N-phenyl-2-(2-quinolyl)benzimidazole | 1245810-86-9

• 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: N-phenyl-2-(2-quinolyl)benzimidazole
• 英文别名: 2-(1-phenyl-1H-benzo[d]imidazol-2-yl)quinoline；2-(1-Phenylbenzimidazol-2-yl)quinoline；2-(1-phenylbenzimidazol-2-yl)quinoline
• CAS: 1245810-86-9
• 化学式: C₂₂H₁₅N₃
• 分子量: 321.381
• InChiKey: DHXALBGMCVLUQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基喹啉 在 碘 、 二甲基亚砜 作用下， 反应 8.0h， 生成 N-phenyl-2-(2-quinolyl)benzimidazole
  参考文献：
  名称：

  Iodine-catalyzed Csp3-H functionalization of methylhetarenes: One-pot synthesis and cytotoxic evaluation of heteroarenyl-benzimidazoles and benzothiazole

  摘要：

  An efficient one-pot synthetic procedure has been developed for the preparation of heteroarenyl-benzim-dazoles via oxidative C-sp3-H functionalization with o-phenylenediamine using I-2-DMSO in open air from easily available starting materials. Based on a logical plan a spectrum of multi fundamental reactions like iodination, Kornblum oxidation and amination were brought into one-pot. By using this simple method a library of heteroarenyl-benzimidazoles derivatives (3a-t and 5a-g) and heteroarenyl-benzothiazole (3u) have been synthesized in good to excellent yield and screened for their cytotoxicity against a group of four human cancer cell lines. Among them 3h, 3q and 5b showed significant cytotoxic activities with an IC50 of 1.69, 1.62 and 2.81 mu M respectively against lung cancer (A549) cell line. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.07.051

文献信息

• Organocatalytic functionalization of heteroaromatic N-oxides with C-nucleophiles using in situ generated onium amide bases
  作者：Kiyofumi Inamoto、Yuta Araki、Shoko Kikkawa、Misato Yonemoto、Yoshiyuki Tanaka、Yoshinori Kondo

  DOI：10.1039/c3ob40782a

  日期：——

  Organocatalytic functionalization of heteroaromatic N-oxides was investigated using in situ generated onium amide bases, and C-nucleophiles were efficiently introduced by the sequential addition–elimination reaction under metal-free conditions, affording 2-substituted nitrogen heteroaromatics generally in good to high yields.

  有机催化功能化杂芳香N-氧化物研究采用了原位生成鎓酰胺碱基的方法，在无金属条件下通过连续加成-消除反应，高效引入了C亲核试剂，一般以良好至高产率得到了2-取代的氮杂芳香化合物。
• Iodine-catalyzed Csp3-H functionalization of methylhetarenes: One-pot synthesis and cytotoxic evaluation of heteroarenyl-benzimidazoles and benzothiazole
  作者：Mirza Feroz Baig、Siddiq Pasha Shaik、V. Lakshma Nayak、Abdullah Alarifi、Ahmed Kamal

  DOI：10.1016/j.bmcl.2017.07.051

  日期：2017.9

  An efficient one-pot synthetic procedure has been developed for the preparation of heteroarenyl-benzim-dazoles via oxidative C-sp3-H functionalization with o-phenylenediamine using I-2-DMSO in open air from easily available starting materials. Based on a logical plan a spectrum of multi fundamental reactions like iodination, Kornblum oxidation and amination were brought into one-pot. By using this simple method a library of heteroarenyl-benzimidazoles derivatives (3a-t and 5a-g) and heteroarenyl-benzothiazole (3u) have been synthesized in good to excellent yield and screened for their cytotoxicity against a group of four human cancer cell lines. Among them 3h, 3q and 5b showed significant cytotoxic activities with an IC50 of 1.69, 1.62 and 2.81 mu M respectively against lung cancer (A549) cell line. (C) 2017 Elsevier Ltd. All rights reserved.