1-己基-3-羟基-2-甲基吡啶-4-酮 | 30652-18-7

• 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: 1-己基-3-羟基-2-甲基吡啶-4-酮
• 英文名称: 1-Hexyl-3-hydroxy-2-methylpyrid-4-one
• 英文别名: 1-hexyl-3-hydroxy-2-methyl-4(1H)-pyridinone；3-hydroxy-2-methyl-1-hexyl-4-pyridinone；CP25；4(1H)-Pyridinone, 1-hexyl-3-hydroxy-2-methyl-；1-hexyl-3-hydroxy-2-methylpyridin-4-one
• CAS: 30652-18-7
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: UJMBXXIGVFMNDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-己基-3-羟基-2-甲基吡啶-4-酮 、 copper(II) nitrate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.17h， 生成 bis(3-hydroxy-2-methyl-1-hexyl-4-pyridinonato)copper (II)
  参考文献：
  名称：

  独特的EPR信号有助于理解双-（3-羟基-4-吡啶并萘并）铜（ii）配合物对疏水环境的亲和力†

  摘要：

  在这项工作中，我们报告了一组具有可变亲脂性的3-羟基-4-吡啶酮铜（II）配合物的合成和表征。EPR光谱用于表征溶液中铜（II）配合物的结构，并作为了解溶剂相互作用的工具。在不同溶剂中记录的[CuL 2 ]配合物溶液的EPR光谱显示存在两种铜，其比例取决于溶剂的性质。研究纯溶剂甲醇，二甲基亚砜，二氯甲烷及其与甲苯的50％（v / v）混合物中的EPR光谱可以表征两种类型的铜信号（g zz = 2.30和g zz= 2.26），其自旋哈密顿参数与溶剂化和非溶剂化的方平面铜（II）配合物一致。关于配体和配合物的潜在生物应用，以及对水-膜界面中分配特性的深入了解，在水饱和的辛醇，pH = 7.4的水溶液和脂质体悬浮液中也获得了代表三种化合物的EPR光谱。不同的亲脂性平衡。对脂质体中获得的EPR光谱进行分析，可以确定复合物在水相和脂质相中的位置。鉴于这项工作的结果，我们提出了使用EPR光谱法评估铜

  DOI：

  10.1039/c4dt00642a
• 作为产物：
  描述：

  麦芽醇 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 92.0~105.0 ℃ 、400.01 kPa 条件下， 反应 44.0h， 生成 1-己基-3-羟基-2-甲基吡啶-4-酮
  参考文献：
  名称：

  Synthesis, Antiplasmodial Activity, and β-Hematin Inhibition of Hydroxypyridone–Chloroquine Hybrids

  摘要：

  A series of noncytotoxic 4-aminoquinoline-3-hydroxypyridin-4-one hybrids were synthesized on the basis of a synergistic in vitro combination of a precursor N-alkyl-3-hydroxypyridin-4-one with chloroquine (CQ) and tested in vitro against CO resistant (K1 and W2). an sensitive (3D7) strains of Plasmodium falciparum. In vitro antiplasmodial activity of the precursors was negated by blocking the chelator moiety Via complexation with gallium(III) or benzyl protection. None of the precursors inhibited beta-hematin formation. Most hybrids were more potent inhibitors of beta-hematin formation than CQ and a correlation between antiplasmodial activity and inhibition of beta-hematin formation was observed. Potent hybrids against K1, 3D7, and W2, respectively, were 8c (0.13, 0.004, and 0.1 mu M); 8d (0.08, 0.01, and 0.02 mu M); and 7g (0.07, 0.03, and 0.08 mu M).

  DOI：

  10.1021/ml4001084

文献信息

• In vitro studies of 3-hydroxy-4-pyridinones and their glycosylated derivatives as potential agents for Alzheimer's disease
  作者：David E. Green、Meryn L. Bowen、Lauren E. Scott、Tim Storr、Michael Merkel、Karin Böhmerle、Katherine H. Thompson、Brian O. Patrick、Harvey J. Schugar、Chris Orvig

