1-benzenesulfonyl-5-benzyloxy-2-(5-chloro-pyrazin-3-yl)-1H-indole | 1346163-48-1

• 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: 1-benzenesulfonyl-5-benzyloxy-2-(5-chloro-pyrazin-3-yl)-1H-indole
• 英文别名: 1-(Benzenesulfonyl)-2-(6-chloropyrazin-2-yl)-5-phenylmethoxyindole
• CAS: 1346163-48-1
• 化学式: C₂₅H₁₈ClN₃O₃S
• 分子量: 475.955
• InChiKey: ZVINQXXPRWDAGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  82.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-benzenesulfonyl-5-benzyloxy-2-(5-chloro-pyrazin-3-yl)-1H-indole 在 四(三苯基膦)钯 、 四丁基氟化铵 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 10.5h， 生成 5-benzyloxy-2-[6-(4-methansulfonyl-phenyl)-pyrazin-2-yl]-1H-indole
  参考文献：
  名称：

  Synthesis and biological evaluation of new 3-(6-hydroxyindol-2-yl)-5-(Phenyl) pyridine or pyrazine V-Shaped molecules as kinase inhibitors and cytotoxic agents

  摘要：

  We here report the synthesis and biological evaluation of new 3-[(2-indolyl)]-5-phenyl-3,5-pyridine, 3-[(2-indolyl)]-5-phenyl-2,4-pyridine and 3-[(2-indolyl)]-5-phenyl-2,6-pyrazine derivatives designed as potential CDK inhibitors. Indoles and phenyls were used to generate several substitutions of the pyridine and pyrazine rings. The synthesis included Stille or Suzuki type reactions, which were carried out on the 3,5-dibromopyridine, 2,4-dichloropyridine and 2,6-dichloro-1-4-pyrazine moieties. Cell effects of the V-shaped family were in the micromolar range. Kinase assays were conducted and showed that compound 11 inhibited CDK5 with an inhibitory concentration of 160 nM with a moderate selectivity over GSK3 compared to the reference C which exhibited a slightly lower activity on CDK5 (1.5 mu M). Compound 11 was also found to be the most potent compound in the series and was identified as a new lead for DYRK1A inhibitor discovery (IC50 = 60 nM). Docking studies were carried out in order to investigate the inhibition of DYRK1A. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.048
• 作为产物：
  描述：

  1-phenylsulfonyl-5-benzyloxy-2-tributylstannyl-1H-indole 、 2,6-二氯吡嗪 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以83%的产率得到1-benzenesulfonyl-5-benzyloxy-2-(5-chloro-pyrazin-3-yl)-1H-indole
  参考文献：
  名称：

  Synthesis and biological evaluation of new 3-(6-hydroxyindol-2-yl)-5-(Phenyl) pyridine or pyrazine V-Shaped molecules as kinase inhibitors and cytotoxic agents

  摘要：

  We here report the synthesis and biological evaluation of new 3-[(2-indolyl)]-5-phenyl-3,5-pyridine, 3-[(2-indolyl)]-5-phenyl-2,4-pyridine and 3-[(2-indolyl)]-5-phenyl-2,6-pyrazine derivatives designed as potential CDK inhibitors. Indoles and phenyls were used to generate several substitutions of the pyridine and pyrazine rings. The synthesis included Stille or Suzuki type reactions, which were carried out on the 3,5-dibromopyridine, 2,4-dichloropyridine and 2,6-dichloro-1-4-pyrazine moieties. Cell effects of the V-shaped family were in the micromolar range. Kinase assays were conducted and showed that compound 11 inhibited CDK5 with an inhibitory concentration of 160 nM with a moderate selectivity over GSK3 compared to the reference C which exhibited a slightly lower activity on CDK5 (1.5 mu M). Compound 11 was also found to be the most potent compound in the series and was identified as a new lead for DYRK1A inhibitor discovery (IC50 = 60 nM). Docking studies were carried out in order to investigate the inhibition of DYRK1A. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.048

文献信息

• Synthesis and biological evaluation of new 3-(6-hydroxyindol-2-yl)-5-(Phenyl) pyridine or pyrazine V-Shaped molecules as kinase inhibitors and cytotoxic agents
  作者：Pamela Kassis、Joanna Brzeszcz、Valérie Bénéteau、Olivier Lozach、Laurent Meijer、Rémi Le Guével、Christiane Guillouzo、Krzysztof Lewiński、Stéphane Bourg、Lionel Colliandre、Sylvain Routier、Jean-Yves Mérour

  DOI：10.1016/j.ejmech.2011.08.048

  日期：2011.11

  We here report the synthesis and biological evaluation of new 3-[(2-indolyl)]-5-phenyl-3,5-pyridine, 3-[(2-indolyl)]-5-phenyl-2,4-pyridine and 3-[(2-indolyl)]-5-phenyl-2,6-pyrazine derivatives designed as potential CDK inhibitors. Indoles and phenyls were used to generate several substitutions of the pyridine and pyrazine rings. The synthesis included Stille or Suzuki type reactions, which were carried out on the 3,5-dibromopyridine, 2,4-dichloropyridine and 2,6-dichloro-1-4-pyrazine moieties. Cell effects of the V-shaped family were in the micromolar range. Kinase assays were conducted and showed that compound 11 inhibited CDK5 with an inhibitory concentration of 160 nM with a moderate selectivity over GSK3 compared to the reference C which exhibited a slightly lower activity on CDK5 (1.5 mu M). Compound 11 was also found to be the most potent compound in the series and was identified as a new lead for DYRK1A inhibitor discovery (IC50 = 60 nM). Docking studies were carried out in order to investigate the inhibition of DYRK1A. (C) 2011 Elsevier Masson SAS. All rights reserved.