5-羟基-2-(羟基甲基)-1-甲基-4(1H)-吡啶酮 | 70033-59-9

• 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
• 中文名称: 5-羟基-2-(羟基甲基)-1-甲基-4(1H)-吡啶酮
• 英文名称: 6-hydroxymethyl-3-hydroxy-1-methyl-4-pyridinone
• 英文别名: 5-hydroxy-2-hydroxymethyl-1-methyl-4(1H)-pyridinone；3-hydroxy-6-hydroxymethyl-1-methyl-4-pyridinone；5-hydroxy-2-hydroxymethyl-1-methyl-4-pyridone；3-hydroxy-6-hydroxymethyl-1-methylpyrid-4-one；5-hydroxy-2-hydroxymethyl-1-methyl-1H-pyridin-4-one；5-Hydroxy-2-hydroxymethyl-1-methyl-1H-pyridin-4-on；5-Hydroxy-2-hydroxymethyl-1-methylpyrid-4-one；5-hydroxy-2-(hydroxymethyl)-1-methylpyridin-4-one
• CAS: 70033-59-9
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: XATJWQRIODISIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-羟基-2-(羟基甲基)-1-甲基-4(1H)-吡啶酮 、 乙胺盐酸盐 在 盐酸甲胺 作用下， 生成 1-乙基-5-羟基-2-(羟甲基)吡啶-4-酮
  参考文献：
  名称：

  Pharmaceutical compositions

  摘要：

  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。

  公开号：

  US04585780A1
• 作为产物：
  描述：

  曲酸 、 甲胺 在 水 、 盐酸 作用下， 以 水 为溶剂， 反应 16.0h， 生成 5-羟基-2-(羟基甲基)-1-甲基-4(1H)-吡啶酮
  参考文献：
  名称：

  Vanadium complexes and derivatives thereof and methods related thereto

  摘要：

  提供了有机钒配合物，更具体地说是羟基氧钒(V)、&mgr;-氧代二聚氧钒(V)和顺式二氧代氧钒(V)配合物。这些配合物可以制成药物组合物。这些配合物和/或组合物可以用于治疗多种疾病状态，包括用作抗增殖和/或抗转移剂，治疗耐药性肿瘤和/或减少肿瘤转移能力的方法，以及治疗糖尿病、关节炎、多发性硬化症、涉及身体通道的疾病和自身免疫性疾病，包括但不限于银屑病和狼疮。

  公开号：

  US06232340B1

文献信息

• [EN] COMPOSITIONS AND METHODS FOR INHIBITING INFLUENZA RNA POLYMERASE PA ENDONUCLEASE<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR INHIBER L'ENDONUCLÉASE DE LA PA DE L'ARN POLYMÉRASE DE LA GRIPPE
  申请人：UNIV CALIFORNIA

  公开号：WO2017156194A1

  公开（公告）日：2017-09-14

  There are provided inter alia metalloenzyme inhibitors, such as inhibitors of influenza A RNA dependent RNA polymerase PA subunit endonuclease, and methods of synthesis and use of the same.

  其中提供了金属酶抑制剂，例如流感A病毒RNA依赖性RNA聚合酶PA亚基内切酶的抑制剂，以及其合成和使用方法。
• Synthesis, characterization, and biological relevance of hydroxypyrone and hydroxypyridinone complexes of molybdenum
  作者：Sarah J Lord、Noah A Epstein、Robert L Paddock、Christopher M Vogels、Tracy L Hennigar、Michael J Zaworotko、Nicholas J Taylor、William R Driedzic、Tom L Broderick、Stephen A Westcott

