4-phenyl-1-(4-methylsulfonylbenzoyl)thiosemicarbazide | 884651-74-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-phenyl-1-(4-methylsulfonylbenzoyl)thiosemicarbazide
• 英文别名: 1-[(4-Methylsulfonylbenzoyl)amino]-3-phenylthiourea
• CAS: 884651-74-5
• 化学式: C₁₅H₁₅N₃O₃S₂
• 分子量: 349.434
• InChiKey: VHGUTJKFDNMTTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-phenyl-1-(4-methylsulfonylbenzoyl)thiosemicarbazide 在 sodium hydroxide 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 生成 3-ethylsulfanyl-5-(4-methylsulfonylphenyl)-4-phenyl-1,2,4-triazole
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of substituted 3-alkylthio-4,5-diaryl-4H-1,2,4-triazoles as selective COX-2 inhibitors

  摘要：

  A new type of 4,5-diaryl-4H-1,2,4-triazole, possessing C-3 thio and alkylthio (SH, SMe or SEt) substituents was designed and synthesized for evaluation as selective cyclooxygenase-2 (COX-2) inhibitors with in vivo anti-inflarnmatory activity. The compound, 3-etilylthio-5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-4H-1,2,4-triazole (10d), exhibited a high in vitro selectivity (COX-1 IC50 = 20.5 nM; COX-2 IC50 = 1.8 nM; SI = 11.39) relative to the reference drug celecoxib (COX-1 IC50 = 3.7 nM; COX-2 IC50 = 2.2 nM; SI = 1.68) and also showed good anti-inflammatory activity compared to celecoxib in a carrageenan-induced rat paw edema assay. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.029
• 作为产物：
  描述：

  4-(methylsulfonyl)benzohydrazide 、 硫代异氰酸苯酯 以 乙醇 为溶剂， 反应 24.0h， 以86%的产率得到4-phenyl-1-(4-methylsulfonylbenzoyl)thiosemicarbazide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of substituted 3-alkylthio-4,5-diaryl-4H-1,2,4-triazoles as selective COX-2 inhibitors

  摘要：

  A new type of 4,5-diaryl-4H-1,2,4-triazole, possessing C-3 thio and alkylthio (SH, SMe or SEt) substituents was designed and synthesized for evaluation as selective cyclooxygenase-2 (COX-2) inhibitors with in vivo anti-inflarnmatory activity. The compound, 3-etilylthio-5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-4H-1,2,4-triazole (10d), exhibited a high in vitro selectivity (COX-1 IC50 = 20.5 nM; COX-2 IC50 = 1.8 nM; SI = 11.39) relative to the reference drug celecoxib (COX-1 IC50 = 3.7 nM; COX-2 IC50 = 2.2 nM; SI = 1.68) and also showed good anti-inflammatory activity compared to celecoxib in a carrageenan-induced rat paw edema assay. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.029

文献信息

• Design, synthesis, and biological evaluation of substituted 3-alkylthio-4,5-diaryl-4H-1,2,4-triazoles as selective COX-2 inhibitors
  作者：Latifeh Navidpour、Hamed Shafaroodi、Khosrou Abdi、Mohsen Amini、Mohammad H. Ghahremani、Ahmad Reza Dehpour、Abbas Shafiee

  DOI：10.1016/j.bmc.2005.11.029

  日期：2006.4

  A new type of 4,5-diaryl-4H-1,2,4-triazole, possessing C-3 thio and alkylthio (SH, SMe or SEt) substituents was designed and synthesized for evaluation as selective cyclooxygenase-2 (COX-2) inhibitors with in vivo anti-inflarnmatory activity. The compound, 3-etilylthio-5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-4H-1,2,4-triazole (10d), exhibited a high in vitro selectivity (COX-1 IC50 = 20.5 nM; COX-2 IC50 = 1.8 nM; SI = 11.39) relative to the reference drug celecoxib (COX-1 IC50 = 3.7 nM; COX-2 IC50 = 2.2 nM; SI = 1.68) and also showed good anti-inflammatory activity compared to celecoxib in a carrageenan-induced rat paw edema assay. (c) 2005 Elsevier Ltd. All rights reserved.