4,6-dimethyl-1H-benzo[d]imidazole-2-carboxylic acid | 1432645-43-6

• 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: 4,6-dimethyl-1H-benzo[d]imidazole-2-carboxylic acid
• 英文别名: 4,6-Dimethylbenzimidazole-2-carboxylic Acid；4,6-dimethyl-1H-benzimidazole-2-carboxylic acid
• CAS: 1432645-43-6
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: HJQJNYPECRVVLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基金刚烷 、 4,6-dimethyl-1H-benzo[d]imidazole-2-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以44%的产率得到N-(2-adamantyl)-4,6-dimethyl-1H-benzo[d]imidazole-2-carboxamide
  参考文献：
  名称：

  Preliminary Structure–Activity Relationships and Biological Evaluation of Novel Antitubercular Indolecarboxamide Derivatives Against Drug-Susceptible and Drug-Resistant Mycobacterium tuberculosis Strains

  摘要：

  Tuberculosis (TB) remains one of the leading causes of mortality and morbidity worldwide, with approximately one-third of the world's population infected with latent TB. This is further aggravated by HIV coinfection and the emergence of multidrug- and extensively drug-resistant (MDR and XDR, respectively) TB; hence the quest for highly effective antitubercular drugs with novel modes of action is imperative. We report herein the discovery of an indole-2-carboxamide analogue, 3, as a highly potent antitubercular agent, and the subsequent chemical modifications aimed at establishing a preliminary body of structure activity relationships (SARs). These efforts led to the identification of three molecules (12-14) possessing an exceptional activity in the low nanomolar range against actively replicating Mycobacterium tuberculosis, with minimum inhibitory concentration (MIC) values lower than those of the most prominent antitubercular agents currently in use. These compounds were also devoid of apparent toxicity to Vero cells. Importantly, compound 12 was found to be active against the tested XDR-TB strains and orally active in the serum inhibition titration assay.

  DOI：

  10.1021/jm4003878
• 作为产物：
  描述：

  3,5-二甲基-1,2-苯二胺 在 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 4,6-dimethyl-1H-benzo[d]imidazole-2-carboxylic acid
  参考文献：
  名称：

  [EN] INHIBITORS OF DRUG-RESISTANT MYCOBACTERIUM TUBERCULOSIS
  [FR] INHIBITEURS DE MYCOBACTERIUM TUBERCULOSIS RÉSISTANT AUX MÉDICAMENTS

  摘要：

  本发明提供了用于治疗结核病的新型吲哚酰胺化合物，包括用于治疗耐药性M-结核病的药物，含有吲哚酰胺的组合物以及使用吲哚酰胺与其他生物活性剂联合治疗需求的受试者的结核病的方法。

  公开号：

  WO2015164482A1