2-Ethyl-3-hydroxy-1-(2-piperidin-1-ylethyl)pyridin-4-one | 761386-17-8

• 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: 2-Ethyl-3-hydroxy-1-(2-piperidin-1-ylethyl)pyridin-4-one
• CAS: 761386-17-8
• 化学式: C₁₄H₂₂N₂O₂
• 分子量: 250.341
• InChiKey: KPVRELTVHZUNCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙基-3-苯基甲氧基吡喃-4-酮 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 生成 2-Ethyl-3-hydroxy-1-(2-piperidin-1-ylethyl)pyridin-4-one
  参考文献：
  名称：

  Design, Synthesis and Evaluation of N-Basic Substituted 3-Hydroxypyridin-4-ones: Orally Active Iron Chelators with Lysosomotrophic Potential

  摘要：

  研究调查将螯合剂定位到溶酶体铁库的可能性，合成了具有碱性链的九种双齿3-羟基吡啶-4-酮。由于铁蛋白铁的周转集中在溶酶体中，这种策略预计将提高双齿配体的螯合剂效力。 这些配体的pKa值以及它们在1-辛醇和4-吗啉丙磺酸盐缓冲液（MOPS）pH 7.4之间的分配系数已经确定。在一个59Fe-铁蛋白负载的大鼠模型中，已经研究了这些碱性3-羟基吡啶-4-酮的体内铁动员效力。尽管观察到与侧链pKa值之间没有明显的相关性，但具有pKa值大于7.0的倾向于比具有pKa值小于7.0的更有效。含有咪唑基的分子比三级胺衍生物要不太有效。剂量-反应研究表明，与N-烷基羟基吡啶酮相比，基本吡啶酮在较低剂量时相对更有效。 在哌啶衍生物4h和4i中观察到最佳效果。在150 μmol kg−1剂量下，衍生物4i比广泛采用的450 μmol kg−1去铁胺更有效。

  DOI：

  10.1211/0022357001773940

文献信息

• FLUORINATED DERIVATES OF 3-HYDROXYPYRIDIN-4-ONES
  申请人：Tam Tim Fat

  公开号：US20120270882A1

  公开（公告）日：2012-10-25

  Provided are compounds of Formula I which are derivatives of 3-Hydroxypyridin-4-ones. The compounds may be used in treatment of a medical condition related to a toxic concentration of iron. The compounds may be used for preparation of a medicament for treatment of a medical condition related to a toxic concentration of iron. The medical condition related to a toxic concentration of iron may be selected from the group consisting of: cancer, pulmonary disease, progressive kidney disease and Frederich's Ataxia.

  提供的是公式I的化合物，它们是3-羟基吡啶-4-酮的衍生物。这些化合物可以用于治疗与铁的毒性浓度相关的医疗状况。这些化合物可以用于制备治疗与铁的毒性浓度相关的医疗状况的药物。与铁的毒性浓度相关的医疗状况可以从以下组中选择：癌症、肺部疾病、进行性肾脏疾病和弗里德里希共济失调症。
• FLUORINATED DERIVATIVES OF 3-HYDROXYPYRIDIN-4-ONES
  申请人：APOTEX TECHNOLOGIES INC.

  公开号：US20150335626A1

  公开（公告）日：2015-11-26

  Provided are compounds of Formula I which are derivatives of 3-Hydroxypyridin-4-ones. The compounds may be used in treatment of a medical condition related to a toxic concentration of iron. The compounds may be used for preparation of a medicament for treatment of a medical condition related to a toxic concentration of iron. The medical condition related to a toxic concentration of iron may be selected from the group consisting of: cancer, pulmonary disease, progressive kidney disease and Frederich's Ataxia.

  提供的是I式化合物，它们是3-羟基吡啶-4-酮的衍生物。这些化合物可用于治疗与铁的毒性浓度相关的医疗状况。这些化合物可用于制备治疗与铁的毒性浓度相关的医疗状况的药物。与铁的毒性浓度相关的医疗状况可从以下组中选择：癌症，肺部疾病，进行性肾脏疾病和弗里德里希共济失调症。
• Fluorinated Derivatives of 3-Hydroxypyridin-4-Ones
  申请人：Apotex Technologies Inc.

  公开号：US20160083346A1

  公开（公告）日：2016-03-24

  Compounds of Formula I which are derivatives of 3-Hydroxypyridin-4-ones. The compounds may be used in treatment of a medical condition related to a toxic concentration of iron. The compounds may be used for preparation of a medicament for treatment of a medical condition related to a toxic concentration of iron. The medical condition related to a toxic concentration of iron may be selected from the group consisting of: cancer, pulmonary disease, progressive kidney disease and Friedreich's ataxia.

  公式I的衍生物化合物是3-羟基吡啶-4-酮的衍生物。这些化合物可用于治疗与铁的毒性浓度相关的医疗状况。这些化合物可用于制备治疗与铁的毒性浓度相关的医疗状况的药物。与铁毒性浓度相关的医疗状况可以从以下组中选择：癌症、肺病、进行性肾病和弗里德赫氏共济失调。
• Basic 3-hydroxypyridin-4-ones: Potential antimalarial agents
  作者：Lotfollah S. Dehkordi、Zu D. Liu、Robert C. Hider

  DOI：10.1016/j.ejmech.2007.07.011

  日期：2008.5

  3-Hydroxypyridin-4-ones selectively bind iron under biological conditions and one such compound has found application in the treatment of thalassaemia-linked iron overload. Related molecules have also been demonstrated to possess an antimalarial effect at levels which are non-toxic to mammalian cells. In an attempt to improve the efficiency of such molecules we have investigated the effect of introducing basic nitrogen centres into 3-hydroxypyridin-4-ones in an attempt to achieve targeting to lysosomes and other intracellular acidic vacuoles. Several of the compounds reported in this communication possess enhanced antimalarial activity over that of the simple hydroxypyridinone class. (C) 2007 Elsevier Masson SAS. All rights reserved.
• "Fluorinated Derivatives of 3-Hydroxypyridin-4-Ones"
  申请人：Apotex Technologies Inc.

  公开号：US20170247329A1

  公开（公告）日：2017-08-31

  Compounds of Formula I which are derivatives of 3-Hydroxypyridin-4-ones. The compounds may be used in treatment of a medical condition related to a toxic concentration of iron. The compounds may be used for preparation of a medicament for treatment of a medical condition related to a toxic concentration of iron. The medical condition related to a toxic concentration of iron may be selected from the group consisting of: cancer, pulmonary disease, progressive kidney disease and Friedreich's ataxia.