N-(2-formyl-5,8-dioxoquinolin-7-yl)-2-methylpropanamide | 162219-16-1

• 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: N-(2-formyl-5,8-dioxoquinolin-7-yl)-2-methylpropanamide
• CAS: 162219-16-1
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: ZDQWSOQDMVXPEA-UHFFFAOYSA-N

物化性质

• 熔点：
  183-184 °C
• 沸点：
  551.7±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-formyl-5,8-dioxoquinolin-7-yl)-2-methylpropanamide 、 甲基色氨酸 生成 N-isobutyryldemethyllavendamycin methyl ester
  参考文献：
  名称：

  Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.01.037
• 作为产物：
  描述：

  2-methyl-N-(2-methyl-5,8-dioxoquinolin-7-yl)propanamide 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以75%的产率得到N-(2-formyl-5,8-dioxoquinolin-7-yl)-2-methylpropanamide
  参考文献：
  名称：

  Synthesis and evaluation of antitumor activity of novel N-acyllavendamycin analogues and quinoline-5,8-diones

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2006.09.039

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.
• 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.