7-N-acetyldemethyllavendmycin N-benzylpiperazine amide | 1226517-44-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 7-N-acetyldemethyllavendmycin N-benzylpiperazine amide
• 英文别名: N-[2-[3-(4-benzylpiperazine-1-carbonyl)-9H-pyrido[3,4-b]indol-1-yl]-5,8-dioxoquinolin-7-yl]acetamide
• CAS: 1226517-44-7
• 化学式: C₃₄H₂₈N₆O₄
• 分子量: 584.634
• InChiKey: KZZJGQHANGCMOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  44
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tryptophan N-benzylpiperazine amide 、 N-(2-甲酰基-5,8-二氧代-5,8-二氢喹啉-7-基)乙酰胺 在 吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯甲醚 、 四氢呋喃 为溶剂， 反应 30.5h， 以40%的产率得到7-N-acetyldemethyllavendmycin N-benzylpiperazine amide
  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