ethyl 3-aminothiazolo[3,2-a]benzimidazole-2-carboxylate | 1229123-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: ethyl 3-aminothiazolo[3,2-a]benzimidazole-2-carboxylate
• 英文别名: Ethyl 1-amino-[1,3]thiazolo[3,2-a]benzimidazole-2-carboxylate
• CAS: 1229123-72-1
• 化学式: C₁₂H₁₁N₃O₂S
• 分子量: 261.304
• InChiKey: IIAVJYOIHPONRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-(1H-benzimidazol-2-ylsulfanyl)-2-cyanoacetate 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 ethyl 3-aminothiazolo[3,2-a]benzimidazole-2-carboxylate
  参考文献：
  名称：

  Cell cycle disruption and apoptotic activity of 3-aminothiazolo[3,2-a]benzimidazole-2-carbonitrile and its homologues

  摘要：

  3-Aminothiazolo[3,2-a]benzimidazole-2-carbonitrile (2) was prepared and upon hydrolysis using concentrated sulfuric acid or phosphoric acid resulted in the corresponding 3-aminothiazolo[3,2-a] benzimidazole-2-carboxamide derivative (3). Cyclization of the 2 using acetic anhydride or formic acid gave the corresponding pyrimido[4',5' 4,5]thiazolo[3,2-a]benzimidazol-4(3H)-one (5) in good yields. Acetylation of 2 with acetic anhydride in pyridine afforded N-acetylaminothiazolo[3,2-a]benzimidazole-2-carbonitrile (6). In vitro annproliferative activities of synthesized compounds were investigated at The National Cancer Institute (NCI), USA, according to their applied protocol. Compound 6 revealed significant annproliferative activity, however, weak activity was shown by the other derivatives. Cell cycle disruption and apoptotic activity of 6 were studied, interestingly, 6 has the ability to arrest G2/M phase and it can induce apoptosis in time dependant manner.

  DOI：

  10.1016/j.ejmech.2010.02.025

文献信息

• Cell cycle disruption and apoptotic activity of 3-aminothiazolo[3,2-a]benzimidazole-2-carbonitrile and its homologues
  作者：Abdelwareth A.O. Sarhan、Abdullah Al-Dhfyan、Maha A. Al-Mozaini、Chaker N. Adra、Tarek Aboul-Fadl

  DOI：10.1016/j.ejmech.2010.02.025

  日期：2010.6

  3-Aminothiazolo[3,2-a]benzimidazole-2-carbonitrile (2) was prepared and upon hydrolysis using concentrated sulfuric acid or phosphoric acid resulted in the corresponding 3-aminothiazolo[3,2-a] benzimidazole-2-carboxamide derivative (3). Cyclization of the 2 using acetic anhydride or formic acid gave the corresponding pyrimido[4',5' 4,5]thiazolo[3,2-a]benzimidazol-4(3H)-one (5) in good yields. Acetylation of 2 with acetic anhydride in pyridine afforded N-acetylaminothiazolo[3,2-a]benzimidazole-2-carbonitrile (6). In vitro annproliferative activities of synthesized compounds were investigated at The National Cancer Institute (NCI), USA, according to their applied protocol. Compound 6 revealed significant annproliferative activity, however, weak activity was shown by the other derivatives. Cell cycle disruption and apoptotic activity of 6 were studied, interestingly, 6 has the ability to arrest G2/M phase and it can induce apoptosis in time dependant manner.