7-formamido-2-methylquinoline-5,8-dione | 180208-52-0

• 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: 7-formamido-2-methylquinoline-5,8-dione
• 英文别名: N-(2-methyl-5,8-dioxoquinolin-7-yl)formamide
• CAS: 180208-52-0
• 化学式: C₁₁H₈N₂O₃
• 分子量: 216.196
• InChiKey: XWGGEPNVFRGSPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  7-formamido-2-methylquinoline-5,8-dione 在 盐酸 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 24.33h， 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 、 potassium dichromate 、 氢气 、 sodium formate 、 溶剂黄146 、 sodium sulfite 作用下， 以 水 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 18.17h， 生成 7-formamido-2-methylquinoline-5,8-dione
  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, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents
  作者：Wen Cai、Mary Hassani、Rajesh Karki、Ervin D. Walter、Katherine H. Koelsch、Hassan Seradj、Jayana P. Lineswala、Hamid Mirzaei、Jeremy S. York、Fatemeh Olang、Minoo Sedighi、Jennifer S. Lucas、Thomas J. Eads、Anthony S. Rose、Sahba Charkhzarrin、Nicholas G. Hermann、Howard D. Beall、Mohammad Behforouz

  DOI：10.1016/j.bmc.2010.01.037

  日期：2010.3

  A series of lavendamycin analogues with two, three or four substituents at the C-6, C-7 N, C-2', C-3' and C-11' positions were synthesized via short and efficient methods and evaluated as potential NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor agents. The compounds were prepared through Pictet-Spengler condensation of the desired 2-formylquinoline-5,8-diones with the required tryptophans followed by further needed transformations. Metabolism and toxicity studies demonstrated that the best substrates for NQO1 were also the most selectively toxic to NQO1-rich tumor cells compared to NQO1-deficient tumor cells. (C) 2010 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.