3-(4-chlorophenyl)-6-(4-fluorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-chlorophenyl)-6-(4-fluorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
• 化学式: C₁₆H₁₀ClFN₄S
• mdl: MFCD00268876
• 分子量: 344.8
• InChiKey: DCJHSDUAJLLDBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对氯苯甲酸甲酯 在 氢氧化钾 、 一水合肼 作用下， 以 乙醇 为溶剂， 生成 3-(4-chlorophenyl)-6-(4-fluorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
  参考文献：
  名称：

  Nadkarni; Kamat; Khadse, Arzneimittel-Forschung/Drug Research, 2001, vol. 51, # 7, p. 569 - 573

  摘要：

  DOI：

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.