3-[(2-fluorophenyl)disulfanyl]-5-methyl-1H-1,2,4-triazole | 1393829-26-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-[(2-fluorophenyl)disulfanyl]-5-methyl-1H-1,2,4-triazole
• CAS: 1393829-26-9
• 化学式: C₉H₈FN₃S₂
• 分子量: 241.313
• InChiKey: VQKLRTBBNAOBTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  92.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-巯基-5-甲基-1,2,4-三氮唑 、 2-fluorophenylthiohypochlorite 以 乙醚 为溶剂， 反应 5.0h， 生成 3-[(2-fluorophenyl)disulfanyl]-5-methyl-1H-1,2,4-triazole
  参考文献：
  名称：

  Synthesis, Crystal Structure, in Vitro Acetohydroxyacid Synthase Inhibition, in Vivo Herbicidal Activity, and 3D-QSAR of New Asymmetric Aryl Disulfides

  摘要：

  Acetohydroxyacid synthase (AHAS; EC 2.2.1.6) is an important bioactive target for the design environmentally:., benign herbicides. On the basis of previous virtual screening, 50 asymmetric aryl disulfides containing [1,2,4]triazole groups were synthesized and characterized by H-1 NMR, HRMS, and crystal structure. Compounds I-a, I-b, and I-p show K-i values of 1.70, 4.69, and 5.57 mu M, respectively, for Wild type Arabidopsis thaliana AHAS (AtAHAS) and low resistance, against mutant type AtAHAS W574L. At 100 mg L-1 concentration, compounds. I-a, II-a, and II-b exhibit 86.6, 817, and 87.5% in vivo rape root growth inhibition. CoMFA steric and electrostatic contour maps were established, and a possible binding mode was suggested from molecular docking, which :provide valuable information to understand the key structural features. of these disulfide compounds. To the authors knowledge, this is the first comprehensive case suggesting that asymmetric aryl disulfides are novel AHAS inhibitors.

  DOI：

  10.1021/jf302206x