6,8-dimethoxy-4-methylquinolin-2(1H)-one | 249737-05-1

• 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-4-methylquinolin-2(1H)-one
• 英文别名: 2(1H)-Quinolinone, 6,8-dimethoxy-4-methyl-；6,8-dimethoxy-4-methyl-1H-quinolin-2-one
• CAS: 249737-05-1
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: TZVDVDRNKWYRNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,8-dimethoxy-4-methylquinolin-2(1H)-one 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.0h， 以65%的产率得到6,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer

  摘要：

  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.

  DOI：

  10.1016/j.steroids.2010.06.004
• 作为产物：
  描述：

  2,4-二甲氧基苯胺 在 硫酸 作用下， 以 水 为溶剂， 反应 0.5h， 生成 6,8-dimethoxy-4-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Long-Wavelength-Absorbing and -Emitting Carbostyrils with High Fluorescence Quantum Yields

  摘要：

  Synthesis, absorption and fluorescence spectra, as well as quantum yields of a series of donor-acceptor-substituted carbostyrils (= quinolin-2(1H)-ones), are reported. Unprecedented strong absorption maxima (epsilon = 10000-20000) close to the visible spectrum, large Stokes shifts up to 130 nm, and quantum yields up to 0.7 are obtained with derivatives containing donor substituents at C(6) and C(7), and either one Ph substituent at C(3) or one CF3 residue at C(4). For analytical applications in biochemistry and medicine, N(1)-functionalization, or amidoacylation at C(3) in the case of the CF3 derivatives, is possible without a concomitant hypsochromic shift of their absorption and emission maxima. Semiempirical molecular-orbital calculations (AM1 for structures, ZINDO for electronic transition energies) prove to bit a suitable tool for the prediction of absorption properties of these compounds. The crystal-structure analysis of 6,7-dimethoxy-1-methyl-3-nitro-4-(trifluoromethyl)quinolin-2-(1H)-one (7) (C13H11F3N2O5, monoclinic, P2(1)/c, a = 12.372(2), b = 12.154(2), c = 10.119(2)Angstrom, beta = 112.95(2)degrees) shows that the NO2 group, squeezed between the CF3 and the C=O group, is oriented almost perpendicularly (87.8(4)degrees) to the ring plane. The intramolecular F ... N distance between the CF3 and the NO2 group is only 2.513(4)Angstrom.

  DOI：

  10.1002/(sici)1522-2675(19990908)82:9<1408::aid-hlca1408>3.0.co;2-q

文献信息

• Synthesis of Casimiroin and Optimization of Its Quinone Reductase 2 and Aromatase Inhibitory Activities
  作者：Arup Maiti、P. V. Narasimha Reddy、Megan Sturdy、Laura Marler、Scott D. Pegan、Andrew D. Mesecar、John M. Pezzuto、Mark Cushman

  DOI：10.1021/jm801335z

  日期：2009.4.9

  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.