N-(3,4-dihydroxy-benzyl)-nicotinamide | 57894-16-3

• 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: N-(3,4-dihydroxy-benzyl)-nicotinamide
• 英文别名: 1-Methylnicotinamido-catechol；N-[(3,4-dihydroxyphenyl)methyl]pyridine-3-carboxamide
• CAS: 57894-16-3
• 化学式: C₁₃H₁₂N₂O₃
• 分子量: 244.25
• InChiKey: HLTYTJUGJBZSAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  82.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3,4-dihydroxy-benzyl)-nicotinamide 、 丁二酸 、 三氯氧磷 以50%的产率得到
  参考文献：
  名称：

  TIWARI S. S.; PANDEY V. K., J. INDIAN CHEM. SOC. , 1975, 52, NO 8, 777-779

  摘要：

  DOI：
• 作为产物：
  描述：

  3-吡啶乙酸 、 3,4-二羟基苄胺·氢溴酸 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(3,4-dihydroxy-benzyl)-nicotinamide
  参考文献：
  名称：

  Catechols and 3-hydroxypyridones as inhibitors of the DNA repair complex ERCC1-XPF

  摘要：

  Catechol-based inhibitors of ERCC1-XPF endonuclease activity were identified from a high-throughput screen. Exploration of the structure-activity relationships within this series yielded compound 13, which displayed an ERCC1-XPF IC50 of 0.6 mu M, high selectivity against FEN-1 and DNase I and activity in nucleotide excision repair, cisplatin enhancement and gamma H2AX assays in A375 melanoma cells. Screening of fragments as potential alternatives to the catechol group revealed that 3-hydroxypyridones are able to inhibit ERCC1-XPF with high ligand efficiency, and elaboration of the hit gave compounds 36 and 37 which showed promising ERCC1-XPF IC50 values of <10 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.031

文献信息

• Catechols and 3-hydroxypyridones as inhibitors of the DNA repair complex ERCC1-XPF
  作者：Timothy M. Chapman、Kevin J. Gillen、Claire Wallace、Maximillian T. Lee、Preeti Bakrania、Puneet Khurana、Peter J. Coombs、Laura Stennett、Simon Fox、Emilie A. Bureau、Janet Brownlees、David W. Melton、Barbara Saxty

  DOI：10.1016/j.bmcl.2015.08.031

  日期：2015.10

  Catechol-based inhibitors of ERCC1-XPF endonuclease activity were identified from a high-throughput screen. Exploration of the structure-activity relationships within this series yielded compound 13, which displayed an ERCC1-XPF IC50 of 0.6 mu M, high selectivity against FEN-1 and DNase I and activity in nucleotide excision repair, cisplatin enhancement and gamma H2AX assays in A375 melanoma cells. Screening of fragments as potential alternatives to the catechol group revealed that 3-hydroxypyridones are able to inhibit ERCC1-XPF with high ligand efficiency, and elaboration of the hit gave compounds 36 and 37 which showed promising ERCC1-XPF IC50 values of <10 mu M. (C) 2015 Elsevier Ltd. All rights reserved.
• TIWARI S. S.; PANDEY V. K., J. INDIAN CHEM. SOC. <JICS-AH>, 1975, 52, NO 8, 777-779
  作者：TIWARI S. S.、 PANDEY V. K.

  DOI：——

  日期：——