1-benzyl-N-phenyl-1H-benzo[d]imidazol-2-amine | 24068-33-5

• 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: 1-benzyl-N-phenyl-1H-benzo[d]imidazol-2-amine
• 英文别名: 1-benzyl-2-phenylaminobenzimidazole；(1-benzyl-1H-benzoimidazol-2-yl)-phenyl-amine；2-Anilino-1-benzyl-benzimidazol；2-Anilino-1-benzylbenzimidazol；1-benzyl-N-phenylbenzimidazol-2-amine
• CAS: 24068-33-5
• 化学式: C₂₀H₁₇N₃
• mdl: MFCD02983731
• 分子量: 299.375
• InChiKey: QQZALSKVCZVWBY-UHFFFAOYSA-N

物化性质

• 熔点：
  238 °C(Solv: ethanol (64-17-5))
• 沸点：
  505.2±43.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯苯并咪唑 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 13.5h， 生成 1-benzyl-N-phenyl-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903

  摘要：

  The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biological characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of AC1903, a TRPC5 inhibitor that is active in multiple animal models of CKD.

  DOI：

  10.1016/j.bmcl.2018.12.007

文献信息

• NaI-Mediated Electrochemical Cyclization–Desulfurization for the Synthesis of <i>N</i>-Substituted 2-Aminobenzimidazoles
  作者：Khuyen Thu Nguyen、Thao Nguyen Thanh Huynh、Kanisorn Ratanathawornkiti、Methasit Juthathan、Patchanita Thamyongkit、Mongkol Sukwattanasinitt、Sumrit Wacharasindhu

  DOI：10.1021/acs.joc.3c02212

  日期：2024.2.2

  An electrochemical method for the synthesis of N-substituted 2-aminobenzimidazoles through a NaI-mediated desulfurization–cyclization process is reported. This electrosynthesis method utilizes cost-effective NaI as both a mediator and an electrolyte in a catalytic amount (0.2 equiv), replacing traditional oxidizing reagents. N-Substituted o-phenylenediamines and isothiocyanates undergo a thiourea

  报道了一种通过 NaI 介导的脱硫环化过程合成N-取代 2-氨基苯并咪唑的电化学方法。这种电合成方法利用经济高效的 NaI 作为介体和催化量（0.2 当量）的电解质，取代了传统的氧化剂。 N-取代的邻苯二胺和异硫氰酸酯经过硫脲形成/环化/脱硫过程，在单个反应容器中提供N-取代的2-氨基苯并咪唑（55个实例，产率高达98%）。重要的是，这种电化学方法适用于克级合成，保持反应效率。
• Microwave-assisted hydrogen peroxide-mediated synthesis of benzoxazoles and related heterocycles <i>via</i> cyclodesulfurization
  作者：Manasa Kadagathur、Dilep Kumar Sigalapalli、Sandip Patra、Neelima D. Tangellamudi

  DOI：10.1080/00397911.2021.1928217

  日期：2021.7.18
• Condensed derivatives of benzazoles. 1. Synthesis of 6- and 5-substituted benzimidazo[2,1-b]quinazolin-12-ones
  作者：I. I. Popov、S. L. Boroshko、B. A. Tertov、S. P. Makarov、A. M. Simonov、B. Ya. Simkin

  DOI：10.1007/bf00472263

  日期：1987.12
• POPOV, I. I.;BOROSHKO, S. L.;TERTOV, B. A.;MAKAROV, S. P.;SIMONOV, A. M.;+, XIMIYA GETEROTSIKL. SOED.,(1987) N 12, 1673-1677
  作者：POPOV, I. I.、BOROSHKO, S. L.、TERTOV, B. A.、MAKAROV, S. P.、SIMONOV, A. M.、+

  DOI：——

  日期：——
• Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903
  作者：Swagat H. Sharma、Juan Lorenzo Pablo、Monica Suarez Montesinos、Anna Greka、Corey R. Hopkins

  DOI：10.1016/j.bmcl.2018.12.007

  日期：2019.1

  The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biological characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of AC1903, a TRPC5 inhibitor that is active in multiple animal models of CKD.