3-(4-phenoxyphenyl)-7-(1-(prop-2-yn-1-yl)-1H-pyrazol-4-yl)thieno[3,2-c]pyridin-4-amine

• 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-(4-phenoxyphenyl)-7-(1-(prop-2-yn-1-yl)-1H-pyrazol-4-yl)thieno[3,2-c]pyridin-4-amine
• 英文别名: 3-(4-phenoxyphenyl)-7-(1-(prop-2-yn-1-yl)-1H-pyrazol-4-yl)thiophene[3,2-c]pyridine-4 -amine；3-(4-Phenoxyphenyl)-7-(1-prop-2-ynylpyrazol-4-yl)thieno[3,2-c]pyridin-4-amine；3-(4-phenoxyphenyl)-7-(1-prop-2-ynylpyrazol-4-yl)thieno[3,2-c]pyridin-4-amine
• 化学式: C₂₅H₁₈N₄OS
• 分子量: 422.51
• InChiKey: AIJJEYUTVNTQLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-溴噻吩并[3,2-c]吡啶-4-胺 在 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium carbonate 、 potassium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 生成 3-(4-phenoxyphenyl)-7-(1-(prop-2-yn-1-yl)-1H-pyrazol-4-yl)thieno[3,2-c]pyridin-4-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 7-substituted 3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amines as potent Bruton’s tyrosine kinase (BTK) inhibitors

  摘要：

  A series of novel 7-substituted 3-(4-phenoxyphenyl)thieno[3,2-c] pyridin-4-amines as potent BTK inhibitors were designed, synthesized and evaluated. These thieno[3,2-c] pyridin-4-amine derivatives displayed variant inhibitory activities against BTK in vitro. Among these, 7-pyrazol-4-yl substituted 3-(4-phenoxyphenyl) thieno[3,2-c] pyridin-4-amine subseries showed high BTK inhibition and several compounds displayed superior BTK inhibitory activity. Comprehensive SAR was disclosed and compound 13b showed excellent potency (IC50 = 11.8 nM), outstanding hydrophilicity (AlogP = 3.53), and relatively good kinase selectivity, being a promising lead for further evaluation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.039

文献信息

• Synthesis and biological evaluation of novel 7-substituted 3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amines as potent Bruton’s tyrosine kinase (BTK) inhibitors
  作者：Minhang Xin、Xinge Zhao、Wei Huang、Qiu Jin、Gang Wu、Yazhou Wang、Feng Tang、Hua Xiang

  DOI：10.1016/j.bmc.2015.08.039

  日期：2015.10

  A series of novel 7-substituted 3-(4-phenoxyphenyl)thieno[3,2-c] pyridin-4-amines as potent BTK inhibitors were designed, synthesized and evaluated. These thieno[3,2-c] pyridin-4-amine derivatives displayed variant inhibitory activities against BTK in vitro. Among these, 7-pyrazol-4-yl substituted 3-(4-phenoxyphenyl) thieno[3,2-c] pyridin-4-amine subseries showed high BTK inhibition and several compounds displayed superior BTK inhibitory activity. Comprehensive SAR was disclosed and compound 13b showed excellent potency (IC50 = 11.8 nM), outstanding hydrophilicity (AlogP = 3.53), and relatively good kinase selectivity, being a promising lead for further evaluation. (C) 2015 Elsevier Ltd. All rights reserved.