3-aminothiazolo[3,2-a]benzimidazole-2-carbonitrile | 174621-79-5

• 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: 3-aminothiazolo[3,2-a]benzimidazole-2-carbonitrile
• 英文别名: 1-amino-[1,3]thiazolo[3,2-a]benzimidazole-2-carbonitrile
• CAS: 174621-79-5
• 化学式: C₁₀H₆N₄S
• 分子量: 214.25
• InChiKey: JIWZWBIREBPIAB-UHFFFAOYSA-N

物化性质

• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-aminothiazolo[3,2-a]benzimidazole-2-carbonitrile 在 乙酸酐 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N-(2-Cyano-benzo[4,5]imidazo[2,1-b]thiazol-3-yl)-N'-methyl-formamidine
  参考文献：
  名称：

  Sarhan, A. A. O.; El-Shenef, H. A. H.; Mahmoud, A. M., Journal of Chemical Research, Miniprint, 1996, # 1, p. 116 - 135

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(1H-benzimidazol-2-ylsulfanyl)propanedinitrile 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-aminothiazolo[3,2-a]benzimidazole-2-carbonitrile
  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

• A convenient one-pot synthesis of 2-benzimidazolyl-thioacetophenones and thiazolo[3,2-a]benzimidazoles
  作者：Abd El-Wareth A.O. Sarhan、Hasan A.H. El-Sherief、Abdalla M. Mahmoud

  DOI：10.1016/0040-4020(96)00569-8

  日期：1996.7

  etophenones 3a-d. Which on cyclization yield thiazolo[3,2-a]-benzimidazoles 4a-d. Acetylation of 3a,d gave the N-acetyl derivatives 5a,d. Cyclization of 3a-d or 5d in acetic anhydride or acetic anhydride / pyridine mixture afforded 6a-d. While reaction of 1 with aliphatic or alicyclic ketones gave directly 2,3-disubstituted thiazolo[3,2-a]benzimidazoles 7a-f and 8a-d respectively.

  2-巯基苯并咪唑（1）与芳族酮2a-d在酸化的乙酸中反应，得到2-苯并咪唑基硫代乙酰基苯乙酮3a-d。在环化反应中产生噻唑并[3，2-a]-苯并咪唑4a-d。3a，d的乙酰化得到N-乙酰基衍生物5a，d。3a-d或5d在乙酸酐或乙酸酐/吡啶混合物中的环化得到6a-d。当1与脂族或脂环族酮反应时，分别直接直接得到2，3-二取代的噻唑并[3，2-a]苯并咪唑7a-f和8a-d。
• Sarhan, A. A. O.; Hozien, Z. A.; El-Sherief, H. A. H., Polish Journal of Chemistry, 1995, vol. 69, # 11, p. 1479 - 1483
  作者：Sarhan, A. A. O.、Hozien, Z. A.、El-Sherief, H. A. H.、Mahmoud, A. M.

  DOI：——

  日期：——
• Sarhan, A. A. O.; El-Shenef, H. A. H.; Mahmoud, A. M., Journal of Chemical Research, Miniprint, 1996, # 1, p. 116 - 135
  作者：Sarhan, A. A. O.、El-Shenef, H. A. H.、Mahmoud, A. M.

  DOI：——

  日期：——
• 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.