2-methyl-5,8-dioxo-5,8-dihydroquinoline-7-amine | 180208-48-4

• 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: 2-methyl-5,8-dioxo-5,8-dihydroquinoline-7-amine
• 英文别名: 7-amino-2-methylquinoline-5,8-dione
• CAS: 180208-48-4
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: SDMIHCWUTXPJKV-UHFFFAOYSA-N

物化性质

• 熔点：
  224-225 °C
• 沸点：
  390.4±42.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-5,8-dioxo-5,8-dihydroquinoline-7-amine 在 硫酸 作用下， 反应 24.25h， 生成 7-methoxy-2-methylquinoline-5,8-dione
  参考文献：
  名称：

  Chemistry of Quinoline-5,8-diones

  摘要：

  Room-temperature acid-catalyzed methanolysis of 7-formamido-, 7-acetamido-, or 7-isobutyramido-2-methylquinoline-5,8-diones (3, 4, 5) gives go od to excellent yields of 7-amino-2-methylquinoline-5,8-dione(6). Simple methods for the synthesis of novel 7-amino-6-chloro-2-methylquinoline-5,8-dione (7), 7-alkoxy-2-methylquinoline-5,8-diones (9-11), and quinoline quinols (12, 13) are described, and the corresponding mechanisms are discussed. The replacement of an amino group on a quinone ring by alkoxy groups to produce 9-11 is reported for the first time and offers easy routes for the syntheses of these alkoxy derivatives. Also, the 1,2-addition of an ethyl group (rather than the expected 1,4-addition of a cyano group) of the reagent diethylaluminum cyanide to a quinolinedione is another novel reaction for the efficient preparation of quinoline quinols 12 and 13. An easy transformation of amino compound 6 to its acetamido derivative 4 is also described.

  DOI：

  10.1021/jo971823i
• 作为产物：
  描述：

  6,7-二溴-2-甲基喹啉-5,8-二酮 在 氨 、 氢溴酸 、 三乙胺 、 苯胺 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 2-methyl-5,8-dioxo-5,8-dihydroquinoline-7-amine
  参考文献：
  名称：

  制备7-烷基氨基-2-甲基喹啉-5，8-二酮。

  摘要：

  通过Skraup反应，在5个步骤中由2,5-二甲氧基苯胺合成了几种新颖的7-烷基氨基-2-甲基喹啉-5,8-二酮（2），然后进行去甲基化，氧化溴化，胺化和脱溴。我们已经实现了几种6-溴-7-烷基氨基-2-甲基喹啉-5,8-二酮的不寻常的氢溴酸催化的脱溴反应，从而以良好的收率得到了7-烷基氨基-2-甲基喹啉-5,8-二酮。

  DOI：

  10.1021/jo0257039
• 作为试剂：
  描述：

  亚磷酸二乙酯 在 sodium hydride 、 2-methyl-5,8-dioxo-5,8-dihydroquinoline-7-amine 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.0h， 以54%的产率得到1,1,2,2-四乙氧基二膦1,2-二氧化物
  参考文献：
  名称：

  喹啉-5,8-二酮与选定带电磷亲核试剂的反应

  摘要：

  摘要 两种喹啉-5,8-二酮衍生物——2-methyl-5,8-dioxo-5,8-dihydroquinoline-7-amine (2a) 和 N-(2-methyl-5,8-二氧-5,8-二氢喹啉-7-基）乙酰胺（2b）—已通过它们与带负电荷的三配位磷亲核试剂的反应得到证明，例如R2P-YM（1a-d，Y = O或孤对；R = Ph、tBu、OCH2CMe2CH2O 或 EtO；M = Li 或 Na）。1a-d 参与到 2a 和 2b 的单电子转移 (SET)，分别产生自由基阴离子 3 和 4，以及 R2P(= Y)·(5) 型的短寿命磷中心自由基中间体。自由基 5 二聚化得到 R2P(Y)–(Y)PR2 (6)。3 和 4 在 300 K 的 THF（四氢呋喃）中的半衰期都超过 1 个月。

  DOI：

  10.1080/10426507.2011.626472

文献信息

• Lavendamycin analogues and methods of synthesizing and using lavendamycin analogues
  申请人：Behforouz Mohammad

  公开号：US20060079497A1

  公开（公告）日：2006-04-13

  Lavendamycin analogues, methods for their synthesis, and methods for their use in the treatment of diseases such as cancer and HIV infection are described.

  Lavendamycin类似物，其合成方法，以及在治疗癌症和HIV感染等疾病中使用的方法被描述。
• Simple preparation of 7-alkylamino-2-methylquinoline-5,8-diones: regiochemistry in nucleophilic substitution reactions of the 6- or 7-bromo-2-methylquinoline-5,8-dione with amines
  作者：Han Young Choi、Dae Yoon Chi

  DOI：10.1016/j.tet.2004.04.041

  日期：2004.5

  7-Alkylamino-2-methylquinoline-5,8-diones (7) were prepared from 6-bromo-2-methylquinoline-5,8-dione (2) not from 7-bromo-2-methylquinoline-5,8-dione (1). The chemistry of the transformation of 6-bromo-2-methylquinoline-5,8-dione (2) and various alkylamines, such as piperidine, 2-methylaziridine, benzylamine, n-butylamine, cyclohexylamine, t-butylamine, and ammonia, to 7-alkylamino compounds 7 as well

