2-(4-乙基苯基)-1H-咪唑 | 164062-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-乙基苯基)-1H-咪唑
• 英文名称: (4-ethylphenyl)-1H-imidazol
• 英文别名: 2-(4-Ethylphenyl)-1H-imidazole
• CAS: 164062-69-5
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: MEYVERJDFPIURX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-乙基苯基)-1H-咪唑 在 四丁基氟化铵 、 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 、 正戊烷 为溶剂， 生成 [2-(4-Ethylphenyl)-1H-imidazol-5-yl](3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Discovery of 4-Aryl-2-benzoyl-imidazoles as Tubulin Polymerization Inhibitor with Potent Antiproliferative Properties

  摘要：

  A series of 4-aryl-2-benzoyl-imidazoles were designed and synthesized based on our previously reported 2-aryl-4-benzoyl-imidazole (ABI) derivatives. The new structures reversed the aryl group and the benzoyl group of previous ABI structures and were named as reverse ABI (RABI) analogues. RABIs were evaluated for biological activity against eight cancer cell lines including multidrug-resistant cancer cell lines. In vitro assays indicated that several RABI compounds had excellent antiproliferative properties, with IC50 values in the low, nanomolar range. The average IC50 of the most active compound 12a is 14 nM. In addition, the mechanism of action of these new analogues was investigated by cell cycle analysis, tubulin polymerization assay, competitive mass spectrometry binding assay, and molecular docking studies. These studies confirmed that these new RABI analogues maintain their mechanisms of action by disrupting tubulin polymerization, similar to their parental ABI analogues.

  DOI：

  10.1021/jm4001117
• 作为产物：
  描述：

  草酸醛 、 4-乙基苯甲醛 在 ammonium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 生成 2-(4-乙基苯基)-1H-咪唑
  参考文献：
  名称：

  Discovery of 4-Aryl-2-benzoyl-imidazoles as Tubulin Polymerization Inhibitor with Potent Antiproliferative Properties

  摘要：

  A series of 4-aryl-2-benzoyl-imidazoles were designed and synthesized based on our previously reported 2-aryl-4-benzoyl-imidazole (ABI) derivatives. The new structures reversed the aryl group and the benzoyl group of previous ABI structures and were named as reverse ABI (RABI) analogues. RABIs were evaluated for biological activity against eight cancer cell lines including multidrug-resistant cancer cell lines. In vitro assays indicated that several RABI compounds had excellent antiproliferative properties, with IC50 values in the low, nanomolar range. The average IC50 of the most active compound 12a is 14 nM. In addition, the mechanism of action of these new analogues was investigated by cell cycle analysis, tubulin polymerization assay, competitive mass spectrometry binding assay, and molecular docking studies. These studies confirmed that these new RABI analogues maintain their mechanisms of action by disrupting tubulin polymerization, similar to their parental ABI analogues.

  DOI：

  10.1021/jm4001117

文献信息

• [EN] THERAPEUTIC BISPHOSPHONATES<br/>[FR] BISPHOSPHONATES THÉRAPEUTIQUES
  申请人：UNIV IOWA RES FOUND

  公开号：WO2014008407A1

  公开（公告）日：2014-01-09

  The invention provides novel pyrophosphate synthase inhibitors of formula I and formula II as well salts thereof; the invention also provides compositions comprising such inhibitors and methods for their use.

  本发明提供了新颖的焦磷酸合成酶抑制剂，其化学式为I和II以及它们的盐；本发明还提供了包含这些抑制剂的组合物及其使用方法。
• Ganguly, Swastika; Shaw, Priya, Indian Journal of Heterocyclic Chemistry, 2019, vol. 29, # 1, p. 5 - 10
  作者：Ganguly, Swastika、Shaw, Priya

  DOI：——

  日期：——
• THERAPEUTIC BISPHOSPHONATES
  申请人：University of Iowa Research Foundation

  公开号：EP2870168B1

  公开（公告）日：2016-11-23
• METHODS TO MODULATE RAC1 IMPORT AND TO TREAT PULMONARY FIBROSIS
  申请人：University of Iowa Research Foundation

  公开号：US20150005261A1

  公开（公告）日：2015-01-01

  The invention provides methods for treating fibrosis, as well as methods for modulating mitochondrial peroxide production in a cell, and methods for modulating the import of Rac1 into the mitochondria of a cell.
• US9416149B2
  申请人：——

  公开号：US9416149B2

  公开（公告）日：2016-08-16