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