  由6-溴-2-甲基喹啉-5,8-二酮（2）而不是由7-溴-2-甲基喹啉-5,8-二酮制备7-烷基氨基-2-甲基喹啉-5,8-二酮（7）（1）。6-溴-2-甲基喹啉-5,8-二酮（2）和各种烷基胺（如哌啶，2-甲基氮丙啶，苄胺，正丁胺，环己胺，叔丁胺和氨）的化学转化7-烷基氨基化合物7以及7-溴化合物1和烷基胺向6-烷基氨基-2-甲基喹啉-5,8-二酮的转化11被研究了。由5,8-二羟基-2-甲基喹啉（15）和5,7形成的关键中间体6和7-溴-2-甲基-2-甲基喹啉-5,8-二酮（2和1）的高效简单合成路线分别开发了-二溴-8-羟基-2-甲基喹啉（9）。我们还提出了6-和7-溴-2-甲基喹啉-5,8-二酮（2和1）的亲核胺基反应具有非正常区域选择性的机制。
• Highly Efficient and Practical Syntheses of Lavendamycin Methyl Ester and Related Novel Quinolindiones
  作者：Mohammad Behforouz、Jalal Haddad、Wen Cai、Macklin B. Arnold、Farahnaz Mohammadi、Aron C. Sousa、Mark A. Horn

  DOI：10.1021/jo960794t

  日期：1996.1.1

  afforded the novel 7-aminoquinoline-5,8-dione 7 in excellent yields. Due to our efficient preparation of dione 14a, we now report a short and practical method for the total synthesis of the potent antitumor agent lavendamycin methyl ester (1b) with an excellent overall yield.

  新型的7-（N-甲酰基-，7-（N-乙酰基-氨基和7-（N-异丁酰氨基）-2-甲基喹啉-5,8-二酮）通过硝化三氯甲烷的三步合成法以优异的总收率合成市售8-羟基-2-甲基喹啉，然后进行还原酰化步骤，然后氧化7-（N-乙酰氨基）-2-甲基喹啉-5,8-二酮（14a）的酸水解得到了新型7-氨基喹啉- 5,8-dione 7的收率很高由于我们高效地制备了dione 14a，我们现在报告了一种短而实用的方法，可以有效地合成有效的抗肿瘤药物拉达霉素甲酯（1b），且总收率很高。
• Investigating the antiproliferative activity of quinoline-5,8-diones and styrylquinolinecarboxylic acids on tumor cell lines
  作者：B. Podeszwa、H. Niedbala、J. Polanski、R. Musiol、D. Tabak、J. Finster、K. Serafin、M. Milczarek、J. Wietrzyk、S. Boryczka、W. Mol、J. Jampilek、J. Dohnal、D.S. Kalinowski、D.R. Richardson

  DOI：10.1016/j.bmcl.2007.09.040

  日期：2007.11

  The structure-activity relationships of new quinoline based compounds were investigated. Quinoline-5,8-dione and styrylquinoline scaffolds were used for the design of potentially active compounds. The novel analogues had comparable antiproliferative activity to cisplatin when evaluated in a bioassay against the P388 leukemia cell line. However, these compounds appeared far less efficient against SK-N-MC neuroepithelioma cells. Analogues without the 5,8-dione structure but containing the 8-carboxylic acid group were also found to induce antiproliferative activity. Hydrophobicity as measured by HPLC did not correlate with antiproliferative activity. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis, spectroscopy and computational studies of some novel phosphorylated derivatives of quinoline-5,8-diones
  作者：Jacek E. Nycz、Grzegorz Malecki、Lukasz Ponikiewski、Markus Leboschka、Maria Nowak、Joachim Kusz

  DOI：10.1016/j.molstruc.2010.11.032

  日期：2011.2

  The neutral phosphorus nucleophiles such as R2P(=Y)M [1a-f, Y=O or lone pair; R = Ph, tBu, OCH2C(CH3)(2) CH2O, (PrO)-O-i, EtO or MeO: M = H or SiMe3] allowed the radical addition to 2-methyl-5,8-dioxo-5,8-dihydroquinoline-7-amine (2a) and N-(2-methyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamide (2b) giving exclusively O-phosphorylated products, i.e.: 7-acetylamino-5-hydroxy-2-methylquinolin-8-yl diphenylphosphinate (3a), 7-acetylamino-5-hydroxy-2-methylquinolin-8-yl-tbutylphenylphosphinate (3b), 7-acetylamino-5-hydroxy-2-methylquinolin-8-yl diisopropyl phosphate (3c), 7-acetylamino-5-hydroxy-2-methylquinolin-8-yl diethyl phosphate (3d), N-(8-[(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2yl)oxy]-5-hydroxy-2-methylquinolin-7-yl)acetamide (3e), 7-amino-5-hydroxy-2-methylquinolin-8-yl dimethyl phosphate (3f) and 7-amino-5-hydroxy-2-methylquinolin-8-yl-tbutylphenylphosphinate (3g), respectively, with high yield. All products were quantitatively prepared and characterized by microanalysis, and multinuclear NMR spectroscopy. Seven of them, i.e.: 2a, 2b, 3a, 3b, 3d, 3e and 3g have been characterized by single crystal X-ray diffraction method. The geometries of the studied compounds were optimized in singlet states using the density functional theory (DFT) method with B3LYP functional. The redox properties of 2a and 2b have been studied using cyclic voltammetry. The reduction corresponds to the electrochemical behaviour of naturally occurring quinones. (C) 2010 Elsevier B.V. All rights reserved.