5-(4-methoxyphenyl)-1-(4-(methylsulfonyl)phenyl)-1H-1,2,3-triazole | 1126642-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-methoxyphenyl)-1-(4-(methylsulfonyl)phenyl)-1H-1,2,3-triazole
• 英文别名: 5-(4-methoxyphenyl)-1-(4-methylsulfonylphenyl)triazole
• CAS: 1126642-07-6
• 化学式: C₁₆H₁₅N₃O₃S
• 分子量: 329.379
• InChiKey: ZNJHGPCAFLJJHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-azido-4-(methylsulfonyl)benzene 、 4-乙炔基苯甲醚 在 五甲基环戊二烯基双(三苯基膦)氯化钌(II) 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以16%的产率得到5-(4-methoxyphenyl)-1-(4-(methylsulfonyl)phenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis and cyclooxygenase inhibition of various (aryl-1,2,3-triazole-1-yl)-methanesulfonylphenyl derivatives

  摘要：

  A series of 1,4- and 1,5-diaryl substituted 1,2,3-triazoles was synthesized by either Cu( I)-catalyzed or Ru( II)-catalyzed 1,3-dipolar cycloaddition reactions between 1-azido-4-methane-sulfonylbenzene 9 and a panel of various para-substituted phenyl acetylenes ( 4- H, 4- Me, 4- OMe, 4- NMe2, 4- Cl, 4- F). All compounds were used in in vitro cyclooxygenase ( COX) assays to determine the combined electronic and steric effects upon COX-1 and COX-2 inhibitory potency and selectivity. Structure-activity relationship studies showed that compounds having a vicinal diaryl substitution pattern showed more potent COX-2 inhibition (IC50 = 0.03-0.36 mu M) compared to their corresponding 1,3-diaryl-substituted counterparts (IC50 = 0.15 to > 10.0 mu M). In both series, compounds possessing an electron-withdrawing group ( Cl and F) at the para-position of one of the aryl rings displayed higher COX-2 inhibition potency and selectivity as determined for compounds containing electron-donating groups ( Me, OMe, NMe2). The obtained data show, that the central carbocyclic or heterocyclic ring system as found in many COX-2 inhibitors can be replaced by a central 1,2,3-triazole unit without losing COX-2 inhibition potency and selectivity. The high COX-2 inhibition potency of some 1,2,3-triazoles having a vicinal diaryl substitution pattern along with their ease in synthesis through versatile Ru( II)-catalyzed click chemistry make this class of compounds interesting candidates for further design and synthesis of highly selective and potent COX-2 inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.032

文献信息

• Synthesis and cyclooxygenase inhibition of various (aryl-1,2,3-triazole-1-yl)-methanesulfonylphenyl derivatives
  作者：Frank Wuest、Xinli Tang、Torsten Kniess、Jens Pietzsch、Mavanur Suresh

  DOI：10.1016/j.bmc.2008.12.032

  日期：2009.2

  A series of 1,4- and 1,5-diaryl substituted 1,2,3-triazoles was synthesized by either Cu( I)-catalyzed or Ru( II)-catalyzed 1,3-dipolar cycloaddition reactions between 1-azido-4-methane-sulfonylbenzene 9 and a panel of various para-substituted phenyl acetylenes ( 4- H, 4- Me, 4- OMe, 4- NMe2, 4- Cl, 4- F). All compounds were used in in vitro cyclooxygenase ( COX) assays to determine the combined electronic and steric effects upon COX-1 and COX-2 inhibitory potency and selectivity. Structure-activity relationship studies showed that compounds having a vicinal diaryl substitution pattern showed more potent COX-2 inhibition (IC50 = 0.03-0.36 mu M) compared to their corresponding 1,3-diaryl-substituted counterparts (IC50 = 0.15 to > 10.0 mu M). In both series, compounds possessing an electron-withdrawing group ( Cl and F) at the para-position of one of the aryl rings displayed higher COX-2 inhibition potency and selectivity as determined for compounds containing electron-donating groups ( Me, OMe, NMe2). The obtained data show, that the central carbocyclic or heterocyclic ring system as found in many COX-2 inhibitors can be replaced by a central 1,2,3-triazole unit without losing COX-2 inhibition potency and selectivity. The high COX-2 inhibition potency of some 1,2,3-triazoles having a vicinal diaryl substitution pattern along with their ease in synthesis through versatile Ru( II)-catalyzed click chemistry make this class of compounds interesting candidates for further design and synthesis of highly selective and potent COX-2 inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.