2-deoxo-10-ethyl-2-phenylflavin-5-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 2-deoxo-10-ethyl-2-phenylflavin-5-oxide
• 英文别名: 10-ethyl-4,10-dihydro-4-oxo-2-phenylbenzo[g]pteridin-5-oxide；10-Ethyl-5-oxido-2-phenylbenzo[g]pteridin-5-ium-4-one
• 化学式: C₁₈H₁₄N₄O₂
• 分子量: 318.335
• InChiKey: AHFNAOOCGVKLHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 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：
  73.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-苯基-6-氯-4-羟基嘧啶 在 溶剂黄146 、 sodium nitrite 作用下， 生成 2-deoxo-10-ethyl-2-phenylflavin-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

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.