(S)-2-amino-N-[1-(4-tert-butylphenyl)-1H-4,5,6,7-tetrahydroindazol-4-yl]-4-methylsulfanylbutyramide trifluoroacetate | 1203661-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-2-amino-N-[1-(4-tert-butylphenyl)-1H-4,5,6,7-tetrahydroindazol-4-yl]-4-methylsulfanylbutyramide trifluoroacetate
• CAS: 1203661-67-9
• 化学式: C₂HF₃O₂*C₂₂H₃₂N₄OS
• 分子量: 514.612
• InChiKey: OZNBGGMVOYGWEB-HMEPSURWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  110.24
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-N-[1-(4-tert-butylphenyl)-1H-4,5,6,7-tetrahydroindazol-4-yl]-4-methylsulfanylbutyramide trifluoroacetate 、 三氟乙酸 生成 (S)-2-amino-N-[1-(4-tert-butylphenyl)-1H-4,5,6,7-tetrahydroindazol-4-yl]-4-methylsulfanylbutyramide
  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
• 作为产物：
  描述：

  L-蛋氨酸 、 1-(4-(tert-Butyl)phenyl)-4,5,6,7-tetrahydro-1H-indazol-4-amine 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-2-amino-N-[1-(4-tert-butylphenyl)-1H-4,5,6,7-tetrahydroindazol-4-yl]-4-methylsulfanylbutyramide trifluoroacetate
  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