6,8-Dimethoxy-4-chinolinol | 92288-60-3

• 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-chinolinol
• 英文别名: 6,8-dimethoxyquinolin-4-ol；6,8-dimethoxy-1H-quinolin-4-one
• CAS: 92288-60-3
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: VWADZMOPSMTDGX-UHFFFAOYSA-N

物化性质

• 沸点：
  393.8±37.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,8-Dimethoxy-4-chinolinol 在 三溴化磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以40%的产率得到4-bromo-6,8-dimethoxyquinoline
  参考文献：
  名称：

  Assembly of 4-Aminoquinolines via Palladium Catalysis:  A Mild and Convenient Alternative to S_NAr Methodology

  摘要：

  4-Aminoquinolines, classically prepared via SNAr chemistry from an amine and 4-haloquinoline, are important scaffolds in medicinal chemistry. Interest in these compounds prompted us to explore palladium catalysis as an alternative to the existing methods for their preparation. Initial results followed by an iterative screening paradigm confirmed Pd(OAc)(2)/ DPEphos/K3PO4 as a mild and convenient alternative for the formation of the C-N bond in 4-aminoquinolines. A description of the screen and the scope of this methodology are discussed herein.

  DOI：

  10.1021/jo062168u
• 作为产物：
  描述：

  2,4-二甲氧基苯胺 在 二苯甲酮 作用下， 反应 1.0h， 生成 6,8-Dimethoxy-4-chinolinol
  参考文献：
  名称：

  Hypoxia-Selective Antitumor Agents. 15. Modification of Rate of Nitroreduction and Extent of Lysosomal Uptake by Polysubstitution of 4-(Alkylamino)-5-nitroquinoline Bioreductive Drugs

  摘要：

  Studies have shown that 4-(alkylamino)-5-nitroquinolines possess high selectivity (20-60-fold) for hypoxic tumor cells in vitro, but are not active as hypoxia-selective cytotoxins (HSCs) in vivo. The compounds show inadequate rates of extravascular diffusion, likely due both to sequestration of the bisbasic compounds into lysosomes and rapid nitroreduction. A further series of analogues, designed to counteract these limitations, has been synthesized and evaluated. Analogues bearing one to three electron-donating substituents on the quinoline have one-electron reduction potentials up to 100 mV lower than that of the unsubstituted compound (5), but do not have improved biological activity. The relationship between hypoxic selectivity and rates of metabolic reduction suggests at least two mechanisms of cytotoxicity for this series of 5-nitroquinolines. Compounds with high rates of reduction are toxic via oxygen-sensitive net bioreduction, while compounds which are poor substrates for nitroreduction are toxic through an oxygen-insensitive non-bioreductive mechanism. As rates of metabolic reduction are lowered, the non-bioreductive mechanism of toxicity becomes dominant and hypoxic selectivity is lost. A small series of analogues bearing hydrophilic but neutral side chains were also prepared. Compounds with a dihydroxypropyl side chain retained cytotoxic potency and hypoxic cell selectivity in cell culture assays, and had lowered uptake into lysosomes, but none of three analogues evaluated against KHT tumors in mice showed activity as an HSC in vivo.

  DOI：

  10.1021/jm9607865

文献信息

• A visible-light-irradiated electron donor-acceptor complex-promoted radical reaction system for the C H perfluoroalkylation of quinolin-4-ols
  作者：Yunze Li、Min Rao、Zhenwei Fan、Baoyi Nian、Yaofeng Yuan、Jiajia Cheng

  DOI：10.1016/j.tetlet.2019.151046

  日期：2019.9

  An efficient method for visible-light-induced perfluoroalkylaion of quinolin-4-ol has been reported. In the presence of t-BuONa and perfluoroalkyl iodide, quinolin-4-ol underwent CH perfluoroalkylation under the irradiation of green light. Mechanistic studies demonstrated that visible-light promoted intermolecular charge transfer within the transient electron donor-acceptor complex in the absence of

  已经报道了可见光诱导的喹啉-4-醇全氟烷基阴离子的有效方法。在t- BuONa和全氟烷基碘的存在下，喹啉-4-醇在绿光照射下经历了C H全氟烷基化。机理研究表明，在没有任何光催化剂的情况下，可见光促进了瞬态电子供体-受体复合物中分子间的电荷转移。
• Quinoline derivatives as immunostimulants
  申请人：Pfizer Inc.

  公开号：US05506235A1

  公开（公告）日：1996-04-09

  This invention relates to compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are as defined hereinbelow that exhibit activity as immunostimulants.

  这项发明涉及公式##STR1##中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5、R.sup.6和R.sup.7的化合物，这些化合物作为免疫刺激剂表现出活性。
• N-ω-Carbethoxypentyl-4-quinolones: A New Class of Leukotriene Biosynthesis Inhibitors
  作者：Nicoletta Desideri、Isabella Sestili、Maria Luisa Stein、Stefano Manarini、Giuseppe Dell'Elba、Chiara Cerletti

  DOI：10.1002/ardp.19973300404

  日期：——

  6‐[(4‐Quinolinyl)oxy]hexanoic acids and the corresponding esters were designed and synthesized as inhibitors of the production of arachidonic acid metabolites. The inhibitory activities were assayed in vitro by evaluation of serum leukotriene B4 and thromboxane B2 production. While all 6‐[(4‐quinolinyl)oxy]hexanoic acids and their esters proved to be inactive, the N‐alkyl‐4‐quinolones, obtained as

  6 - [(4 - Quinolinyl) oxy] 己酸和相应的酯被设计和合成作为花生四烯酸代谢物产生的抑制剂。通过评估血清白三烯 B4 和血栓素 B2 的产生在体外测定了抑制活性。虽然所有 6 - [(4- quinolinyl) oxy] 己酸及其酯被证明是无活性的，但在其合成过程中作为副产物获得的 N-烷基 - 4- 喹诺酮被发现是一类新的白三烯生物合成抑制剂。
• 4(1H)-quinolone derivatives
  申请人：KIRIN BEER KABUSHIKI KAISHA

  公开号：EP0343574B1

  公开（公告）日：1994-07-27
• QUINOLINE DERIVATIVES AS IMMUNOSTIMULANTS
  申请人：PFIZER INC.

  公开号：EP0597003A1

  公开（公告）日：1994-05-18