6-Chloro-1-methylbenzimidazol-2-amine | 925460-91-9

• 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: 6-Chloro-1-methylbenzimidazol-2-amine
• CAS: 925460-91-9
• 化学式: C₈H₈ClN₃
• 分子量: 181.625
• InChiKey: NSJJFVCJPRXNRE-UHFFFAOYSA-N

物化性质

• 沸点：
  370.1±34.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-氯-2-甲氧基苯甲醛 、 6-Chloro-1-methylbenzimidazol-2-amine 在 sodium tetrahydroborate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  In vitro activity of new N-benzyl-1H-benzimidazol-2-amine derivatives against cutaneous, mucocutaneous and visceral Leishmania species

  摘要：

  The identification of specific therapeutic targets and the development of new drugs against leishmaniasis are urgently needed, since chemotherapy currently available for its treatment has several problems including many adverse side effects. In an effort to develop new antileishmanial drugs, in the present study a series of 28 N-benzyl-1H-benzimidazol-2-amine derivatives was synthesized and evaluated in vitro against Leishmania mexicana promastigotes. Compounds 7 and 8 with the highest antileishmanial activity (micromolar) and lower cytotoxicity than miltefosine and amphotericin B were selected to evaluate their activity against L braziliensis 9 and L donovani, species causative of mucocutaneous and visceral leishmaniasis, respectively. Compound 7 showed significantly higher activity against L. braziliensis promastigotes than compound 8 and slightly lower than miltefosine. Compounds 7 and 8 had 1050 values in the micromolar range against the amastigote of L mexicana and L braziliensis. However, both compounds did not show better activity against L donovani than miltefosine. Compound 8 showed the highest SI against both parasite stages of L mexicana. In addition, compound 8 inhibited 68.27% the activity of recombinant L mexicana arginase (LmARG), a therapeutic target for the treatment of leishmaniasis. Docking studies were also performed in order to establish the possible mechanism of action by which this compound exerts its inhibitory effect. Compound 8 shows promising potential for the development of more potent antileishmanial benzimidazole derivatives. (C) 2017 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.exppara.2017.11.009
• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 6-Chloro-1-methylbenzimidazol-2-amine
  参考文献：
  名称：

  Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action

  摘要：

  In this report we describe 2-iminobenzimidazole (IBI) analogs, identified during the course of a phenotypic high-throughput screening campaign, as novel hepatitis C virus (HCV) inhibitors. A series of IBI derivatives was synthesized and evaluated for their inhibitory activity against infectious HCV. Among the IBIs derivatives studied in this work, we identified promising compounds with high antiviral efficacy, high selectivity index and good microsomal stability. Noteworthy, the IBI series exhibited inhibitory activity on early and late steps of the viral cycle, but not in the HCV replicon system demonstrating a mechanism of action distinct from clinical-stage and approved anti-HCV drugs. Overall, our results suggest that IBIs are predestinated for further exploration as lead compounds for novel HCV interventions. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.030

文献信息

• [EN] HETEROCYCLIC COMPOUNDS CONTAINING AN INDOLE CORE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES CONTENANT UN COEUR INDOLE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011071716A1

  公开（公告）日：2011-06-16

  Disclosed are novel compounds which inhibit RSK, methods of making such compounds and pharmaceutical compositions comprising such compounds. Also disclosed are methods of treating RSK2 regulated disorders using compounds of the invention.

  公开了抑制RSK的新颖化合物，制造此类化合物的方法以及包含此类化合物的药物组合物。还公开了使用本发明的化合物治疗RSK2调控失调的方法。
• HETEROCYCLIC COMPOUNDS CONTAINING AN INDOLE CORE
  申请人：Boyer Stephen James

  公开号：US20130109679A1

  公开（公告）日：2013-05-02

  Disclosed are novel compounds which inhibit RSK, methods of making such compounds and pharmaceutical compositions comprising such compounds. Also disclosed are methods of treating RSK2 regulated disorders using compounds of the invention.

  本发明揭示了一种新型化合物，可抑制RSK，制备这种化合物的方法以及包含这种化合物的药物组合物。本发明还揭示了使用本发明化合物治疗RSK2调节的疾病的方法。
• US9150577B2
  申请人：——

  公开号：US9150577B2

  公开（公告）日：2015-10-06