2-deoxo-10-ethyl-2-phenyl-5-deazaflavin | 77778-26-8

• 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: 2-deoxo-10-ethyl-2-phenyl-5-deazaflavin
• 英文别名: 10-ethyl-2-phenylpyrimido[4,5-b]quinolin-4(10H)-one；10-Ethyl-2-phenylpyrimido[4,5-b]quinolin-4-one
• CAS: 77778-26-8
• 化学式: C₁₉H₁₅N₃O
• 分子量: 301.348
• InChiKey: OJCCBHSBWUYJBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  45
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  辛胺 、 2-deoxo-10-ethyl-2-phenyl-5-deazaflavin 在 三乙胺 作用下， 以49%的产率得到10-ethyl-5-(n-octylamino)-2-phenylpyrimido[4,5-b]quinolin-4(10H)-one
  参考文献：
  名称：

  Antitumor studies. Part 5: Synthesis, antitumor activity, and molecular docking study of 5-(monosubstituted amino)-2-deoxo-2-phenyl-5-deazaflavins

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.09.022
• 作为产物：
  描述：

  2-苯基-6-氯-4-羟基嘧啶 在 三氯氧磷 作用下， 反应 7.0h， 生成 2-deoxo-10-ethyl-2-phenyl-5-deazaflavin
  参考文献：
  名称：

  Syntheses of 2-deoxo-2-phenyl-5-deazaflavins and 3-phenyl-5-deazaflavins and their use in the oxidation of benzyl alcohol and benzylamine.

  摘要：

  将 6-氯-2-苯基嘧啶-4 (3H)-酮与 N-烷基苯胺缩合制备的 6-(N-烷基苯胺)-2-苯基嘧啶-4 (3H)-酮用维尔斯梅尔试剂（二甲基甲酰胺-磷酰氯）处理，可以得到相应的 10-烷基-2-脱氧-2-苯基-5-脱氮黄素（III），产量极高。将 6-氯-5-甲酰基-3-苯基脲嘧啶与 N-烷基苯胺在二甲基甲酰胺中加热，只需一步就能得到相应的 10-烷基-3-苯基-5-去氮黄素（VI）。比较了由此得到的 5-脱氮黄素（III）和（VI）氧化苄醇和苄胺的能力，并观察到氧化反应的一些自动循环。化合物 III 与苄胺的反应特别生成了加合物 5-苄氨基-2-脱氧-2-苯基-5-脱氮黄素。

  DOI：

  10.1248/cpb.28.3514

文献信息

• 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
  作者：Hamed I. Ali、Keiichiro Tomita、Eiichi Akaho、Hiroto Kambara、Shinji Miura、Hiroyuki Hayakawa、Noriyuki Ashida、Yutaka Kawashima、Takehiro Yamagishi、Hisao Ikeya

  DOI：10.1016/j.bmc.2006.09.063

  日期：2007.1.1

  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.