6,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one | 1137557-82-4

• 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: 6,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
• 英文别名: 6,8-dimethoxy-1,4-dimethylquinolin-2-one
• CAS: 1137557-82-4
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: BYYQQWLTZFBHIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2,4-dimethoxyphenyl)-N-methyl-3-oxobutanamide 在 PPA 作用下， 以17%的产率得到6,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis of Casimiroin and Optimization of Its Quinone Reductase 2 and Aromatase Inhibitory Activities

  摘要：

  An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.

  DOI：

  10.1021/jm801335z

文献信息

• Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer
  作者：Min Wang、Mingzhang Gao、Kathy D. Miller、George W. Sledge、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.steroids.2010.06.004

  日期：2010.12

  Carbon-11-labeled casimiroin analogues were first designed and synthesized as new potential PET agents for imaging of quinone reductase (QR) 2 and aromatase expression in breast cancer. [C-11]casimiroin (6-[C-11]rnethoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one, [C-11]11) and its carbon-11-labeled analogues 5,6,8-trimethoxy-1-[C-11]methyl-4-methylquinolin-2(1H)-one ([C-11]17), 8-methoxy-1-[C-11]methyl-4-methylquinolin-2(1H)-one ((11)[C]21a), 6,8-dimethoxy-1-(11)[C]methyl-4-methylquinolin-2(1H)-one ([C-11]21b), and 5,8-dimethoxy-1-[C-11]methyl-4-methylquinolin-2(1H)-one ([C-11]21c), were prepared from their corresponding precursors with [C-11]methyl triflate ([C-11]CH3OTf) under basic conditions (NaH) through either O- or N-[C-11]methylation and isolated by semi-preparative HPLC method in 40-50% radiochemical yields decay corrected to end of bombardment (EOB), based on [C-11]CO2, and 111-185 GBq/mu mol specific activity at the end of synthesis (EOS). (C) 2010 Elsevier Inc. All rights reserved.