2-chloro-1-(4-isopropylbenzyl)benzimidazole

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-chloro-1-(4-isopropylbenzyl)benzimidazole
• 英文别名: 2-chloro-1-(4-isopropylbenzyl)-1H-benzo[d]imidazole；2-chloro-1-[(4-propan-2-ylphenyl)methyl]benzimidazole
• 化学式: C₁₇H₁₇ClN₂
• 分子量: 284.788
• InChiKey: QZMSDTGDWCYGLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-1-(4-isopropylbenzyl)benzimidazole 在 三乙胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 10.5h， 生成 9-(4-isopropylbenzyl)-2,9-dihydro-3H-benzo[d]imidazo[1,2-a]imidazole
  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：

  对异丙基溴苄 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三氯氧磷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 2-chloro-1-(4-isopropylbenzyl)benzimidazole
  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

• PYRIDINE AND PYRIMIDINE DERIVATIVES AS PHOSPHODIESTERASE 10 INHIBITORS
  申请人：Allen Jennifer R.

  公开号：US20100125062A1

  公开（公告）日：2010-05-20

  Pyridine and pyrimidine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

  吡啶和嘧啶化合物，以及含有它们的组合物，以及制备这些化合物的方法。本文还提供了治疗通过抑制PDE10可治疗的疾病或疾病的方法，如肥胖症、非胰岛素依赖型糖尿病、精神分裂症、躁郁症、强迫症等。
• Synthesis and Cytotoxic Evaluation of Pyrrole Hetarylazoles Containing Benzimidazole/Pyrazolone/1,3,4-Oxadiazole Motifs
  作者：Bereket Mochona、Timothy Jackson、DeCoria McCauley、Elizabeth Mazzio、Kinfe K. Redda

  DOI：10.1002/jhet.2501

  日期：2016.11

  Azomethine linked pyrrole bishetarylazoles containing benzimidazole/pyrazolone/1,3,4-oxadiazole were synthesized in satisfactory yields. Their structures were confirmed by IR, 1H-NMR, 13C-NMR and elemental analysis. Evaluation for the cytotoxic activities In vitro against a panel of breast cancer cell lines (MDA-AB-231, BT-474 and Ishikawa cells) revealed that the pyrrole-benzimidazole hybrids are

  合成了含有苯并咪唑/吡唑酮/1,3,4-恶二唑的偶氮甲碱连接的吡咯二杂芳唑，收率令人满意。其结构经IR、1H-NMR、13C-NMR和元素分析证实。对一组乳腺癌细胞系（MDA-AB-231、BT-474 和 Ishikawa 细胞）的体外细胞毒活性评估表明，吡咯-苯并咪唑杂合体比吡唑啉酮和 1,3,4-恶二唑更有效所有细胞系中的杂种。化合物 (9) 对 BT-474 细胞系表现出良好的细胞毒性，IC50 值为 7.7 µM。
• Pyridine and pyrimidine derivatives as phosphodiesterase 10 inhibitors
  申请人：Amgen Inc.

  公开号：EP2364306B1

  公开（公告）日：2013-04-24
• US8318718B2
  申请人：——

  公开号：US8318718B2

  公开（公告）日：2012-11-27
• [EN] PYRIDINE AND PYRIMIDINE DERIVATIVES AS PHOSPHODIESTERASE 10 INHIBITORS<br/>[FR] DERIVES DE PYRIDINE ET DE PYRIMIDINE COMME INHIBITEURS DE PHOSPHODIESTERASE 10
  申请人：AMGEN INC

  公开号：WO2010057126A1

  公开（公告）日：2010-05-20

  Pyridine and pyrimidine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.