2-phenylpyrimido[4,5-b]quinolin-4(3H)-one

• 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: 2-phenylpyrimido[4,5-b]quinolin-4(3H)-one
• 英文别名: 2-Phenylpyrimido[4,5-b]quinolin-4-ol；2-phenyl-3H-pyrimido[4,5-b]quinolin-4-one
• 化学式: C₁₇H₁₁N₃O
• 分子量: 273.294
• InChiKey: MZKLSOUYNBYHCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 2-phenylpyrimido[4,5-b]quinolin-4(3H)-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以80%的产率得到10-methyl-2-phenylpyrimido[4,5-b]quinolin-4(10H)-one
  参考文献：
  名称：

  Antitumor studies. Part 1: Design, synthesis, antitumor activity, and AutoDock study of 2-deoxo-2-phenyl-5-deazaflavins and 2-deoxo-2-phenylflavin-5-oxides as a new class of antitumor agents

  摘要：

  Novel 2-deoxo-2-phenyl-5-deazaflavins and 2-deoxo-2-phenylflavin-5-oxides were prepared as a new class of antitumor agents and showed significant antitumor activities against NCI-H 460, HCT 116, A 431, CCRF-HSB-2, and KB cell lines. In vivo investigation, 2-deoxo-10-methyl-2-phenyl-5-deazaflavin exhibited the effective antitumor activity against A 431 human adenocarcinoma cells transplanted subcutaneously into nude mouse. Furthermore, AutoDock study has been done by binding of the flavin analogs into PTK pp60(c-src), where a good correlation between their IC50 and AutoDock binding free energy was exhibited. In particular, 2-deoxo-2-phenylflavin-5-oxides exhibited the highest potential binding affinity within the binding pocket of PTK. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.063
• 作为产物：
  描述：

  6-anilino-4-methylthio-2-phenylpyrimidine-5-carboxaldehyde 在 PPA 作用下， 反应 2.0h， 以60%的产率得到2-phenylpyrimido[4,5-b]quinolin-4(3H)-one
  参考文献：
  名称：

  Kohra, Shinya; Tominaga, Yoshinori; Hosomi, Akira, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 959 - 968

  摘要：

  DOI：

文献信息

• <i>ortho</i>-Naphthoquinone-catalyzed aerobic oxidation of amines to fused pyrimidin-4(3<i>H</i>)-ones: a convergent synthetic route to bouchardatine and sildenafil
  作者：Kyeongha Kim、Hun Young Kim、Kyungsoo Oh

  DOI：10.1039/d0ra06820a

  日期：——

  A facile access to fused pyrimidin-4(3H)-one derivatives has been established by using the metal-free ortho-naphthoquinone-catalyzed aerobic cross-coupling reactions of amines. The utilization of two readily available amines allowed a direct coupling strategy to quinazolinone natural product, bouchardatine, as well as sildenafil (Viagra™) in a highly convergent manner.

  通过使用无金属邻萘醌催化的胺有氧交叉偶联反应，已经建立了一种容易获得稠合 pyrimidin-4(3 H )-one 衍生物的方法。利用两种容易获得的胺，可以以高度收敛的方式直接偶联喹唑啉酮天然产物布沙达汀和西地那非 (Viagra™)。
• Copper-catalyzed cascade reaction: synthesis of pyrimido[4,5-<i>b</i>]quinolinones from 2-chloroquinoline-3-carbonitriles with (aryl)methanamines
  作者：Jay Bahadur Singh、Kalpana Mishra、Tanu Gupta、Radhey M. Singh

  DOI：10.1039/c7nj04689h

  日期：——

  of 2-chloroquinoline-3-carbonitriles with benzyl amines and sodium hydroxide in aerobic atmosphere has been developed for the synthesis of pyrimido[4,5-b]quinoline-4-ones. The reaction proceeds sequentially via Ullmann-coupling and conversion of nitrile to amide followed by nucleophilic addition of amide nitrogen onto iminium carbon and air oxidation. Reagents and substrates are cheap and easily available/accessible

  在有氧环境下，铜催化2-氯喹啉-3-腈与苄胺和氢氧化钠的级联反应已用于嘧啶并[4,5 - b ]喹啉-4-酮的合成。该反应通过乌尔曼偶合依次进行，并且将腈转化为酰胺，然后将酰胺氮亲核加成到亚胺碳上并进行空气氧化。试剂和底物价格便宜，易于获得/获取。还讨论了合理的反应机理。
• Copper-catalyzed synthesis of quinoline derivatives via tandem Knoevenagel condensation, amination and cyclization
  作者：Shiv Dhiman、Hitesh Kumar Saini、Nitesh Kumar Nandwana、Dalip Kumar、Anil Kumar

  DOI：10.1039/c6ra03798d

  日期：——

  A novel regioselective synthesis of 2-aminoquinolines and 2-arylquinoline-3-carbonitriles is described via copper-mediated tandem reaction. Formation of substituted quinolines involves Knoevenagel condensation of ortho-bromobenzaldehyde with active methylene nitriles followed by copper-catalyzed reductive amination and intramolecular cyclization.

  通过铜介导的串联反应描述了2-氨基喹啉和2-芳基喹啉-3-腈的新的区域选择性合成。取代喹啉的形成涉及邻溴苯甲醛与活性亚甲基腈的Knoevenagel缩合，然后进行铜催化的还原胺化和分子内环化。
• Synthesis of 2-Aminoquinoline-3-carboamides and Pyrimido[4,5-<i>b</i>]quinolin-4-ones through Copper-Catalyzed One-pot Multicomponent Reactions
  作者：Xin-Ying Zhang、Xiao-Jie Guo、Xue-Sen Fan

  DOI：10.1002/asia.201402962

  日期：2015.1

  compounds display remarkable antimicrobial, anti‐inflammatory, antitumor, antiallergy, analgesic, and antioxidant activities. The importance of pyrimido[4,5‐b]quinolinones has stimulated enormous efforts to develop efficient methodologies for their synthesis. Herein, we disclose a novel synthetic protocol toward pyrimido[4,5‐b]quinolin‐4‐ones through Cu(OAc)2‐catalyzed one‐pot four‐component reactions

  嘧啶并[4,5- b ]喹啉酮，吸引从化学和药物科学家相当大的兴趣，因为这些化合物显示显着的抗微生物剂，消炎，抗肿瘤，抗过敏，镇痛，和抗氧化活性。嘧啶并[4,5- b ]喹啉酮的重要性激发了巨大的努力，以开发有效的合成方法。在这里，我们公开了一种通过Cu（OAc）2对嘧啶基[4,5 - b ]喹啉-4-酮合成的新型合成方案2-溴苯甲醛，氨水，氰基乙酰胺和醛的催化一锅四组分反应。该合成程序将胺化/缩合/环化/脱氢反应结合在一个罐中，从而允许以简单实用的方式合成复杂的化合物。与文献方法相比，本文开发的合成策略显示出以下优点：容易获得且在经济上可持续的起始原料，产品的结构多样性，良好的官能团耐受性和非常简单的操作过程。
• KOHRA, SHINYA;TOMINAGA, YOSHINORI;HOSOMI, AKIRA, J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 959-968
  作者：KOHRA, SHINYA、TOMINAGA, YOSHINORI、HOSOMI, AKIRA

  DOI：——

  日期：——