2-oxo-4-phenethyl-3-(thiazol-2-yl)-1,2-dihydroquinoline-6-carbonitrile | 1259391-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-oxo-4-phenethyl-3-(thiazol-2-yl)-1,2-dihydroquinoline-6-carbonitrile
• CAS: 1259391-59-7
• 化学式: C₂₁H₁₅N₃OS
• 分子量: 357.436
• InChiKey: CYWSUTOANNVORI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  69.54
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-oxo-4-phenethyl-3-(thiazol-2-yl)-1,2-dihydroquinoline-6-carbonitrile 在 氨 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 6-(aminomethyl)-4-phenethyl-3-(thiazol-2-yl)quinolin-2(1H)-one
  参考文献：
  名称：

  Discovery of novel quinolinone adenosine A2B antagonists

  摘要：

  A novel series of quinolinone-based adenosine A(2B) receptor antagonists was identified via high throughput screening of an encoded combinatorial compound collection. Synthesis and assay of a series of analogs highlighted essential structural features of the initial hit. Optimization resulted in an A2B antagonist (2i) which exhibited potent activity in a cAMP accumulation assay (5.1 nM) and an IL-8 release assay (0.4 nM). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.030
• 作为产物：
  描述：

  zinc(II) cyanide 、 6-chloro-4-phenethyl-3-(thiazol-2-yl)quinolin-2(1H)-one 在 racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl 、 palladium(II) trifluoroacetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 1.0h， 生成 2-oxo-4-phenethyl-3-(thiazol-2-yl)-1,2-dihydroquinoline-6-carbonitrile
  参考文献：
  名称：

  Discovery of novel quinolinone adenosine A2B antagonists

  摘要：

  A novel series of quinolinone-based adenosine A(2B) receptor antagonists was identified via high throughput screening of an encoded combinatorial compound collection. Synthesis and assay of a series of analogs highlighted essential structural features of the initial hit. Optimization resulted in an A2B antagonist (2i) which exhibited potent activity in a cAMP accumulation assay (5.1 nM) and an IL-8 release assay (0.4 nM). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.030