1-<(methoxycarbonyl)methyl>-3-hydroxy-2(1H)pyridinone | 95215-71-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-<(methoxycarbonyl)methyl>-3-hydroxy-2(1H)pyridinone
• 英文别名: 1-[(methoxycarbonyl)methyl]-3-hydroxy-2-(1H)-pyridinone；1-[(methoxycarbonyl)methyl]-3-hydroxy-2-(1H)-pyridone；N-[(methoxycarbonyl)methyl]-3-hydroxy-2-(1H)-pyridone；3-hydroxy-1-methoxycarbonylmethylpyrid-2-one；Methyl 2-(3-hydroxy-2-oxopyridin-1-yl)acetate
• CAS: 95215-71-7
• 化学式: C₈H₉NO₄
• 分子量: 183.164
• InChiKey: BCQXLOJYGPSEER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<(methoxycarbonyl)methyl>-3-hydroxy-2(1H)pyridinone 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 生成 2-[3-(Methoxymethoxy)-2-oxopyridin-1-yl]acetic acid
  参考文献：
  名称：

  新型六齿3-羟基-2（1 H）吡啶酮配体的合成，理化性质和铁（III）螯合特性

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(98)01091-6
• 作为产物：
  描述：

  1-carboxymethyl-3-hydroxy-2(1H)pyridinone 以 methanolic hydrochloric acid 为溶剂， 以60%的产率得到1-<(methoxycarbonyl)methyl>-3-hydroxy-2(1H)pyridinone
  参考文献：
  名称：

  Iron-pyridone complexes for anemia

  摘要：

  含有3-羟基吡啶-2-酮或3-羟基吡啶-4-酮的铁配合物的制药组合物，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，或者被脂肪烃基取代，该脂肪烃基被选自脂肪酰基、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，并且可选地，其中连接到环碳原子的一个或多个氢原子被上述取代物之一取代，被烷氧基、脂肪酯基、卤素或羟基取代的脂肪烃基取代，但不包括只通过脂肪烃基进行氢原子取代的化合物，对于治疗缺铁性贫血具有价值。

  公开号：

  US04650793A1

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。
• Synthesis and characterisation of cis-dioxomolybdenum(vi) complexes of N-substituted 3-hydroxy-2-pyridinonesElectronic supplementary information (ESI) available: ORTEP plot and structural details of [MoO2(Lb)2]. See http://www.rsc.org/suppdata/dt/b4/b407221a/
  作者：Emma J. Brown、Adrian C. Whitwood、Paul H. Walton、Anne-K. Duhme-Klair

  DOI：10.1039/b407221a

  日期：——

  The butoxy- and methoxy-derivatives (HLc, and HLb, respectively) of 1-[(ethoxycarbonyl)methyl]-3-hydroxy-2-(1H)-pyridinone, HLa, were synthesized by transesterification and the mononuclear complexes [MoO2(La–c)2] were obtained by the reaction of the ligands with molybdenyl acetylacetonate. The three complexes were fully characterized by 1H and 13C NMR spectroscopy, mass spectrometry and elemental analyses. A variable temperature NMR study showed that the N-substituents do not have a significant influence on the racemisation process of the complexes. The comparison of the crystal structure of [MoO2(Lb)2] with [MoO2(La)2] confirmed that an additional methylene group does not affect the immediate coordination environment of the molybdenum centre. The methoxy-derivative HLb was also found to produce a dinuclear complex of composition [MoO2(Lb)O}2], the structure of which was determined by X-ray diffraction.

  通过酯交换反应合成了 1-[（乙氧基羰基）甲基]-3-羟基-2-(1H)-吡啶酮 HLa 的丁氧基和甲氧基衍生物（分别为 HLc 和 HLb），并通过配体与乙酰丙酮钼酸酯反应得到了单核络合物 [ (La-c)2]。通过 1H 和 13C NMR 光谱、质谱和元素分析，对这三种配合物进行了全面表征。变温核磁共振研究表明，N-取代基对配合物的消旋化过程没有显著影响。对 [ (Lb)2] 和 [ (La)2] 晶体结构的比较证实，额外的亚甲基不会影响钼中心的直接配位环境。此外，还发现甲氧基衍生物 HLb 产生了一种成分为 [MoO2(Lb)O}2] 的双核配合物，其结构已通过 X 射线衍射确定。
• Is the Reactivity of M(II)−Arene Complexes of 3-Hydroxy-2(1<i>H</i>)-pyridones to Biomolecules the Anticancer Activity Determining Parameter?
  作者：Muhammad Hanif、Helena Henke、Samuel M. Meier、Sanela Martic、Mahmoud Labib、Wolfgang Kandioller、Michael A. Jakupec、Vladimir B. Arion、Heinz-Bernhard Kraatz、Bernhard K. Keppler、Christian G. Hartinger

  DOI：10.1021/ic1009785

  日期：2010.9.6

  the reactions with the model proteins ubiquitin and cytochrome c, yielding mainly [protein + M(η6-p-cymene)] adducts (M = Ru, Os). Notably the ligand cleavage of the Os derivative was significantly slower than of its Ru analogue, which could explain its higher activity in in vitro anticancer assays. Furthermore, the reaction of the compounds to 5′-GMP was characterized and coordination to the N7 of

  羟基吡啶酮是有机金属抗癌剂合成的多功能配体，具有良好的药理学性质。在本文中，我们报道了具有烷氧基羰基甲基-3-羟基-2-吡啶酮配体的Ru II-和Os II-芳烃配合物的制备，作用方式和体外抗癌活性。水解和与氨基酸的结合迅速进行，如NMR光谱和ESI质谱所表征。然而，与氨基酸的反应导致吡啶酮配体从金属中心裂解，因为氨基酸充当多齿配体。与遍在蛋白模型和细胞色素c在反应期间，也观察到类似的行为，产生主要[蛋白质+ M（η 6 - p-cymene）加合物（M = Ru，Os）。值得注意的是，Os衍生物的配体裂解比其Ru类似物的裂解要慢得多，这可以解释其在体外抗癌试验中的较高活性。此外，表征了化合物与5'-GMP的反应，并通过1 H NMR光谱和X射线衍射分析证明了与鸟嘌呤部分的N 7的配位。CDK2 / Cyclin A蛋白激酶抑制研究揭示了Ru和Os复合物的有效活性。
• 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。
• HIDER, R. C.;KONTOGHIORGHES, G.;SILVER, J.;STOCKHAM, M. A.
  作者：HIDER, R. C.、KONTOGHIORGHES, G.、SILVER, J.、STOCKHAM, M. A.

  DOI：——

  日期：——