2-(3-methylthiophen-2-yl)-1H-imidazo[4,5-b]phenazine | 1254984-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(3-methylthiophen-2-yl)-1H-imidazo[4,5-b]phenazine
• CAS: 1254984-04-7
• 化学式: C₁₈H₁₂N₄S
• 分子量: 316.386
• InChiKey: FEGYRAVLBHVOGO-UHFFFAOYSA-N

物化性质

• 熔点：
  284 °C
• 沸点：
  616.9±63.0 °C(predicted)
• 密度：
  1.432±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.46
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-甲基噻吩醛 、 2,3-二氨基吩嗪 在 sodium metabisulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以90%的产率得到2-(3-methylthiophen-2-yl)-1H-imidazo[4,5-b]phenazine
  参考文献：
  名称：

  Conventional and microwave-assisted synthesis of imidazole and guanidine derivatives and their biological evaluation

  摘要：

  A number of imidazole derivatives 3a-f and 4a-f have been synthesized by the condensation of 3-methylthiophen-2-carboxaldehyde 1a, 5-methylthiophen-2-carboxaldehyde 1b, N-methylpyrrol-2-carboxaldehyde 1c, 1-naphthaldehyde 1d, 2-naphthaldehyde 1e, and 2-hydroxy-1-naphthaldehyde 1f with 1,2-diaminoanthraquinone 2a and 2,3-diaminophenazine 2b, respectively. Condensation of 2-guanidinobenzimidazole with functionalized aldehydes 1a-f leads to the formation of guanidine derivatives 5a-f. Both imidazole (3a-f, 4a-f) and guanidine derivatives (5a-f) were synthesized in good yields using conventional heating and microwave irradiation techniques. Structures assigned to compounds 3a-f, 4a-f and 5a-f are supported by correct spectral and analytic data. On screening for anti-inflammatory and anticancer activities, compounds 3e, 4a and 5a exhibited good anti-inflammatory and compounds 3d, 3f, 4d and 4f showed very good anticancer activity.

  DOI：

  10.1007/s00044-010-9410-6

文献信息

• Conventional and microwave-assisted synthesis of imidazole and guanidine derivatives and their biological evaluation
  作者：Sham M. Sondhi、Jaiveer Singh、Partha Roy、S. K. Agrawal、A. K. Saxena

  DOI：10.1007/s00044-010-9410-6

  日期：2011.9

  A number of imidazole derivatives 3a-f and 4a-f have been synthesized by the condensation of 3-methylthiophen-2-carboxaldehyde 1a, 5-methylthiophen-2-carboxaldehyde 1b, N-methylpyrrol-2-carboxaldehyde 1c, 1-naphthaldehyde 1d, 2-naphthaldehyde 1e, and 2-hydroxy-1-naphthaldehyde 1f with 1,2-diaminoanthraquinone 2a and 2,3-diaminophenazine 2b, respectively. Condensation of 2-guanidinobenzimidazole with functionalized aldehydes 1a-f leads to the formation of guanidine derivatives 5a-f. Both imidazole (3a-f, 4a-f) and guanidine derivatives (5a-f) were synthesized in good yields using conventional heating and microwave irradiation techniques. Structures assigned to compounds 3a-f, 4a-f and 5a-f are supported by correct spectral and analytic data. On screening for anti-inflammatory and anticancer activities, compounds 3e, 4a and 5a exhibited good anti-inflammatory and compounds 3d, 3f, 4d and 4f showed very good anticancer activity.