4-chloro-5-methyl-2,4-deoxo-5-deazaalloxazine | 383866-67-9

• 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: 4-chloro-5-methyl-2,4-deoxo-5-deazaalloxazine
• 英文别名: 4-chloro-5-methylpyrimido[4,5-b]quinoline
• CAS: 383866-67-9
• 化学式: C₁₂H₈ClN₃
• 分子量: 229.669
• InChiKey: XOFOGDUHCAPOIA-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±25.0 °C(Predicted)
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38.67
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-chloro-5-methyl-2,4-deoxo-5-deazaalloxazine 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 12-methyl-1,2,4-s-triazolo[3',4':6,1]pyrimido[4,5-b]quinoline
  参考文献：
  名称：

  Synthesis, characterization and reactions of 2-deoxo-5-deazaalloxazines

  摘要：

  5-Deazaflavins and their homologues. have been known as potential riboflavin antagonists, bioreductives, and compounds with potent antitumor activity. 2-Amino-4-methylquinoline-3-carbonitrile (2) was prepared as unreported starting material for several interesting 2-deoxo-5-deazalloxazine derivatives. Cyclization of 2 using formamide afforded the 2,4-deoxo-5-deazaalloxazine derivative 7, which was subjected to deamination with nitrous acid to give the 2-deoxo-5-deazaalloxazine (8). The compound 8 was also obtained via 13 by treating the latter with refluxing formic acid or formamide and used as a precursor for synthesis of several 2-deoxo-5-deazaalloxazines 18, 19, 20, 21 and 22. The pharmacological and biological properties of these compounds are still under investigation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00194-8
• 作为产物：
  描述：

  2-amino-4-methylquinoline-3-carboxamide 在 甲酸 、 五氯化磷 、 三氯氧磷 作用下， 反应 6.0h， 生成 4-chloro-5-methyl-2,4-deoxo-5-deazaalloxazine
  参考文献：
  名称：

  Synthesis, characterization and reactions of 2-deoxo-5-deazaalloxazines

  摘要：

  5-Deazaflavins and their homologues. have been known as potential riboflavin antagonists, bioreductives, and compounds with potent antitumor activity. 2-Amino-4-methylquinoline-3-carbonitrile (2) was prepared as unreported starting material for several interesting 2-deoxo-5-deazalloxazine derivatives. Cyclization of 2 using formamide afforded the 2,4-deoxo-5-deazaalloxazine derivative 7, which was subjected to deamination with nitrous acid to give the 2-deoxo-5-deazaalloxazine (8). The compound 8 was also obtained via 13 by treating the latter with refluxing formic acid or formamide and used as a precursor for synthesis of several 2-deoxo-5-deazaalloxazines 18, 19, 20, 21 and 22. The pharmacological and biological properties of these compounds are still under investigation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00194-8