Methyl-<4-(4-methylbenzamido)phenyl>-sulfon | 73153-73-8

• 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: Methyl-<4-(4-methylbenzamido)phenyl>-sulfon
• 英文别名: N-(4-methylsulfonylphenyl)-4-methylbenzamide；Methyl-[4-(4-methylbenzamido)phenyl]-sulfon；4-methyl-N-(4-(methylsulfonyl)phenyl)benzamide；4-methyl-N-(4-methylsulfonylphenyl)benzamide
• CAS: 73153-73-8
• 化学式: C₁₅H₁₅NO₃S
• 分子量: 289.355
• InChiKey: NJFXYZJNRUJUKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  258-259 °C(Solv: methanol (67-56-1))
• 沸点：
  417.6±45.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl-<4-(4-methylbenzamido)phenyl>-sulfon 在 sodium hydroxide 、 五氯化磷 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 22.0h， 生成 4-(4-Methanesulfonyl-phenyl)-3-methylsulfanyl-5-p-tolyl-4H-[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-甲磺酰基苯胺 、 对甲基苯甲酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以96%的产率得到Methyl-<4-(4-methylbenzamido)phenyl>-sulfon
  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

• Heesing, Albert; Kleine Homann, Walter; Muellers, Wolfgang, Chemische Berichte, 1980, vol. 113, # 1, p. 152 - 164
  作者：Heesing, Albert、Kleine Homann, Walter、Muellers, Wolfgang

  DOI：——

  日期：——
• 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.