1-<(propylcarbamoyl)methyl>-3-hydroxy-2(1H)pyridinone | 95215-79-5

• 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-<(propylcarbamoyl)methyl>-3-hydroxy-2(1H)pyridinone
• 英文别名: 2-(3-hydroxy-2-oxopyridin-1(2H)-yl)-N-propylacetamide；3-hydroxy-1-(N-propylcarbamoylmethyl)-pyrid-2-one；3-Hydroxy-1-[propylcarbamoylmethyl]-2-pyridinone；2-(3-hydroxy-2-oxopyridin-1-yl)-N-propylacetamide
• CAS: 95215-79-5
• 化学式: C₁₀H₁₄N₂O₃
• 分子量: 210.233
• InChiKey: WOKYKDOQLDUXCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 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：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-<(propylcarbamoyl)methyl>-3-hydroxy-2(1H)pyridinone 生成 2-(3-hydroxy-2-oxopyridin-1-yl)-N-propylacetamide;trichloroiron
  参考文献：
  名称：

  HIDER, R. C.;KONTOGHIORGHES, G.;SILVER, J.;STOCKHAM, M. A.

  摘要：

  DOI：
• 作为产物：
  描述：

  吡啶-2,3-二醇 在 10% Pd/C 、 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、1.5 MPa 条件下， 反应 42.33h， 生成 1-<(propylcarbamoyl)methyl>-3-hydroxy-2(1H)pyridinone
  参考文献：
  名称：

  吡啶-2-和-4-酮的有机金属钌和锇化合物作为潜在的抗癌剂

  摘要：

  有机金属 RuII 化合物是研究最广泛的抗癌剂之一。用生物分子衍生的配体功能化金属中心已被证明是提高金属基化疗药物抗增殖活性的一种有前景的策略。本文描述了一系列新型 3-羟基吡啶-2-one 衍生配体及其 MII(η6-p-cymene) 半夹心配合物 (M=Ru, Os) 的合成。通过1D-和2D-NMR光谱以及元素分析对化合物进行表征。

  DOI：

  10.1002/cbdv.201200005

文献信息

• 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-酮的药物组合物，其中连接到氮原子的氢原子被脂肪酰基、脂肪烃基或被脂肪烃基取代，并且被脂肪酰基、烷氧基、脂肪胺基、脂肪酰胺基、羧基、脂肪酯基、卤素、羟基和磺酸基中的一个或一个以上的取代基取代，除非是可电离的基团，可选地，其中连接到环碳原子的一个或多个氢原子被上述取代基之一取代，或者被烷氧基、脂肪酯基、卤素或羟基取代的脂肪烃基取代，但不包括化合物，其中所述取代氢原子的取代仅由脂肪烃基完成，或者其盐，含有生理上可接受的离子，对于从体内去除有毒金属，特别是铁，具有价值。
• Novel 3-hydroxy-2(1H)-pyridinones. Synthesis, iron(III)-chelating properties and biological activity
  作者：Michael Streater、Paul D. Taylor、Robert C. Hider、John Porter

  DOI：10.1021/jm00168a033

  日期：1990.6

  The synthesis of a range of novel bidentate and hexadentate ligands containing the chelating moiety 3-hydroxy-2(1H)-pyridinone is described. The pKa values of the ligands and the stability constants of their iron(III) complexes have been determined. The stability constant of the iron(III) complex of one of the hexadentate ligands is comparable to that of desferrioxamine B. The distribution coefficients

  描述了一系列包含螯合部分3-羟基-2（1H）-吡啶酮的新颖的二齿和六齿配体的合成。已经确定了配体的pKa值及其铁（III）配合物的稳定性常数。六齿配体之一的铁（III）配合物的稳定性常数与去铁胺B相当。配体及其铁（III）配合物的分布系数也被确定。新型六齿化合物之一已显示出可显着增强肝细胞和铁超载小鼠的铁（III）排泄。
• Synthesis, physico-chemical and iron(III)-chelating properties of novel hexadentate 3-hydroxy-2(1H)pyridinone ligands
  作者：Bijaya L Rai、Hicham Khodr、Robert C Hider

  DOI：10.1016/s0040-4020(98)01091-6

  日期：1999.1

  Synthesis of hexadentate ligands via the in situ formation of 1-hydroxy benzotriazolyl active ester in the presence of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, TBTU as a coupling agent is described. The pKa values and distribution coefficient values (1-octanol/water) of the ligands and the stability constants of their iron(III) complexes are reported.

  六齿配位体的合成通过在原位在2-（1的存在形成1-羟基苯并三唑活性酯的ħ苯并三唑-1-基）-1,1,3,3-四甲基脲四氟硼酸盐，TBTU作为偶联剂是描述。报道了配体的pKa值和分布系数值（1-辛醇/水）及其铁（III）配合物的稳定性常数。
• Iron III complexes of hydroxypyridones, and their pharmaceutical compositions
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0120670A1

  公开（公告）日：1984-10-03

  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 ionisable 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 anaemia.

  含有 3-羟基吡啶-2-酮或 3-羟基吡啶-4-酮铁络合物的药物组合物，其中与氮原子相连的氢原子被脂肪族酰基、脂肪族烃基或被一个或一个以上取代基取代的脂肪族烃基所取代（可电离基团除外），取代基选自脂肪族酰基、烷氧基、脂肪族胺、脂肪族酰胺、羧基、脂肪族酯、卤素、在可离子化基团的情况下，一个以上选自脂肪族酰基、烷氧基、脂肪族酰胺、羧基、脂肪族酯、卤素、羟基和磺基的取代基，以及环碳原子上的一个或多个氢原子被上述取代基、脂肪族烃基或被烷氧基、脂肪族酯、卤素或羟基取代的脂肪族烃基取代，但不包括化合物中的氢原子仅被脂肪族烃基取代的化合物，这些化合物具有治疗缺铁性贫血的价值。
• Hydroxypyridones, and their pharmaceutical compositions
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0120669A2

  公开（公告）日：1984-10-03

  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 ionisable 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 saltthereof 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、脂族烃基取代、或被一个或一个以上取代基取代的脂肪族烃基，这些取代基选自脂肪族酰基、烷氧基、脂肪族胺、脂肪族酰胺、羧基、脂肪族酯、卤素、羟基和亚砜基，可选的情况除外、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、脂肪族烃基或被烷氧基、脂肪族酯、卤素或羟基取代的脂肪族烃基所取代，但不包括化合物中的氢原子仅被脂肪族烃基取代的化合物，或含有生理上可接受的一种或多种离子的盐。