2-(benzo[b]thiophen-3-yl)-1H-imidazole | 1393085-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(benzo[b]thiophen-3-yl)-1H-imidazole
• 英文别名: 2-Benzo[b]thien-3-yl-1H-imidazole；2-(1-benzothiophen-3-yl)-1H-imidazole
• CAS: 1393085-27-2
• 化学式: C₁₁H₈N₂S
• 分子量: 200.264
• InChiKey: QXOKVYIWSVMPQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzo[b]thiophen-3-yl)-1H-imidazole 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.33h， 生成 (2-(benzo[b]thiophen-3-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Discovery of Novel 2-Aryl-4-benzoyl-imidazole (ABI-III) Analogues Targeting Tubulin Polymerization As Antiproliferative Agents

  摘要：

  Novel ABI-III compounds were designed and synthesized based on our previously reported ABI-I and ABI-II analogues. ABI-III compounds are highly potent against a panel of melanoma and prostate cancer cell lines, with the best compound having an average IC50 value of 3.8 nM. They are not substrate of Pgp and thus may effectively overcome Pgp-mediated multidrug resistance. ABI-III analogues maintain their mechanisms of action by inhibition of tubulin polymerization.

  DOI：

  10.1021/jm300564b
• 作为产物：
  描述：

  3-甲醛苯并噻吩 、 草酸醛 在 ammonium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以16.8%的产率得到2-(benzo[b]thiophen-3-yl)-1H-imidazole
  参考文献：
  名称：

  Discovery of Novel 2-Aryl-4-benzoyl-imidazole (ABI-III) Analogues Targeting Tubulin Polymerization As Antiproliferative Agents

  摘要：

  Novel ABI-III compounds were designed and synthesized based on our previously reported ABI-I and ABI-II analogues. ABI-III compounds are highly potent against a panel of melanoma and prostate cancer cell lines, with the best compound having an average IC50 value of 3.8 nM. They are not substrate of Pgp and thus may effectively overcome Pgp-mediated multidrug resistance. ABI-III analogues maintain their mechanisms of action by inhibition of tubulin polymerization.

  DOI：

  10.1021/jm300564b