[2-(trifluoromethyl)phenylsulfonyl]aminoethyl 2-trifluoromethylphenylsulfonate | 1073562-12-5

• 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: [2-(trifluoromethyl)phenylsulfonyl]aminoethyl 2-trifluoromethylphenylsulfonate
• 英文别名: 2-(2-trifluoromethylphenyl)sulfonylaminoethyl 2-trifluoromethylphenylsulfonate；2-[[2-(Trifluoromethyl)phenyl]sulfonylamino]ethyl 2-(trifluoromethyl)benzenesulfonate；2-[[2-(trifluoromethyl)phenyl]sulfonylamino]ethyl 2-(trifluoromethyl)benzenesulfonate
• CAS: 1073562-12-5
• 化学式: C₁₆H₁₃F₆NO₅S₂
• 分子量: 477.405
• InChiKey: ZURUYIRNZBMXOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [2-(trifluoromethyl)phenylsulfonyl]aminoethyl 2-trifluoromethylphenylsulfonate 在 sodium azide 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 1-{2-[2-(trifluoromethane)phenylsulfonamido]ethyl}-1H-1,2,3-triazole-4,5-dicarboxylic acid
  参考文献：
  名称：

  Fragment-based discovery of novel and selective mPGES-1 inhibitors Part 1: Identification of sulfonamido-1,2,3-triazole-4,5-dicarboxylic acid

  摘要：

  Microsomal prostaglandin E synthase-1 (mPGES-1) is an inducible prostaglandin E synthase that catalyzes the conversion of prostaglandin PGH(2) to PGE(2) and represents a novel target for therapeutic treatment of inflammatory disorders. It is essential to identify mPGES-1 inhibitor with novel scaffold as new hit or lead compound for the purpose of the next-generation anti-inflammatory drugs. Herein we report the discovery of sulfonamido-1,2,3-triazole-4,5-dicarboxylic derivatives as a novel class of mPGES-1 inhibitors identified through fragment-based virtual screening and in vitro assays on the inhibitory activity of the actual compounds. 1-[2-(N-Phenylbenzenesulfonamido)ethyl]-1H-1,2,3-triazole-4,5-dicarboxylic acid (6f) inhibits human mPGES-1 (IC50 of 1.1 mu M) with high selectivity (ca. 1000-fold) over both COX-1 and COX-2 in a cell-free assay. In addition, the activity of compound 6f was again tested at 10 mu M concentration in presence of 0.1% Triton X-100 and found to be reduced to 1/4 of its original activity without this detergent. Compared to the complete loss of activity of nuisance inhibitor with the detergent, therefore, compound 6f would be regarded as a partial nuisance inhibitor of mPGES-1 with a novel scaffold for the optimal design of more potent mPGES-1 inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.019
• 作为产物：
  描述：

  2-三氟甲基苯磺酰氯 、 C.I.酸性橙108 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到[2-(trifluoromethyl)phenylsulfonyl]aminoethyl 2-trifluoromethylphenylsulfonate
  参考文献：
  名称：

  基于19F NMR的pH探针：具有pH敏感化学位移的镧系元素（III）配合物。

  摘要：

  给出了几种镧系元素与四氮杂十二烷衍生物作为19 F NMR化学位移pH探针的实验测量和磁性能，结构动力学和酸碱平衡的理论分析；pKa值在6.9到7.7之间变化，酸性和碱性形式的Ho（III）配合物的T1值在10到30毫秒（4.7-9.4 T，295 K）之间，化学位移相差18到40 ppm。

  DOI：

  10.1039/b802838a

文献信息

• WO2008/132433
  申请人：——

  公开号：——

  公开（公告）日：——
• Fragment-based discovery of novel and selective mPGES-1 inhibitors Part 1: Identification of sulfonamido-1,2,3-triazole-4,5-dicarboxylic acid
  作者：Kijae Lee、Van Chung Pham、Min Ji Choi、Kyung Ju Kim、Kyung-Tae Lee、Seong-Gu Han、Yeon Gyu Yu、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2012.11.019

  日期：2013.1

  Microsomal prostaglandin E synthase-1 (mPGES-1) is an inducible prostaglandin E synthase that catalyzes the conversion of prostaglandin PGH(2) to PGE(2) and represents a novel target for therapeutic treatment of inflammatory disorders. It is essential to identify mPGES-1 inhibitor with novel scaffold as new hit or lead compound for the purpose of the next-generation anti-inflammatory drugs. Herein we report the discovery of sulfonamido-1,2,3-triazole-4,5-dicarboxylic derivatives as a novel class of mPGES-1 inhibitors identified through fragment-based virtual screening and in vitro assays on the inhibitory activity of the actual compounds. 1-[2-(N-Phenylbenzenesulfonamido)ethyl]-1H-1,2,3-triazole-4,5-dicarboxylic acid (6f) inhibits human mPGES-1 (IC50 of 1.1 mu M) with high selectivity (ca. 1000-fold) over both COX-1 and COX-2 in a cell-free assay. In addition, the activity of compound 6f was again tested at 10 mu M concentration in presence of 0.1% Triton X-100 and found to be reduced to 1/4 of its original activity without this detergent. Compared to the complete loss of activity of nuisance inhibitor with the detergent, therefore, compound 6f would be regarded as a partial nuisance inhibitor of mPGES-1 with a novel scaffold for the optimal design of more potent mPGES-1 inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.
• 19F NMR based pH probes: lanthanide(iii) complexes with pH-sensitive chemical shifts
  作者：Alan M. Kenwright、Ilya Kuprov、Elena De Luca、David Parker、Shashi U. Pandya、P. Kanthi Senanayake、David G. Smith

  DOI：10.1039/b802838a

  日期：——

  properties, structural dynamics and acid-base equilibria for several lanthanide(III) complexes with tetraazacyclododecane derivatives as 19F NMR chemical shift pH probes are presented; pKa values vary between 6.9 and 7.7, with 18 to 40 ppm chemical shift differences between the acidic and basic forms for Ho(III) complexes possessing T1 values of 10 to 30 ms (4.7-9.4 T, 295 K).

  给出了几种镧系元素与四氮杂十二烷衍生物作为19 F NMR化学位移pH探针的实验测量和磁性能，结构动力学和酸碱平衡的理论分析；pKa值在6.9到7.7之间变化，酸性和碱性形式的Ho（III）配合物的T1值在10到30毫秒（4.7-9.4 T，295 K）之间，化学位移相差18到40 ppm。