10-benzyl-2H,3H,4H,10H-pyrimido[4,5-b] quinoline-2,4-di-one | 846028-40-8

• 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: 10-benzyl-2H,3H,4H,10H-pyrimido[4,5-b] quinoline-2,4-di-one
• 英文别名: 10-(Phenylmethyl)pyrimido[4,5-b]quinoline-2,4-dione；10-benzylpyrimido[4,5-b]quinoline-2,4-dione
• CAS: 846028-40-8
• 化学式: C₁₈H₁₃N₃O₂
• 分子量: 303.32
• InChiKey: HXUDVRBCISXVSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N4-benzyl-N4-phenyl-2,4-diamino-6-chloropyrimidine-5-carbaldehyde 在 溶剂黄146 作用下， 反应 0.25h， 以80%的产率得到10-benzyl-2H,3H,4H,10H-pyrimido[4,5-b] quinoline-2,4-di-one
  参考文献：
  名称：

  微波辐射辅助直接合成嘧啶并[4,5- b ]喹啉衍生物

  摘要：

  通过N 4取代的2,4-二氨基-6-氯嘧啶-5-甲醛的微波辅助分子内环化反应，已经制备了几种嘧啶[4,5- b ]喹啉，黄素类似物。该反应在氨基和氯的水解下进行。该方法特别有价值的特征包括更宽的基板范围和操作简便性，以及用于小规模高速合成的更高的安全性。

  DOI：

  10.1016/j.tetlet.2009.12.114

文献信息

• 5-Deazaflavin derivatives as inhibitors of p53 ubiquitination by HDM2
  作者：Michael P. Dickens、Patricia Roxburgh、Andreas Hock、Mokdad Mezna、Barrie Kellam、Karen H. Vousden、Peter M. Fischer

  DOI：10.1016/j.bmc.2013.09.038

  日期：2013.11

  Based on previous reports of certain 5-deazaflavin derivatives being capable of activating the tumour suppressor p53 in cancer cells through inhibition of the p53-specific ubiquitin E3 ligase HDM2, we have conducted an structure-activity relationship (SAR) analysis through systematic modification of the 5-deazaflavin template. This analysis shows that HDM2-inhibitory activity depends on a combination of factors. The most active compounds (e. g., 15) contain a trifluoromethyl or chloro substituent at the deazaflavin C9 position and this activity depends to a large extent on the presence of at least one additional halogen or methyl substituent of the phenyl group at N10. Our SAR results, in combination with the HDM2 RING domain receptor recognition model we present, form the basis for the design of drug-like and potent activators of p53 for potential cancer therapy. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.
• A straightforward synthesis of pyrimido[4,5-b]quinoline derivatives assisted by microwave irradiation
  作者：Jairo Quiroga、Jorge Trilleras、Braulio Insuasty、Rodrigo Abonía、Manuel Nogueras、Antonio Marchal、Justo Cobo

  DOI：10.1016/j.tetlet.2009.12.114

  日期：2010.2

  Several pyrimido[4,5-b]quinolines, flavin analogues, have been prepared by assisted microwave intramolecular cyclization of N4-substituted-2,4-diamino-6-chloropyrimidine-5-carbaldehydes. The reaction takes place with hydrolysis of amino-group and chlorine. Particularly valuable features of this method included the broader substrate scope and operational simplicity as well as increased safety for small-scale

  通过N 4取代的2,4-二氨基-6-氯嘧啶-5-甲醛的微波辅助分子内环化反应，已经制备了几种嘧啶[4,5- b ]喹啉，黄素类似物。该反应在氨基和氯的水解下进行。该方法特别有价值的特征包括更宽的基板范围和操作简便性，以及用于小规模高速合成的更高的安全性。