, but with the provisos firstly that one of R₁ to R₄ is a C₁₋₄ aliphatic hydrocarbon group substituted by a single carboxy, sulpho, sulphamoyl or N-methyl or N-ethyl sulphamoyl group, or an ethyl group substituted at the 1- or 2-position by a carboxy, sulpho, sulphamoyl or N-methyl or N-ethyl sulphamoyl group and at the 2-position by a hydroxy group, secondly that either R₂ or R₃ is a group other than hydrogen and thirdly that the total number of atoms other than hydrogen present in R₁ to R₄ is no more than eight, the compound optionally being in the form of a physiologically acceptable salt and/or pro-drug thereof, are of value for the treatment of conditions caused by iron dependent parasites, particularly malaria.

  式(I)中，3-羟基吡啶-4-酮，其中R₁选自氢，C₁₋₃脂肪烃基，2-羟乙基，C₁₋₄脂肪烃基，被单个羧基，磺酰基，磺酰胺基或N-甲基或N-乙基磺酰胺基取代，以及在1-或2-位置被羧基，磺酰基，磺酰胺基或N-甲基或N-乙基磺酰胺基取代的乙基基团，在2-位置被羟基取代；R₂，R₃和R₄各自单独选自氢，C₁₋₃脂肪烃基，羟甲基，1-羟基乙基，2-羟基乙基，2-甲氧基甲基，C₁₋₄脂肪烃基，被单个羧基，磺酰基，磺酰胺基或N-甲基或N-乙基磺酰胺基取代，以及在1-或2-位置被羧基，磺酰基，磺酰胺基或N-甲基或N-乙基磺酰胺基取代的乙基基团，在2-位置被羟基取代，但前提是首先R₁至R₄中有一个是被单个羧基，磺酰基，磺酰胺基或N-甲基或N-乙基磺酰胺基取代的C₁₋₄脂肪烃基，或在1-或2-位置被羧基，磺酰基，磺酰胺基或N-甲基或N-乙基磺酰胺基取代的乙基基团，在2-位置被羟基取代；其次，R₂或R₃为除氢之外的基团；第三，除氢之外的原子总数不超过8个。该化合物可选为生理上可接受的盐和/或前药形式，对于治疗由铁依赖性寄生虫引起的疾病特别是疟疾具有价值。
• Synthesis, physicochemical properties, and biological evaluation of N-substituted 2-alkyl-3-hydroxy-4(1H)-pyridinones: orally active iron chelators with clinical potential
  作者：Paul S. Dobbin、Robert C. Hider、Adrian D. Hall、Paul D. Taylor、Patience Sarpong、John B. Porter、Gaoyi Xiao、Dick van der Helm

  DOI：10.1021/jm00069a002

  日期：1993.8

  The synthesis of a range of novel bidentate ligands containing the chelating moiety 3-hydroxy-4(1H)-pyridinone is described. The pKa values of the ligands and the stability constants of their iron(III) complexes have been determined. The crystal structures of one of the ligands and one of the iron(III) complexes are presented. The distribution coefficients of the ligands are reported and are related

  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。