  DOI：10.1139/v99-111

  日期：1999.7.1

  We have prepared a number of complexes of the type cis-MoO₂L₂ where L represents a hydroxypyronato or hydroxypyridinonato ligand. Both the maltol (3-hydroxy-2-methyl-4-pyrone, Hma) and kojic acid (5-hydroxy-2-hydroxymethyl-4-pyrone, Hka) complexes, cis-MoO₂(ma)₂ (1) and cis-MoO₂(ka)₂ (2), have been characterized by X-ray diffraction studies. The pyrone ligands are bound to molybdenum in a cis bidentate fashion via the deprotonated hydroxyl groups and the ketone moieties. Crystals of 1 are orthorhombic, a = 12.107 (1), b = 8.6169 (8), c = 16.472 (1) Å, Z = 4, space group Pca2₁, and those of 2 are monoclinic, a = 8.4591 (5), b = 16.3453 (10), c = 10.2954 (7) Å, β = 103.0320 (10)°, Z = 4, space group P2₁/c. Hydroxypyridinone molybdenum complexes have been prepared for both maltol and kojic acid derivatives with the substituents Me, n-Pr, CH₂Ph, Ph at the ring nitrogen. Crystals of the 3-hydroxy-2-methyl-1-phenyl-4-pyridinone (Hppp) derivative, MoO₂(ppp)₂ (9), are monoclinic, a = 10.9476 (6), b = 13.5353 (9), c = 17.4877 (10) Å, β = 93.465 (4)°, Z = 4, space group P2₁/n. Initial investigations into the effects molybdenum compounds have on diabetic hearts are presented. Both Na₂MoO₄ (used as a control) and 1 were effective in lowering blood glucose and free fatty acid levels. Diabetic rats treated with molybdate showed significant improvements in postischemic cardiac function.Key words: molybdenum, hydroxypyrones, hydroxypyridinones, heart function.

  我们已经准备了一系列cis-MoO₂L₂类型的配合物，其中L代表羟基吡啶酮或羟基吡啶酮配体。麦芽酮（3-羟基-2-甲基-4-吡喃酮，Hma）和曲酸（5-羟基-2-羟甲基-4-吡喃酮，Hka）配合物，cis-MoO₂(ma)₂（1）和cis-MoO₂(ka)₂（2），已经通过X射线衍射研究进行了表征。吡喃酮配体以顺式双齿方式通过去质子羟基和酮基与钼结合。1的晶体为正交晶系，a = 12.107（1），b = 8.6169（8），c = 16.472（1）埃，Z = 4，空间群Pca2₁，而2的晶体为单斜晶系，a = 8.4591（5），b = 16.3453（10），c = 10.2954（7）埃，β = 103.0320（10）°，Z = 4，空间群P2₁/c。已经为麦芽酮和曲酸衍生物制备了羟基吡啶酮钼配合物，其在环氮原子处具有Me、n-Pr、CH₂Ph、Ph等取代基。3-羟基-2-甲基-1-苯基-4-吡啶酮（Hppp）衍生物MoO₂(ppp)₂（9）的晶体为单斜晶系，a = 10.9476（6），b = 13.5353（9），c = 17.4877（10）埃，β = 93.465（4）°，Z = 4，空间群P2₁/n。首次研究了钼化合物对糖尿病心脏的影响。钼酸钠（用作对照）和1在降低血糖和游离脂肪酸水平方面均有效。接受钼酸盐治疗的糖尿病大鼠在缺血后心脏功能方面表现出显著改善。关键词：钼、羟基吡喃酮、羟基吡啶酮、心脏功能。
• Directed aminomethylation of 3-hydroxy-2(1H)-pyridinones and 3-hydroxy-4(1H)-pyridinones: Synthesis of iso-deferiprone
  作者：Manojbhai K. Patel、Raymond Fox、Paul D. Taylor

  DOI：10.1016/0040-4020(95)01016-5

  日期：1996.1

  aminomethylation of N-unsubstituted 3-hydroxy-2-(1H)-pyridinones and 3-hydroxy-4(1H)-pyridinones, under Mannich reaction conditions, is directed by the hydroxyl group when this is unprotected and by the kelo group when the hydroxyl is protected as an ether. This offers a convenient route to a variety of Mannich base synthons useful in the synthesis of derivatives of these clinically important, bidentate

  在曼尼希反应条件下，N-未取代的3-羟基-2-（1H）-吡啶酮和3-羟基-4（1H）-吡啶酮的氨基甲基化位点由未保护的羟基和开环组成当羟基被保护为醚时的基团。这提供了通往各种曼尼希碱基合成子的便捷途径，这些合成子可用于合成这些临床上重要的双齿金属离子螯合剂的衍生物。这可以通过3-羟基-2-（1H）-吡啶酮，3-甲氧基-2（1H）-吡啶酮，2-羟基甲基-5-羟基-4（1H）吡啶酮和3-苄氧基-2-甲基的反应来举例说明。-4（1H）-吡啶酮。
• 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。