1,6-dimethyl-3-benzyloxy-pyridin-4(1H)-one-2-carboxyamide | 347393-44-6

• 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: 1,6-dimethyl-3-benzyloxy-pyridin-4(1H)-one-2-carboxyamide
• 英文别名: 1,6-Dimethyl-4-oxo-3-phenylmethoxypyridine-2-carboxamide；1,6-dimethyl-4-oxo-3-phenylmethoxypyridine-2-carboxamide
• CAS: 347393-44-6
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: LIPQNUFRLBJNLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6-dimethyl-3-benzyloxy-pyridin-4(1H)-one-2-carboxyamide 在 palladium on activated charcoal 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以92%的产率得到1,6-dimethyl-3-hydroxypyridin-4(1H)-one-2-carboxy-amide
  参考文献：
  名称：

  Synthesis of 2-amido-3-hydroxypyridin-4(1H)-ones: novel iron chelators with enhanced pFe3+ values

  摘要：

  The synthesis of a range of 2-amido-3-hydroxypyridin-4-ones as bidentate iron(III) chelators with potential for oral administration is described. The pKa values of the ligands together with the stability constants of their iron(III) complexes have been determined. Results indicate that the introduction of an amido substituent at the 2-position leads to an appreciable enhancement of the pFe(3+) values. The ability of these novel 3-hydroxypyridin-4-ones to facilitate the iron excretion in bile was investigated using a Fe-59-ferritin loaded rat model. The optimal effect was observed with the N-methyl amido derivative 15b, which has an associated pFe(3+) value of 21.7, more than two orders of magnitude higher than that of deferiprone (1,2-dimethyl-3-hydroxypyridin-4-one) 1a (pFe(3+) = 19.4). Dose response studies suggest that chelators with high pFe(3+) values scavenge iron more effectively at lower doses when compared with simple dialkyl substituted hydroxypyridinones. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00273-x
• 作为产物：
  描述：

  2-甲酰基-3-苄氧基-6-甲基-吡喃-4(1H)-酮 在 4-二甲氨基吡啶 、 sodium chlorite 、 氨基磺酸 、 氨 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 37.0h， 生成 1,6-dimethyl-3-benzyloxy-pyridin-4(1H)-one-2-carboxyamide
  参考文献：
  名称：

  Synthesis of 2-amido-3-hydroxypyridin-4(1H)-ones: novel iron chelators with enhanced pFe3+ values

  摘要：

  The synthesis of a range of 2-amido-3-hydroxypyridin-4-ones as bidentate iron(III) chelators with potential for oral administration is described. The pKa values of the ligands together with the stability constants of their iron(III) complexes have been determined. Results indicate that the introduction of an amido substituent at the 2-position leads to an appreciable enhancement of the pFe(3+) values. The ability of these novel 3-hydroxypyridin-4-ones to facilitate the iron excretion in bile was investigated using a Fe-59-ferritin loaded rat model. The optimal effect was observed with the N-methyl amido derivative 15b, which has an associated pFe(3+) value of 21.7, more than two orders of magnitude higher than that of deferiprone (1,2-dimethyl-3-hydroxypyridin-4-one) 1a (pFe(3+) = 19.4). Dose response studies suggest that chelators with high pFe(3+) values scavenge iron more effectively at lower doses when compared with simple dialkyl substituted hydroxypyridinones. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00273-x

文献信息

• PROCESSES FOR THE MANUFACTURING OF 3-HYDROXY-N,1,6-TRIALKYL-4-OXO-1,4-DIHYDROPYRIDINE-2-CARBOXAMIDE
  申请人：APOTEX INC.

  公开号：EP1440061B1

  公开（公告）日：2007-04-11
• Synthesis of 2-amido-3-hydroxypyridin-4(1H)-ones: novel iron chelators with enhanced pFe3+ values
  作者：Zu D. Liu、S. Piyamongkol、Ding Y. Liu、Hicham H. Khodr、Shu L. Lu、Robert C. Hider

  DOI：10.1016/s0968-0896(00)00273-x

  日期：2001.3

  The synthesis of a range of 2-amido-3-hydroxypyridin-4-ones as bidentate iron(III) chelators with potential for oral administration is described. The pKa values of the ligands together with the stability constants of their iron(III) complexes have been determined. Results indicate that the introduction of an amido substituent at the 2-position leads to an appreciable enhancement of the pFe(3+) values. The ability of these novel 3-hydroxypyridin-4-ones to facilitate the iron excretion in bile was investigated using a Fe-59-ferritin loaded rat model. The optimal effect was observed with the N-methyl amido derivative 15b, which has an associated pFe(3+) value of 21.7, more than two orders of magnitude higher than that of deferiprone (1,2-dimethyl-3-hydroxypyridin-4-one) 1a (pFe(3+) = 19.4). Dose response studies suggest that chelators with high pFe(3+) values scavenge iron more effectively at lower doses when compared with simple dialkyl substituted hydroxypyridinones. (C) 2001 Elsevier Science Ltd. All rights reserved.