N-[1-(4-tert-butylphenyl)-1H-indazol-4-yl]-2,1,3-benzoxadiazole-5-carboxamide 1-oxide | 1203662-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[1-(4-tert-butylphenyl)-1H-indazol-4-yl]-2,1,3-benzoxadiazole-5-carboxamide 1-oxide
• 英文别名: N-[1-(4-tert-butylphenyl)indazol-4-yl]-1-oxido-2,1,3-benzoxadiazol-1-ium-5-carboxamide
• CAS: 1203662-03-6
• 化学式: C₂₄H₂₁N₅O₃
• 分子量: 427.462
• InChiKey: NLCAUSUXWPTRCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  98.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-tert-butylphenyl)-4-amino-1H-indazole 、 苯并氧化呋咱-5-羧酸 在 4-二甲氨基吡啶 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以21%的产率得到N-[1-(4-tert-butylphenyl)-1H-indazol-4-yl]-2,1,3-benzoxadiazole-5-carboxamide 1-oxide
  参考文献：
  名称：

  Identification, Synthesis, and Pharmacological Evaluation of Tetrahydroindazole Based Ligands as Novel Antituberculosis Agents

  摘要：

  The resurgence Of tuberculosis (TB), the incidence of drug-resistant strains of Mycobacterium tuberculosis (MTB), and the coinfection between TB and HIV have led to serious infections, high mortality, and it global health threat, resulting in the urgent search for new classes of antimycobacterial agents. Herein, we report the identification of a novel class of tetrahydroindazole based compounds as potent and unique inhibitors of MTB. Compounds 6a, 6m, and 6q exhibited activity in the low micromolar range against replicating Mycobacterium tuberculosis (R-TB) phenotype, with minimum inhibitory concentrations (MICs) of 1.7, 1.9, and 1.9 mu M, respectively, while showing no toxicity to Vero Ccells, Moreover, studies aimed to assess the in vitro metabolic stability of 6a and 6m in mouse liver microsomes and in vivo pharmacokinetic profiles in plasma levels gave satisfactory results. This research suggests that tetrahydroindazole based anti-TB compounds can serve its a promising lead scaffold in developing new drugs to combat tuberculosis infections.

  DOI：

  10.1021/jm901235p