3,6-bis(2,4-dichloro-5-fluorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine | 1135234-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,6-bis(2,4-dichloro-5-fluorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
• CAS: 1135234-43-3
• 化学式: C₁₆H₆Cl₄F₂N₄S
• 分子量: 466.125
• InChiKey: DYGWFOIIUPEKNB-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C(Solvent: Ethanol; 1,4-Dioxane)
• 沸点：
  608.7±65.0 °C(predicted)
• 密度：
  1.80±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 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：
  6

反应信息

• 作为反应物：
  描述：

  3,6-bis(2,4-dichloro-5-fluorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 、 苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 7-benzylidene-3,6-bis(2,4-dichloro-5-fluorophenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine
  参考文献：
  名称：

  Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines

  摘要：

  2,4-Dichloro-5-fluorophenyl containing 7-arylidenetriazolothiadiazines were obtained by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with 2,3-dibromo-1,3-diarylpropan-1-ones, and also by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with alpha-bromopropenones in the presence of a base. The structure of the 7-arylidenetriazolothiadiazines was confirmed by an alternative synthesis. A plausible mechanism for the formation of 7-arylidenetriazolothiadiazines is proposed. All newly synthesized compounds were screened for their analgesic and antimicrobial activities. Compounds bearing 4-chlorophenyl or 3,4-methylenedioxyphenyl moieties at position 7 of the arylidenetriazolothiadiazines showed excellent analgesic activity. Arylidenetriazolothiadiazines carrying a phenyl, 4-chlorophenyl, 4-methylphenyl, 3,4-dimethoxyphenyl, and 2,4-dichlorophenyl moieties at position 7 showed excellent antibacterial and antifungal activities.

  DOI：

  10.1007/s00706-007-0797-9
• 作为产物：
  描述：

  4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole 、 α-bromo-(2,4-dichloro-5-fluoro)acetophenone 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以74%的产率得到3,6-bis(2,4-dichloro-5-fluorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
  参考文献：
  名称：

  Synthesis and antitumor activity studies of some new fused 1,2,4-triazole derivatives carrying 2,4-dichloro-5-fluorophenyl moiety

  摘要：

  A series of 3-(2,4-dichloro-5-fluorophenyl)-6-(substituted phenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (4) (Fig. 1) have been synthesized by the cyclization of 3-(2,4-dichloro-5-fluorophenyl)-1,2,4-triazol-5-thiol (3) with substituted phenacyl bromides. All the newly synthesized compounds were confirmed by IR, H-1 NMR and mass spectral studies. Among the compounds tested for their antitumor activity three compounds exhibited in vitro antitumor activity with moderate to excellent growth inhibition against a panel of sixty cancer cell lines of leukemia, non-small cell lung cancer, melanoma, ovarian cancer, prostate and breast cancer. The compound 4d showed promising antiproliferative activity with GI(50) values in the range of 1.06-25.4 mu M. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.09.010