  DOI：10.1039/b918439b

  日期：——

  Glycosides of 3-hydroxy-4-pyridinones were synthesized and characterized by mass spectrometry, elemental analysis, 1H and 13C NMR spectroscopy, and in one case by X-ray crystallography. The Cu2+ complex of a novel 3-hydroxy-4-pyridinone was synthesized and characterized by IR and X-ray crystallography, showing the ability of these compounds to chelate potentially toxic metal ions. An MTT cytotoxicity assay of a selected glycosylated compound showed a relatively low toxicity of IC50 = 570 ± 90 μM in a human breast cancer cell line. The pyridinone glycosides could be cleaved by a broad specificity beta-glycosidase, Agrobacterium sp.β-glucosidase, and for one compound kcat and Km were determined to be 19.8 s−1 and 1.52 mM, respectively. Trolox Equivalent Antioxidant Capacity (TEAC) values were determined for the free pyridinones, indicating the good antioxidant properties of these compounds. Metal-Aβ1-40 aggregates with zinc and copper were resolubilized by the non-glycosylated pyridinone ligands.

  3-羟基-4-吡啶酮的糖苷被合成并通过质谱、元素分析、1H和13C核磁共振波谱进行表征，其中一例通过X射线晶体学进行表征。合成并表征了一种新型3-羟基-4-吡啶酮的Cu2+配合物，通过IR和X射线晶体学表明这些化合物具有潜在的螯合有毒金属离子的能力。对选定的糖基化化合物进行的MTT细胞毒性测定显示，在人乳腺癌细胞系中具有相对较低的毒性，IC50 = 570 ± 90 μM。吡啶酮糖苷可以通过广特异性β-糖苷酶，即根癌农杆菌β-葡糖苷酶分解，对于一种化合物，kcat和Km分别为19.8 s−1和1.52 mM。测定了自由吡啶酮的Trolox等效抗氧化能力（TEAC）值，表明这些化合物具有良好的抗氧化性能。非糖基化的吡啶酮配体可以解溶锌和铜的金属-Aβ1-40聚集体。
• Inhibitor development for 4-hydroxyphenylpyruvate dioxygenase, employing tyrosinemia 1 as a model for human diseases mediated by 2-oxoacid utilizing dioxygenases
  申请人：Hanauske-Abel M. Hartmut

  公开号：US20050288187A1

  公开（公告）日：2005-12-29

  The present invention is directed to a method of inhibiting 4-hydroxyphenylpyruvate dioxygenase in a living system by administering to the living system an effective amount of a compound of formulas I or II or III or derivatives thereof as follows: R 1 , R 2 , R 3 , and R 4 each individually represent a hydrogen, an alkyl, alkenyl, or alkoxy group containing 1 to about 8 carbon atoms, an aryl, aralkyl, or cycloalkyl group containing about 5 to 12 carbon atoms, or a carboalkoxy or carbamyl group containing up to 8 carbon atoms, or a peptide or peptidomimetic moiety containing 10 to about 30 carbon atoms under conditions effective to inhibit 4-hydroxyphenylpyruvate dioxygenase in the living system. These compounds are also useful in carrying out a method of treating a patient and a method of regulating plant growth.

  本发明涉及通过向生物体内投与式I或II或III或其衍生物的有效量来抑制生物体内4-羟基苯丙酮酸双氧酶的方法，其中：R1，R2，R3和R4分别表示氢，含1至约8个碳原子的烷基，烯基或烷氧基，含约5至12个碳原子的芳基，芳基烷基或环烷基，含多达8个碳原子的羧基烷氧基或氨基甲酰基，或含有10至约30个碳原子的肽或类肽基团，在有效条件下抑制生物体内的4-羟基苯丙酮酸双氧酶。这些化合物还可用于进行治疗患者的方法和调节植物生长的方法。
• Pharmaceutical compositions containing a complex of iron with N-substituted 3-hydroxypyrid-2-one or -4-one derivatives
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0094149A2

  公开（公告）日：1983-11-16

  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 hydrocarbon group and, optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms are also replaced by an aliphatic hydrocarbon group, 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，其中氮原子上的氢原子被脂肪族烃基取代，环碳原子上的一个或多个氢原子也被脂肪族烃基取代，具有治疗缺铁性贫血症的价值。
• Bartulin, J.; Belmar, J.; Gallardo, H., Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 1017 - 1019
  作者：Bartulin, J.、Belmar, J.、Gallardo, H.、Leon, G.

  DOI：——

  日期：——
• Nelson, William O.; Karpishin,Timothy B.; Rettig, Steven J., Canadian Journal of Chemistry, 1988, vol. 66, p. 123 - 131
  作者：Nelson, William O.、Karpishin,Timothy B.、Rettig, Steven J.、Orvig, Cris

  DOI：——

  日期：——