4-amino-5-(3-fluoropyridin-4-yl)-3-mercapto-1,2,4-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-amino-5-(3-fluoropyridin-4-yl)-3-mercapto-1,2,4-triazole
• 英文别名: 4-amino-3-(3-fluoropyridin-4-yl)-1H-1,2,4-triazole-5-thione
• 化学式: C₇H₆FN₅S
• 分子量: 211.223
• InChiKey: KMQUFJRCEDDNOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-硝基苯氧乙酸 、 4-amino-5-(3-fluoropyridin-4-yl)-3-mercapto-1,2,4-triazole 在 4-二甲氨基吡啶 、 四丁基溴化铵 、 三氯氧磷 作用下， 以95%的产率得到3-(3-fluoropyridin-4-yl)-6-((4-nitrophenoxy)methyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
  参考文献：
  名称：

  SAR studies on 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles as inhibitors of Mtb shikimate dehydrogenase for the development of novel antitubercular agents

  摘要：

  三唑噻二唑是一种具有较强抗结核活性的药物，对MtSD有适度的抑制作用，并且没有明显的细胞毒性。

  DOI：

  10.1039/c5ra19334f
• 作为产物：
  描述：

  3-氟吡啶-4-甲酸 在 一水合肼 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 4-amino-5-(3-fluoropyridin-4-yl)-3-mercapto-1,2,4-triazole
  参考文献：
  名称：

  SAR studies on 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles as inhibitors of Mtb shikimate dehydrogenase for the development of novel antitubercular agents

  摘要：

  三唑噻二唑是一种具有较强抗结核活性的药物，对MtSD有适度的抑制作用，并且没有明显的细胞毒性。

  DOI：

  10.1039/c5ra19334f

文献信息

• Preliminary SAR and biological evaluation of antitubercular triazolothiadiazine derivatives against drug-susceptible and drug-resistant Mtb strains
  作者：Ziqiang Li、Xiaoguang Bai、Qi Deng、Guoning Zhang、Lei Zhou、Yishuang Liu、Juxian Wang、Yucheng Wang

  DOI：10.1016/j.bmc.2016.10.027

  日期：2017.1

  Following up the SAR study of triazolothiadiazoles for their antitubercular activities targeting Mt SD in our previous study, on the principle of scaffold hopping, the C3 and C6 positions of triazolothiadiazine were examined systematically to define a preliminary structure-activity relationship (SAR) with respect to biological activity. This study herein highlights the potential of two highly potent advanced leads 6c-3, 6g-3 and several other compounds with comparable potencies as promising new candidates for the treatment of TB (6c-3, MIC-H37Rv = 0.25 mu g/mL; MIC-MDRTB = 2.0 mu g/mL; MIC-RDRTB = 0.25 mu g/mL; Mt SD-IC50 = 86.39 mu g/mL; and 6g-3, MIC-H37Rv = 1.0 mu g/mL; MIC-MDRTB = 4.0 mu g/mL; MICRDRTB = 2.0 mu g/mL; Mt SD-IC50 = 73.57 mu g/mL). Compounds 6c-3 and 6g-3 possessed a para-nitro phenyl at the 6 position showed low Vero and HepG2 cells toxicity, turning out to be two excellent lead candidates for preclinical trials. In addition, in vitro Mt SD inhibitory assay indicates that Mt SD is at least one of the targets for their antitubercular activity. Thus, they may turn out to be promising multidrug-resistance- reversing agents. (C) 2016 Elsevier Ltd. All rights reserved.
• SAR studies on 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles as inhibitors of Mtb shikimate dehydrogenase for the development of novel antitubercular agents
  作者：Ziqiang Li、Yishuang Liu、Xiaoguang Bai、Qi Deng、Juxian Wang、Guoning Zhang、Chunling Xiao、Yaning Mei、Yucheng Wang

  DOI：10.1039/c5ra19334f

  日期：——

  Triazolothiadiazoles are potent antitubercular agents with modest inhibitory forMtSD and without appreciable cytotoxicity.

  三唑噻二唑是一种具有较强抗结核活性的药物，对MtSD有适度的抑制作用，并且没有明显的细胞毒性。