N-(1H-benzo[d]imidazole-2-yl)-4-methylbenzamide | 55842-44-9

• 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-(1H-benzo[d]imidazole-2-yl)-4-methylbenzamide
• 英文别名: 2-(4-Methylphenylcarbonylamino)-benzimidazol；N-(1H-benzo[d]imidazol-2-yl)-4-methylbenzamide；N-(1H-benzoimidazol-2-yl)-4-methyl-benzamide；N-(1,3-dihydrobenzimidazol-2-ylidene)-4-methylbenzamide
• CAS: 55842-44-9
• 化学式: C₁₅H₁₃N₃O
• mdl: MFCD01339467
• 分子量: 251.288
• InChiKey: MCPFWFXITVMKRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1H-benzo[d]imidazole-2-yl)-4-methylbenzamide 在 sodium azide 、 五氯化磷 作用下， 生成 2-(5-p-Tolyl-tetrazol-1-yl)-1H-benzoimidazole
  参考文献：
  名称：

  Rao, P. Jayaprasad; Reddy, K. Kondal, Synthetic Communications, 1988, vol. 18, # 16-17, p. 1995 - 2002

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(4'-methylphenyl)carbonyl-3-(2'-aminophenyl)thiourea 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以95%的产率得到N-(1H-benzo[d]imidazole-2-yl)-4-methylbenzamide
  参考文献：
  名称：

  磷介导的N-（2-氨基苯基）硫脲的环化：2-氨基苯并咪唑的有效合成

  摘要：

  BOP有效地促进了promote介导的硫脲的环化，从而导致了2-氨基苯并咪唑的方便合成。与常规方法相比，反应在室温下以几分钟到1小时的时间完成，收率接近定量。该方法也可用于合成更具挑战性的结构，例如2-烷基氨基苯并咪唑和2-（N-酰基）-氨基苯并咪唑。本文所述的方法学是制备各种2-氨基苯并咪唑的温和而有效的途径。

  DOI：

  10.1016/j.tetlet.2011.05.146

文献信息

• Optimisation of in silico derived 2-aminobenzimidazole hits as unprecedented selective kappa opioid receptor agonists
  作者：Pradip K. Sasmal、C. Vamsee Krishna、S. Sudheerkumar Adabala、M. Roshaiah、Khaji Abdul Rawoof、Emima Thadi、K. Pavan Sukumar、Srisailam Cheera、Chandrasekhar Abbineni、K.V.L. Narasimha Rao、A. Prasanthi、Kamal Nijhawan、Mahaboobi Jaleel、Lakshmi Ramachandran Iyer、T. Krishna Chaitanya、Nirbhay Kumar Tiwari、N. Lavanya Krishna、Vijay Potluri、Ish Khanna、Thomas M. Frimurer、Michael Lückmann、Øystein Rist、Lisbeth Elster、Thomas Högberg

  DOI：10.1016/j.bmcl.2014.12.064

  日期：2015.2

  Kappa opioid receptor (KOR) is an important mediator of pain signaling and it is targeted for the treatment of various pains. Pharmacophore based mining of databases led to the identification of 2-aminobenzimidazole derivative as KOR agonists with selectivity over the other opioid receptors DOR and MOR. A short SAR exploration with the objective of identifying more polar and hence less brain penetrant agonists is described herewith. Modeling studies of the recently published structures of KOR, DOR and MOR are used to explain the receptor selectivity. The synthesis, biological evaluation and SAR of novel benzimidazole derivatives as KOR agonists are described. The in vivo proof of principle for anti-nociceptive effect with a lead compound from this series is exemplified. (C) 2014 Elsevier Ltd. All rights reserved.
• PTSA catalyzed straightforward protocol for the synthesis of 2-(N-acyl)aminobenzimidazoles and 2-(N-acyl)aminobenzothiazoles in PEG
  作者：Siddaiah Vidavalur、Mahaboob Basha Gajula、Ramu Tadikonda、Mangarao Nakka、Sudhakar Dega、Santosh Kumar Yadav、Christopher Voosala

  DOI：10.1016/j.tetlet.2014.03.040

  日期：2014.4

  An efficient PTSA catalyzed synthesis of 2-(N-acyl)aminobenzimidazoles and 2-(N-acyl)aminobenzothiazoles has been described using S-ethylated-N-acylthioureas as substrates and polyethylene glycol as solvent. (C) 2014 Elsevier Ltd. All rights reserved.
• Sridevi, G.; Rao, P. Jayaprasad; Reddy, K. Kondal, Synthetic Communications, 1989, vol. 19, # 5and6, p. 965 - 972
  作者：Sridevi, G.、Rao, P. Jayaprasad、Reddy, K. Kondal

  DOI：——

  日期：——
• RAO, P. JAYAPRASAD;REDDY, K. KONDAL, SYNTH. COMMUN., 18,(1988) N 16-17, C. 1995-2001
  作者：RAO, P. JAYAPRASAD、REDDY, K. KONDAL

  DOI：——

  日期：——
• PI3-KINASEN INHIBITOREN
  申请人：BOEHRINGER INGELHEIM INTERNATIONAL GMBH

  公开号：EP1802636B1

  公开（公告）日：2013-03-27