L-tryptophan sec-butyl ester | 1226517-36-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: L-tryptophan sec-butyl ester
• 英文别名: butan-2-yl (2S)-2-amino-3-(1H-indol-3-yl)propanoate
• CAS: 1226517-36-7
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: AEDFDFXUWFLXAE-HQVZTVAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-tryptophan sec-butyl ester 、 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 16.0h， 以57%的产率得到7-N-acetyldemethyllavendamycin sec-butyl 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：

  仲丁醇 、 L-色氨酸 在 盐酸 、 硫酸 、 碳酸氢钠 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以69%的产率得到L-tryptophan sec-butyl 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

• [EN] COMPOUNDS FOR INHIBITION OF BIOFILMS<br/>[FR] COMPOSÉS POUR L'INHIBITION DE BIOFILMS
  申请人：BURZELL CYNTHIA K

  公开号：WO2013126814A1

  公开（公告）日：2013-08-29

  Disclosed herein are methods of inhibiting biofilm formation, growth or survival comprising administering a compound having the structure (AAA), or a salt, prodrug, tautomer, alternate solid form, non-covalent complex, analog, derivative or combination thereof.