(2-(4-(benzyloxy)phenyl)-1H-benzoimidazol-5-yl)(phenyl)methanone | 1426227-69-1

• 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: (2-(4-(benzyloxy)phenyl)-1H-benzoimidazol-5-yl)(phenyl)methanone
• 英文别名: phenyl-[2-(4-phenylmethoxyphenyl)-3H-benzimidazol-5-yl]methanone
• CAS: 1426227-69-1
• 化学式: C₂₇H₂₀N₂O₂
• 分子量: 404.468
• InChiKey: MFDQGOLZBOHNAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-(4-(benzyloxy)phenyl)-1H-benzoimidazol-5-yl)(phenyl)methanone 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 1.0h， 以57%的产率得到[2-(4-benzyloxy-phenyl)-1H-benzoimidazol-5-yl]phenylmethanol
  参考文献：
  名称：

  2-苯基苯并咪唑作为潜在抗癌药物的合成及其构效关系的研究

  摘要：

  为了探索和开发新型抗癌药物，利用焦亚硫酸钠作为氧化剂，在简单温和的条件下缩合了三个系列的2-苯基苯并咪唑15-46 ，并通过使用还原剂进行还原反应得到了另一个系列47-55 。硼氢化钠。评估了所有合成的化合物对三种人类癌细胞系的体外抗癌活性。新型化合物38被发现是针对A549、MDA-MB-231和PC3细胞系最有效的多癌症抑制剂（IC 50值分别为4.47、4.68和5.50 μg mL -1 ）。此外，化合物40对MDA-MB-231细胞系表现出最佳IC 50值，为3.55 μg mL -1 。结果表明，向化合物37-55引入新的取代基可以提高其抗增殖活性。

  DOI：

  10.1039/d0ra02282a
• 作为产物：
  描述：

  2-(4-Phenylmethoxyphenyl)-1,3-dioxane 在 sodium metabisulfite 、 水 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 (2-(4-(benzyloxy)phenyl)-1H-benzoimidazol-5-yl)(phenyl)methanone
  参考文献：
  名称：

  Benzimidazole-carboxamides as potent and bioavailable stearoyl-CoA desaturase (SCD1) inhibitors from ligand-based virtual screening and chemical optimization

  摘要：

  The discovery of potent benzimidazole stearoyl-CoA desaturase (SCD1) inhibitors by ligand-based virtual screening is described. ROCS 3D-searching gave a favorable chemical motif that was subsequently optimized to arrive at a chemical series of potent and promising SCD1 inhibitors. In particular, compound SAR224 was selected for further pharmacological profiling based on favorable in vitro data. After oral administration to male ZDF rats, this compound significantly decreased the serum fatty acid desaturation index, thus providing conclusive evidence for SCD1 inhibition in vivo by SAR224. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.030

文献信息

• Synthesis and insight into the structure–activity relationships of 2-phenylbenzimidazoles as prospective anticancer agents
  作者：Thi-Kim-Chi Huynh、Thi-Hong-An Nguyen、Thi-Cam-Thu Nguyen、Thi-Kim-Dung Hoang

  DOI：10.1039/d0ra02282a

  日期：——

  In order to explore and develop new anticancer agents, three series of 2-phenylbenzimidazoles, 15–46, were condensed under simple and mild conditions using sodium metabisulfite as an oxidation agent and another series, 47–55, were obtained via a reduction reaction using sodium borohydride. All the compounds synthesized were evaluated for their in vitro anticancer activities against three human cancer

  为了探索和开发新型抗癌药物，利用焦亚硫酸钠作为氧化剂，在简单温和的条件下缩合了三个系列的2-苯基苯并咪唑15-46 ，并通过使用还原剂进行还原反应得到了另一个系列47-55 。硼氢化钠。评估了所有合成的化合物对三种人类癌细胞系的体外抗癌活性。新型化合物38被发现是针对A549、MDA-MB-231和PC3细胞系最有效的多癌症抑制剂（IC 50值分别为4.47、4.68和5.50 μg mL -1 ）。此外，化合物40对MDA-MB-231细胞系表现出最佳IC 50值，为3.55 μg mL -1 。结果表明，向化合物37-55引入新的取代基可以提高其抗增殖活性。
• Benzimidazole-carboxamides as potent and bioavailable stearoyl-CoA desaturase (SCD1) inhibitors from ligand-based virtual screening and chemical optimization
  作者：Hans Matter、Gerhard Zoller、Andreas W. Herling、Juan-Antonio Sanchez-Arias、Christophe Philippo、Claudie Namane、Markus Kohlmann、Anja Pfenninger、Marc D. Voss

  DOI：10.1016/j.bmcl.2013.01.030

  日期：2013.3

  The discovery of potent benzimidazole stearoyl-CoA desaturase (SCD1) inhibitors by ligand-based virtual screening is described. ROCS 3D-searching gave a favorable chemical motif that was subsequently optimized to arrive at a chemical series of potent and promising SCD1 inhibitors. In particular, compound SAR224 was selected for further pharmacological profiling based on favorable in vitro data. After oral administration to male ZDF rats, this compound significantly decreased the serum fatty acid desaturation index, thus providing conclusive evidence for SCD1 inhibition in vivo by SAR224. (C) 2013 Elsevier Ltd. All rights reserved.