2-methyl-N-(2-methyl-5,8-dioxoquinolin-7-yl)propanamide | 162219-41-2

• 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-N-(2-methyl-5,8-dioxoquinolin-7-yl)propanamide
• CAS: 162219-41-2
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: WRQCMDFGGMWRLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-N-(2-methyl-5,8-dioxoquinolin-7-yl)propanamide 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 48.25h， 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：

  5,7-二硝基-2-甲基-8-喹啉醇 在 palladium on activated charcoal 盐酸 、 甲醇 、 potassium dichromate 、 氢气 、 sodium acetate 、 溶剂黄146 、 sodium sulfite 作用下， 5.0 ℃ 、206.84 kPa 条件下， 反应 19.0h， 生成 2-methyl-N-(2-methyl-5,8-dioxoquinolin-7-yl)propanamide
  参考文献：
  名称：

  Lavendamycin甲基酯和相关新型喹啉二酮的高效实用合成方法。

  摘要：

  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。

  DOI：

  10.1021/jo960794t

文献信息

• Synthesis and evaluation of antitumor activity of novel N-acyllavendamycin analogues and quinoline-5,8-diones
  作者：Mohammad Behforouz、Wen Cai、Farahnaz Mohammadi、Mark G. Stocksdale、Zhengxiang Gu、Mohammad Ahmadian、Darric E. Baty、Michele R. Etling、Charmaine H. Al-Anzi、Tyson M. Swiftney

  DOI：10.1016/j.bmc.2006.09.039

  日期：2007.1.1

  A series of 7-N-acyllavendamycins with zero, one or two substituents at the C-2', C-3', and C-11' were synthesized through short and efficient methods. Pictet-Spengler condensation of 7-N-acylamino-2-formylquinoline-5,8-diones with tryptamine or tryptophans produced the desired lavendamycins. Screening data on a panel of three ras oncogene-transformed cell lines and the non-transformed parent cell line showed that a significant number of these analogues are potent antitumor agents and appear to be particularly active against K-ras transformed cells. Compared with the corresponding quinolinediones, these novel lavendamycins are much more inhibitory toward the transformed cells indicating that the P-carboline moiety of the lavendamycin analogues plays an important role in its potency and selective toxicity. (c) 2006 Elsevier Ltd. All rights reserved.
• 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。
• Chemistry of Quinoline-5,8-diones
  作者：Mohammad Behforouz、Jalal Haddad、Wen Cai、Zhengxiang Gu

  DOI：10.1021/jo971823i

  日期：1998.1.1

  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.