3-isobutyl-6-nitroquinazolin-4(3H)-one | 900513-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-isobutyl-6-nitroquinazolin-4(3H)-one
• 英文别名: 3-(2-methylpropyl)-6-nitroquinazolin-4-one
• CAS: 900513-10-2
• 化学式: C₁₂H₁₃N₃O₃
• mdl: MFCD07331887
• 分子量: 247.254
• InChiKey: JJVRPHSDWHIZQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-isobutyl-6-nitroquinazolin-4(3H)-one 在 palladium on activated charcoal 吡啶 、 copper(l) iodide 、 溴 、 甲酸铵 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 8-Isobutyl-9-oxo-8,9-dihydro-thiazolo[5,4-f]quinazoline-2-carbonitrile
  参考文献：
  名称：

  Thiazolo[5,4-f]quinazolin-9-ones, inhibitors of glycogen synthase kinase-3

  摘要：

  In an effort to identify new protein kinase inhibitors with increased potency and selectivity, we have developed the microwave-assisted synthesis of thiazolo[5,4-f]quinazolin-9-ones. The effects of eighteen derivatives on CDK1/cyclin B, CDK5/p25, and GSK-3 were investigated. Several turned out to inhibit GSK-3 in the micromolar range. Molecular modeling studies suggest that the most selective GSK-3 inhibitors 7a-d bind into the ATP-binding site through a key hydrogen bond interaction with Val135 and target the specific hydrophobic backpocket of the enzyme. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.006
• 作为产物：
  描述：

  碘代异丁烷 、 6-硝基喹唑啉-4(3H)-酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3-isobutyl-6-nitroquinazolin-4(3H)-one
  参考文献：
  名称：

  Thiazolo[5,4-f]quinazolin-9-ones, inhibitors of glycogen synthase kinase-3

  摘要：

  In an effort to identify new protein kinase inhibitors with increased potency and selectivity, we have developed the microwave-assisted synthesis of thiazolo[5,4-f]quinazolin-9-ones. The effects of eighteen derivatives on CDK1/cyclin B, CDK5/p25, and GSK-3 were investigated. Several turned out to inhibit GSK-3 in the micromolar range. Molecular modeling studies suggest that the most selective GSK-3 inhibitors 7a-d bind into the ATP-binding site through a key hydrogen bond interaction with Val135 and target the specific hydrophobic backpocket of the enzyme. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.006