3-(dimethylaminomethyl)aniline-4-pinacol boronate

• 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: 3-(dimethylaminomethyl)aniline-4-pinacol boronate
• 英文别名: 3-[(Dimethylamino)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• 化学式: C₁₅H₂₅BN₂O₂
• 分子量: 276.187
• InChiKey: ACYDXDWTWJLERC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-氟苯基氨基甲酰基)环丙烷羧酸 、 3-(dimethylaminomethyl)aniline-4-pinacol boronate 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium carbonate 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 生成 N-(4-(3-amino-1H-indazol-4-yl)-3-((dimethylamino)methyl)phenyl)-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide
  参考文献：
  名称：

  Discovery and SAR study of c-Met kinase inhibitors bearing an 3-amino-benzo[d]isoxazole or 3-aminoindazole scaffold

  摘要：

  A series of 3-amino-benzo[d]isoxazole-/3-aminoindazole-based compounds were designed, synthesized and pharmacologically evaluated as tyrosine kinase c-Met inhibitors. The SAR study was conducted leading to identification of nine compounds (8d, 8e, 12, 28a-d, 28h and 28i) with IC(50)s less than 10 nM against c-Met. Compound 28a stood out as the most potent c-Met inhibitor displaying potent inhibitory effects both at enzymatic (IC50 = 1.8 nM) and cellular (IC50 = 0.18 mu M on EBC-1 cells) levels. In addition, 28a had a relatively good selectivity compared to a panel of our in-house 14 RTKs. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.002
• 作为产物：
  描述：

  2-(2-(bromomethyl)-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 铁粉 、 氯化铵 、 sodium hydroxide 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 6.0h， 生成 3-(dimethylaminomethyl)aniline-4-pinacol boronate
  参考文献：
  名称：

  A Wulff-type boronate for boronate affinity capture of cis-diol compounds at medium acidic pH condition

  摘要：

  我们设计并合成了一种新的 Wulff 型硼酸盐。将该配体固定在聚合物整体上并酸化为硼酸后，在中酸性 pH 条件下，该配体对顺式二元醇化合物表现出特异的硼酸盐亲和力。

  DOI：

  10.1039/c1cc11096a

文献信息

• Discovery and SAR study of c-Met kinase inhibitors bearing an 3-amino-benzo[d]isoxazole or 3-aminoindazole scaffold
  作者：Xiaolong Jiang、Hongyan Liu、Zilan Song、Xia Peng、Yinchun Ji、Qizheng Yao、Meiyu Geng、Jing Ai、Ao Zhang

  DOI：10.1016/j.bmc.2014.12.002

  日期：2015.2

  A series of 3-amino-benzo[d]isoxazole-/3-aminoindazole-based compounds were designed, synthesized and pharmacologically evaluated as tyrosine kinase c-Met inhibitors. The SAR study was conducted leading to identification of nine compounds (8d, 8e, 12, 28a-d, 28h and 28i) with IC(50)s less than 10 nM against c-Met. Compound 28a stood out as the most potent c-Met inhibitor displaying potent inhibitory effects both at enzymatic (IC50 = 1.8 nM) and cellular (IC50 = 0.18 mu M on EBC-1 cells) levels. In addition, 28a had a relatively good selectivity compared to a panel of our in-house 14 RTKs. (C) 2014 Elsevier Ltd. All rights reserved.
• A Wulff-type boronate for boronate affinity capture of cis-diol compounds at medium acidic pH condition
  作者：Hengye Li、Yunchun Liu、Jing Liu、Zhen Liu

  DOI：10.1039/c1cc11096a

  日期：——

  A new Wulff-type boronate was designed and synthesized. Upon immobilization on a polymeric monolith and acidified as boronic acid, the ligand exhibited specific boronate affinity to cis-diol compounds at medium acidic pH condition.

  我们设计并合成了一种新的 Wulff 型硼酸盐。将该配体固定在聚合物整体上并酸化为硼酸后，在中酸性 pH 条件下，该配体对顺式二元醇化合物表现出特异的硼酸盐亲和力。