AG 5

• 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: AG 5
• 英文别名: N-[2-(benzylamino)-2-oxoethyl]-3-hydroxy-4-oxo-1H-pyridine-2-carboxamide;hydrochloride
• 化学式: C₁₅H₁₅N₃O₄*ClH
• 分子量: 337.763
• InChiKey: DUYAKYYVTIYWAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  108
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  麦芽醇 在 sodium chlorite 、 氨基磺酸 、 氨 、 三氧化硫吡啶 、 三氯化硼 、 1-羟基苯并三唑 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 sodium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 27.0h， 生成 AG 5
  参考文献：
  名称：

  Synthesis, physical–chemical characterisation and biological evaluation of novel 2-amido-3-hydroxypyridin-4(1H)-ones: Iron chelators with the potential for treating Alzheimer’s disease

  摘要：

  A novel class of 2-amido-3-hydroxypyridin-4-one iron chelators is described. These compounds have been designed to behave as suitable molecular probes which will improve our knowledge of the role of iron in neurodegenerative conditions. Neurodegenerative disorders, such as Alzheimer's disease (AD) and Parkinson disease (PD), can be considered as diverse pathological conditions sharing critical metabolic processes such as protein aggregation and oxidative stress. Interestingly, both these metabolic alterations seem to be associated with the involvement of metal ions, including iron. Iron chelation is therefore a potential therapeutic approach. The physico-chemical (pK(a) pFe(3+) and log P) and biological properties (inhibition of iron-containing enzymes) of these chelators have been investigated in order to obtain a suitable profile for the treatment of neurodegenerative conditions. Studies with neuronal cell cultures confirm that the new iron chelators are neuroprotective against beta-amyloid-induced toxicity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.007

文献信息

• Synthesis, physical–chemical characterisation and biological evaluation of novel 2-amido-3-hydroxypyridin-4(1H)-ones: Iron chelators with the potential for treating Alzheimer’s disease
  作者：Alessandra Gaeta、Francisco Molina-Holgado、Xiao L. Kong、Sarah Salvage、Sarah Fakih、Paul T. Francis、Robert J. Williams、Robert C. Hider

  DOI：10.1016/j.bmc.2010.12.007

  日期：2011.2

  A novel class of 2-amido-3-hydroxypyridin-4-one iron chelators is described. These compounds have been designed to behave as suitable molecular probes which will improve our knowledge of the role of iron in neurodegenerative conditions. Neurodegenerative disorders, such as Alzheimer's disease (AD) and Parkinson disease (PD), can be considered as diverse pathological conditions sharing critical metabolic processes such as protein aggregation and oxidative stress. Interestingly, both these metabolic alterations seem to be associated with the involvement of metal ions, including iron. Iron chelation is therefore a potential therapeutic approach. The physico-chemical (pK(a) pFe(3+) and log P) and biological properties (inhibition of iron-containing enzymes) of these chelators have been investigated in order to obtain a suitable profile for the treatment of neurodegenerative conditions. Studies with neuronal cell cultures confirm that the new iron chelators are neuroprotective against beta-amyloid-induced toxicity. (C) 2010 Elsevier Ltd. All rights reserved.