1-[4-[4-Bromo-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonyl-3-phenylthiourea | 1274724-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[4-[4-Bromo-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonyl-3-phenylthiourea
• CAS: 1274724-44-5
• 化学式: C₁₈H₁₄BrF₃N₄O₂S₂
• 分子量: 519.366
• InChiKey: UHDQATKEHAPJPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[4-[4-Bromo-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonyl-3-phenylthiourea 在 哌啶 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 4-[4-bromo-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-N-(3,6-diphenyl-3,3a-dihydro-2H-pyrazolo[3,4-d][1,3]thiazol-5-ylidene)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and biological evaluation of new 3-trifluoromethylpyrazolesulfonyl-urea and thiourea derivatives as antidiabetic and antimicrobial agents

  摘要：

  Fluorinated pyrazoles, and benzenesulfonylurea and thiourea derivatives as well as their cyclic sulfonylthioureas 2-18 were prepared as hypoglycemic and antibacterial agents. The chemistry involves the condensation of 4-hydrazino benzenesulfonamide hydrochloride with 1-trifluoromethyl diketones 1 to give pyrazole derivatives 2 which upon bromination gave the bromopyrazole 3. Reaction of 2 or 3 with isocyanates and isothiocyanates gave the corresponding ureas 4 and 5 and thioureas 6 and 7. Cyclization of thiourea derivatives with ethyl bromoacetate, ethyl beta-bromopropionate, 1,3-dichloroacetone and alpha-bromoacetophenone yielded the corresponding 4-oxothiazolidines 8 and 9, 4-oxo-5,6-dihydrothiazine 10, 5-oxo-4,5-dihydrothiazines 11 and 12 and thiazolines 13 and 14. Preliminary biological screening of the prepared compounds revealed significant antidiabetic and antibacterial activities. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.12.009
• 作为产物：
  描述：

  4-磺酰胺基苯肼盐酸盐 在 溴 、 potassium carbonate 作用下， 以 乙醇 、 氯仿 、 丙酮 为溶剂， 反应 15.0h， 生成 1-[4-[4-Bromo-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonyl-3-phenylthiourea
  参考文献：
  名称：

  Synthesis and biological evaluation of new 3-trifluoromethylpyrazolesulfonyl-urea and thiourea derivatives as antidiabetic and antimicrobial agents

  摘要：

  Fluorinated pyrazoles, and benzenesulfonylurea and thiourea derivatives as well as their cyclic sulfonylthioureas 2-18 were prepared as hypoglycemic and antibacterial agents. The chemistry involves the condensation of 4-hydrazino benzenesulfonamide hydrochloride with 1-trifluoromethyl diketones 1 to give pyrazole derivatives 2 which upon bromination gave the bromopyrazole 3. Reaction of 2 or 3 with isocyanates and isothiocyanates gave the corresponding ureas 4 and 5 and thioureas 6 and 7. Cyclization of thiourea derivatives with ethyl bromoacetate, ethyl beta-bromopropionate, 1,3-dichloroacetone and alpha-bromoacetophenone yielded the corresponding 4-oxothiazolidines 8 and 9, 4-oxo-5,6-dihydrothiazine 10, 5-oxo-4,5-dihydrothiazines 11 and 12 and thiazolines 13 and 14. Preliminary biological screening of the prepared compounds revealed significant antidiabetic and antibacterial activities. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.12.009