1-(4-叔-丁基苄基)-1H-苯并[d]咪唑-2(3H)-酮 | 537702-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-(4-叔-丁基苄基)-1H-苯并[d]咪唑-2(3H)-酮
• 英文名称: 1-(4-tert-butylbenzyl)-1,3-dihydro-benzimidazol-2-one
• 英文别名: 1-(4-Tert-butylbenzyl)-1,3-dihydrobenzimidazol-2-one；3-[(4-tert-butylphenyl)methyl]-1H-benzimidazol-2-one
• CAS: 537702-33-3
• 化学式: C₁₈H₂₀N₂O
• mdl: MFCD03672945
• 分子量: 280.37
• InChiKey: LGKHIOBIOKZZEY-UHFFFAOYSA-N

物化性质

• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-叔-丁基苄基)-1H-苯并[d]咪唑-2(3H)-酮 在 盐酸 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-dihydroimidazo[1,2-a]benzimidazole derivatives against Leishmania donovani and Trypanosoma cruzi

  摘要：

  A high-throughput (HTS) and high-content screening (HCS) campaign of a commercial library identified 2,3-dihydroimidazo[1,2-a]benzimidazole analogues as a novel class of anti-parasitic agents. A series of synthetic derivatives were evaluated for their in vitro anti-leishmanial and anti-trypanosomal activities against Leishmania donovani and Trypanosoma cruzi, which have been known as the causative parasites for visceral leishmaniasis and Chagas disease, respectively. In the case of Leishmania, the compounds were tested in both intracellular amastigote and extracellular promastigote assays. Compounds 4 and 24 showed promising anti-leishmanial activity against intracellular L. donovani (3.05 and 5.29 μM, respectively) and anti-trypanosomal activity against T. cruzi (1.10 and 2.10 μM, respectively) without serious cytotoxicity toward THP-1 and U2OS cell lines.

  DOI：

  10.1016/j.ejmech.2014.07.038
• 作为产物：
  描述：

  2-硝基苯胺 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 1-(4-叔-丁基苄基)-1H-苯并[d]咪唑-2(3H)-酮
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-dihydroimidazo[1,2-a]benzimidazole derivatives against Leishmania donovani and Trypanosoma cruzi

  摘要：

  A high-throughput (HTS) and high-content screening (HCS) campaign of a commercial library identified 2,3-dihydroimidazo[1,2-a]benzimidazole analogues as a novel class of anti-parasitic agents. A series of synthetic derivatives were evaluated for their in vitro anti-leishmanial and anti-trypanosomal activities against Leishmania donovani and Trypanosoma cruzi, which have been known as the causative parasites for visceral leishmaniasis and Chagas disease, respectively. In the case of Leishmania, the compounds were tested in both intracellular amastigote and extracellular promastigote assays. Compounds 4 and 24 showed promising anti-leishmanial activity against intracellular L. donovani (3.05 and 5.29 μM, respectively) and anti-trypanosomal activity against T. cruzi (1.10 and 2.10 μM, respectively) without serious cytotoxicity toward THP-1 and U2OS cell lines.

  DOI：

  10.1016/j.ejmech.2014.07.038

文献信息

• Substituted Cyclic Urea Derivatives and the Use Thereof as Vanilloid Receptor 1 Modulators
  申请人：FRANK Robert

  公开号：US20080090855A1

  公开（公告）日：2008-04-17

  The present invention relates to substituted cyclic urea derivatives corresponding to formula I, to processes for the preparation thereof, to medicinal drugs containing such compounds, to the use of such compounds in the preparation of medicinal drugs and in related treatment methods.

  本发明涉及对应于式I的取代环状脲衍生物，其制备方法，含有此类化合物的药物，以及在相关治疗方法中使用此类化合物制备药物的用途。
• Substituted cyclic urea derivatives and the use thereof as vanilloid receptor 1 modulators
  申请人：Gruenenthal GmbH

  公开号：US08207182B2

  公开（公告）日：2012-06-26

  The present invention relates to substituted cyclic urea derivatives corresponding to formula I, to processes for the preparation thereof, to medicinal drugs containing such compounds, to the use of such compounds in the preparation of medicinal drugs and in related treatment methods.

  本发明涉及与式I相对应的取代环状脲衍生物，其制备方法，含有这种化合物的药物，以及在制备药物和相关治疗方法中使用这种化合物的用途。
• Design, synthesis, <i>in silico</i>, and <i>in vitro</i> evaluation of benzylbenzimidazolone derivatives as potential drugs on α-glucosidase and glucokinase as pharmacological targets
  作者：Cress Lumadhar Santos-Ballardo、Julio Montes-Ávila、José Guadalupe Rendon-Maldonado、Rosalio Ramos-Payan、Sarita Montaño、Juan I. Sarmiento-Sánchez、Selene de Jesús Acosta-Cota、Adrián Ochoa-Terán、Pedro de Jesús Bastidas-Bastidas、Ulises Osuna-Martínez

  DOI：10.1039/d3ra02916f

  日期：——

  delimitate the selection of structures to synthesize and the in vitro evaluation of benzimidazolone derivatives in blood glucose control. A docking of 23 benzimidazolone derivatives was performed; selecting the compounds with better in silico profiles to synthesize by microwave-irradiation/conventional heat and evaluate in enzymatic in vitro evaluation. Compounds 2k, 2m, 2r, and 2s presented the best in silico

  苯并咪唑酮已显示出生物活性，包括通过抑制或激活 α-glu 和 GK 来降血糖和降血糖。本研究的目的是使用计算机分析合理设计化合物，以界定合成结构的选择以及苯并咪唑酮衍生物在血糖控制中的体外评价。进行了23种苯并咪唑酮衍生物的对接；选择具有更好计算机特征的化合物通过微波辐射/常规加热进行合成并在体外酶促评价中进行评价。化合物2k 、 2m 、 2r和2s在计算机模拟中表现出最好的特征，显示出良好的亲和能（-10.9 至 -8.6 kcal mol -1 ）并与催化氨基酸结合。它们使用 DMF 作为溶剂和碳酸钾在 70°C 24 小时下合成（产率：22-38%）。 α-glu 的结果显示对2k (14 ± 1.23–29 ± 0.45)、 2m (12 ± 2.21–36 ± 0.30)、 2r (7 ± 2.21–13 ± 1.34) 和2s (11 ± 0.74– 35 ± 2.95）在评估浓度（0
• Discovery of novel, orally available benzimidazoles as melanin concentrating hormone receptor 1 (MCHR1) antagonists
  作者：Pradip K. Sasmal、Sanjita Sasmal、P. Tirumala Rao、B. Venkatesham、M. Roshaiah、Chandrasekhar Abbineni、Ish Khanna、Vikram P. Jadhav、J. Suresh、Rashmi Talwar、Syed Muzeeb、Jean-Marie Receveur、Thomas M. Frimurer、Øystein Rist、Lisbeth Elster、Thomas Högberg

  DOI：10.1016/j.bmcl.2010.07.086

  日期：2010.9

  Melanin concentrating hormone (MCH) is an important mediator of energy homeostasis and plays role in several disorders such as obesity, stress, depression and anxiety. The synthesis and biological evaluation of novel benzimidazole derivatives as MCHR1 antagonists are described. The in vivo proof of principle for weight loss with a lead compound from this series is exemplified. (c) 2010 Elsevier Ltd. All rights reserved.
• WO2006/111346
  申请人：——

  公开号：——

  公开（公告）日：——