5-Bromo-7-(piperidin-4-ylmethylcarbamoyl)benzofuran-2-carboxylic acid | 1310356-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-Bromo-7-(piperidin-4-ylmethylcarbamoyl)benzofuran-2-carboxylic acid
• 英文别名: 5-bromo-7-(piperidin-4-ylmethylcarbamoyl)-1-benzofuran-2-carboxylic acid
• CAS: 1310356-14-9
• 化学式: C₁₆H₁₇BrN₂O₄
• 分子量: 381.226
• InChiKey: JQSPCDBDHCGFCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 5-bromo-3-formyl-2-hydroxybenzoate 在 水 、 potassium carbonate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 生成 5-Bromo-7-(piperidin-4-ylmethylcarbamoyl)benzofuran-2-carboxylic acid
  参考文献：
  名称：

  The discovery of novel benzofuran-2-carboxylic acids as potent Pim-1 inhibitors

  摘要：

  Novel benzofuran-2-carboxylic acids, exemplified by 29, 38 and 39, have been discovered as potent Pim-1 inhibitors using fragment based screening followed by X-ray structure guided medicinal chemistry optimization. The compounds demonstrate potent inhibition against Pim-1 and Pim-2 in enzyme assays. Compound 29 has been tested in the Ambit 442 kinase panel and demonstrates good selectivity for the Pim kinase family. X-ray structures of the inhibitor/Pim-1 binding complex reveal important salt-bridge and hydrogen bond interactions mediated by the compound's carboxylic acid and amino groups. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.030

文献信息

• The discovery of novel benzofuran-2-carboxylic acids as potent Pim-1 inhibitors
  作者：Yibin Xiang、Bradford Hirth、Gary Asmussen、Hans-Peter Biemann、Kimberly A. Bishop、Andrew Good、Maria Fitzgerald、Tatiana Gladysheva、Annuradha Jain、Katherine Jancsics、Jinyu Liu、Markus Metz、Andrew Papoulis、Renato Skerlj、J. David Stepp、Ronnie R. Wei

  DOI：10.1016/j.bmcl.2011.03.030

  日期：2011.5

  Novel benzofuran-2-carboxylic acids, exemplified by 29, 38 and 39, have been discovered as potent Pim-1 inhibitors using fragment based screening followed by X-ray structure guided medicinal chemistry optimization. The compounds demonstrate potent inhibition against Pim-1 and Pim-2 in enzyme assays. Compound 29 has been tested in the Ambit 442 kinase panel and demonstrates good selectivity for the Pim kinase family. X-ray structures of the inhibitor/Pim-1 binding complex reveal important salt-bridge and hydrogen bond interactions mediated by the compound's carboxylic acid and amino groups. (C) 2011 Elsevier Ltd. All rights reserved.