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

• Syntheses of 2-deoxo-2-phenyl-5-deazaflavins and 3-phenyl-5-deazaflavins and their use in the oxidation of benzyl alcohol and benzylamine.
  作者：FUMIO YONEDA、KENYA MORI、MASAMI ONO、YOKO KADOKAWA、ETSUKO NAGAO、HIROYUKI YAMAGUCHI

  DOI：10.1248/cpb.28.3514

  日期：——

  Treatment of 6-(N-alkylanilino)-2-phenylpyrimidin-4 (3H)-ones, which were prepared by the condensation of 6-chloro-2-phenylpyrimidin-4 (3H)-one with N-alkylanilines, with the Vilsmeier reagent (dimethylformamide-phosphoryl chloride) gave the corresponding 10-alkyl-2-deoxo-2-phenyl-5-deazaflavins (III) in excellent yields. Heating of 6-chloro-5-formyl-3-phenyluracil with N-alkylanilines in dimethylformamide gave the corresponding 10-alkyl-3-phenyl-5-deazaflavins (VI) in a single step. The abilities of the 5-deazaflavins (III) and (VI) thus obtained to oxidize benzyl alcohol and benzylamine were compared, and some automatic recycling of the oxidation reactions was observed. The reaction of compounds III with benzylamine exceptionally gave the adducts, 5-benzylamino-2-deoxo-2-phenyl-5-deazaflavins.

  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。
• 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.
• 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.