6-(N-ethyl-4-methylanilino)-2-phenylpyrimidin-4(3H)-one | 917384-40-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-(N-ethyl-4-methylanilino)-2-phenylpyrimidin-4(3H)-one
• CAS: 917384-40-8
• 化学式: C₁₉H₁₉N₃O
• 分子量: 305.379
• InChiKey: MNDLDUOAURIGFA-UHFFFAOYSA-N

物化性质

• 沸点：
  456.7±55.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  48.99
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-(N-ethyl-4-methylanilino)-2-phenylpyrimidin-4(3H)-one 在 溶剂黄146 、 sodium nitrite 作用下， 以77%的产率得到10-ethyl-4,10-dihydro-7-methyl-4-oxo-2-phenylbenzo[g]pteridin-5-oxide
  参考文献：
  名称：

  Antitumor studies. Part 1: Design, synthesis, antitumor activity, and AutoDock study of 2-deoxo-2-phenyl-5-deazaflavins and 2-deoxo-2-phenylflavin-5-oxides as a new class of antitumor agents

  摘要：

  Novel 2-deoxo-2-phenyl-5-deazaflavins and 2-deoxo-2-phenylflavin-5-oxides were prepared as a new class of antitumor agents and showed significant antitumor activities against NCI-H 460, HCT 116, A 431, CCRF-HSB-2, and KB cell lines. In vivo investigation, 2-deoxo-10-methyl-2-phenyl-5-deazaflavin exhibited the effective antitumor activity against A 431 human adenocarcinoma cells transplanted subcutaneously into nude mouse. Furthermore, AutoDock study has been done by binding of the flavin analogs into PTK pp60(c-src), where a good correlation between their IC50 and AutoDock binding free energy was exhibited. In particular, 2-deoxo-2-phenylflavin-5-oxides exhibited the highest potential binding affinity within the binding pocket of PTK. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.063
• 作为产物：
  描述：

  N-乙基对甲苯胺 、 2-苯基-6-氯-4-羟基嘧啶 以92%的产率得到6-(N-ethyl-4-methylanilino)-2-phenylpyrimidin-4(3H)-one
  参考文献：
  名称：

  Antitumor studies. Part 1: Design, synthesis, antitumor activity, and AutoDock study of 2-deoxo-2-phenyl-5-deazaflavins and 2-deoxo-2-phenylflavin-5-oxides as a new class of antitumor agents

  摘要：

  Novel 2-deoxo-2-phenyl-5-deazaflavins and 2-deoxo-2-phenylflavin-5-oxides were prepared as a new class of antitumor agents and showed significant antitumor activities against NCI-H 460, HCT 116, A 431, CCRF-HSB-2, and KB cell lines. In vivo investigation, 2-deoxo-10-methyl-2-phenyl-5-deazaflavin exhibited the effective antitumor activity against A 431 human adenocarcinoma cells transplanted subcutaneously into nude mouse. Furthermore, AutoDock study has been done by binding of the flavin analogs into PTK pp60(c-src), where a good correlation between their IC50 and AutoDock binding free energy was exhibited. In particular, 2-deoxo-2-phenylflavin-5-oxides exhibited the highest potential binding affinity within the binding pocket of PTK. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.063

文献信息

• Antitumor studies. Part 5: Synthesis, antitumor activity, and molecular docking study of 5-(monosubstituted amino)-2-deoxo-2-phenyl-5-deazaflavins
  作者：Ajaya R. Shrestha、Hamed I. Ali、Noriyuki Ashida、Tomohisa Nagamatsu

  DOI：10.1016/j.bmc.2008.09.022

  日期：2008.10

  Various novel 5-( monosubstituted amino)-2-deoxo-2-phenyl-5-deazaflavins derivatives have been synthesized by direct coupling of 5-deazaflavins and N-alkyl or aryl amines. The antitumor activities against human tumor cell lines CCRF-HSB-2 and KB cells have been investigated in vitro and many compounds showed promising potential antitumor activities with less cytotoxicities. AutoDock molecular docking into PTK ( PDB code: 1t46) has been done for lead optimization of these compounds as potential PTK inhibitors. Some of the synthesized 5-( monosubstituted amino)-2-deoxo-2-phenyl-5-deazaflavins at the 5- position exhibited reasonable binding affinities into PTK with the hydrogen bond through their C5-NH moiety. (C) 2008 Elsevier Ltd. All rights reserved.