4-Hydroxy-1-methyl-7.8-methylendioxy-2-oxo-chinolin | 477-34-9

• 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: 4-Hydroxy-1-methyl-7.8-methylendioxy-2-oxo-chinolin
• 英文别名: 6-hydroxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one；6-hydroxy-9-methyl-9H-[1,3]dioxolo[4,5-h]quinolin-8-one；6-Hydroxy-9-methyl-9H-[1,3]dioxolo[4,5-h]chinolin-8-on；6-Hydroxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8-one；6-hydroxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8-one
• CAS: 477-34-9
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: WUELIFZILLNRBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-1-methyl-7.8-methylendioxy-2-oxo-chinolin 、 [11C]methyl triflate 在 sodium hydride 作用下， 以 乙腈 为溶剂， 生成 6-[(11)C]methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-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：

  4-isocyanato-benzo[1,3]dioxole 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 生成 4-Hydroxy-1-methyl-7.8-methylendioxy-2-oxo-chinolin
  参考文献：
  名称：

  杂环化合物-V：辣椒素的合成

  摘要：

  将乙氧基乙炔加到异氰酸2，3-亚甲基二氧基苯基酯中，得到4-乙氧基-7，8-亚甲基二氧基-2-喹诺酮。喹诺酮的N-甲基化，然后乙氧基水解，并用重氮甲烷处理，得到4-甲氧基-1-甲基-7,8-亚甲基二氧基-2-喹诺酮。该反应序列提供了天然存在的化合物卡西罗林的合成。

  DOI：

  10.1016/s0040-4020(01)99173-2

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.
• Kincl et al., Journal of the Chemical Society, 1956, p. 4163,4168
  作者：Kincl et al.

  DOI：——

  日期：——