7-N-acetyldemethyllavendamycin n-propyl ester | 1226517-43-6

• 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-acetyldemethyllavendamycin n-propyl ester
• 英文别名: propyl 1-(7-acetamido-5,8-dioxoquinolin-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1226517-43-6
• 化学式: C₂₆H₂₀N₄O₅
• 分子量: 468.469
• InChiKey: LWPUXZWHLGJOAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Tryptophan-n-propylester 、 N-(2-甲酰基-5,8-二氧代-5,8-二氢喹啉-7-基)乙酰胺 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 4.0h， 以30%的产率得到7-N-acetyldemethyllavendamycin n-propyl 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

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.