1-(1H-benzo[d]imidazol-2-yl)-1,2,3,4-tetrahydroquinoline | 929341-92-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(1H-benzo[d]imidazol-2-yl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 1-(1H-benzimidazol-2-yl)-3,4-dihydro-2H-quinoline
• CAS: 929341-92-4
• 化学式: C₁₆H₁₅N₃
• 分子量: 249.315
• InChiKey: VUYWTRRXYXIDQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  31.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以706 mg的产率得到1-(1H-benzo[d]imidazol-2-yl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Rh(III)-Catalyzed [5 + 2] Oxidative Annulation of Cyclic Arylguanidines and Alkynes to 1,3-Benzodiazepines. A Striking Mechanistic Proposal from DFT

  摘要：

  A novel and mild Rh(III)-catalyzed [5 + 2] oxidative annulation between cyclic arylguanidines and alkynes efficiently affords 1,3-benzodiazepines (pentacyclic guanidines). The use of O-2 as the sole oxidant in place of commonly used metal oxidants such as AgOAc clearly improves the efficiency of the oxidative annulation process. The mechanism of the cycloaddition most likely involves the formation of an eight-membered rhodacycle. DFT calculations support a striking mechanistic proposal for the [5 + 2] oxidative annulation.

  DOI：

  10.1021/acs.orglett.9b00354

文献信息

• Identification and optimization of 2-aminobenzimidazole derivatives as novel inhibitors of TRPC4 and TRPC5 channels
  作者：Yingmin Zhu、Yungang Lu、Chunrong Qu、Melissa Miller、Jinbin Tian、Dhananjay P Thakur、Jinmei Zhu、Zixin Deng、Xianming Hu、Meng Wu、Owen B McManus、Min Li、Xuechuan Hong、Michael X Zhu、Huai-Rong Luo

  DOI：10.1111/bph.13140

  日期：2015.7

  high-throughput screening. KEY RESULTS The original compound, M084, was a potent inhibitor of both TRPC4 and TRPC5, but was also a weak inhibitor of TRPC3. Structural modifications of the lead compound resulted in the identification of analogues with improved potency and selectivity for TRPC4 and TRPC5 channels. The aminobenzimidazole derivatives rapidly inhibited the TRPC4- and TRPC5-mediated currents when applied

  背景和目的瞬时受体潜在规范（TRPC）通道在广泛的生理功能中起重要作用，并涉及多种疾病。然而，由于缺乏有效的亚型特异性抑制剂，尚未阐明TRPC通道在生理和病理生理状况中的确切作用。实验方法使用荧光膜电位和Ca（2+）分析和电生理记录，我们表征了新的2-氨基苯并咪唑基的小分子抑制剂TRPC4和TRPC5通道，从基于细胞的荧光高通量筛选中鉴定。关键结果原始化合物M084是TRPC4和TRPC5的有效抑制剂，但也是TRPC3的弱抑制剂。通过对前导化合物进行结构修饰，可以鉴定出对TRPC4和TRPC5通道具有更高效能和选择性的类似物。从细胞外作用时，氨基苯并咪唑衍生物可迅速抑制TRPC4-和TRPC5介导的电流，这种抑制与这些通道的激活方式无关。这些化合物有效地阻断了小鼠外侧中隔神经元中含有TRPC4的通道介导的高原电位，但不影响异源表达的TRPA1，TRPM8，TRPV1或TRPV3通道或天然电压门控Na（+），K的活性。
• Direct, Metal-Free Amination of Heterocyclic Amides/Ureas with NH-Heterocycles and N-Substituted Anilines in POCl₃
  作者：Xiaohu Deng、Armin Roessler、Ivana Brdar、Roger Faessler、Jiejun Wu、Zachary S. Sales、Neelakandha S. Mani

  DOI：10.1021/jo201425q

  日期：2011.10.21

  A POCl3-mediated, direct amination reaction of heterocyclic amides/ureas with NH-heterocycles or N-substituted anilines is described. Compared to the existing methods, this operationally simple protocol provides unique reactivity and functional group compatibility because of the metal-free, acidic reaction conditions. The yields are generally excellent.

  描述了POCl 3介导的杂环酰胺/脲与NH-杂环或N-取代的苯胺的直接胺化反应。与现有方法相比，该操作简单的协议由于无金属的酸性反应条件，提供了独特的反应性和官能团兼容性。产量通常是极好的。
• 一种苯并咪唑类衍生物及其制备方法和应用
  申请人：西藏大学

  公开号：CN108997308A

  公开（公告）日：2018-12-14

  本发明公开了一种苯并咪唑类衍生物及其制备方法和应用，通过本申请制备的苯并咪唑类衍生物能够有效降低吗啡成瘾戒断后的复吸率，对于抑制吗啡戒断症状具有显著的效果，在制备预防和/或治疗成瘾药物成瘾的药物中技术领域中具有广泛的实用性，在制备预防和/或治疗成瘾药物戒断后复吸的药物技术领域中具有较大的开发价值。
• Rh(III)-Catalyzed [5 + 2] Oxidative Annulation of Cyclic Arylguanidines and Alkynes to 1,3-Benzodiazepines. A Striking Mechanistic Proposal from DFT
  作者：Nuria Martínez-Yáñez、Jaime Suárez、Ana Cajaraville、Jesús A. Varela、Carlos Saá

  DOI：10.1021/acs.orglett.9b00354

  日期：2019.3.15

  A novel and mild Rh(III)-catalyzed [5 + 2] oxidative annulation between cyclic arylguanidines and alkynes efficiently affords 1,3-benzodiazepines (pentacyclic guanidines). The use of O-2 as the sole oxidant in place of commonly used metal oxidants such as AgOAc clearly improves the efficiency of the oxidative annulation process. The mechanism of the cycloaddition most likely involves the formation of an eight-membered rhodacycle. DFT calculations support a striking mechanistic proposal for the [5 + 2] oxidative annulation.