[(4-Methylphenyl)sulfonylamino]methyl 4-methylbenzenesulfonate | 1416133-81-7

• 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-Methylphenyl)sulfonylamino]methyl 4-methylbenzenesulfonate
• 英文别名: [(4-methylphenyl)sulfonylamino]methyl 4-methylbenzenesulfonate
• CAS: 1416133-81-7
• 化学式: C₁₅H₁₇NO₅S₂
• 分子量: 355.436
• InChiKey: HVUJSDPDSBABTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(4-Methylphenyl)sulfonylamino]methyl 4-methylbenzenesulfonate 在 sodium azide 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 1-[(p-toluenesulfonamido)methyl]-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：

  氨基甲醇 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 [(4-Methylphenyl)sulfonylamino]methyl 4-methylbenzenesulfonate
  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

文献信息

• Copper-mediated intramolecular aminofluorination of 1,3-dienes by using nucleophilic fluorine reagents
  作者：Zuxiao Zhang、Pinhong Chen、Guosheng Liu

  DOI：10.1039/c8cc04909b

  日期：——

  A copper-mediated intramolecular aminofluorination of 1,3-dienes is disclosed, in which both AgF and Et3N·3HF can be used as the fluorine source. This protocol provides a variety of pyrrolidines bearing allylic fluorides with excellent regioselectivities and good diastereoselectivities.

  公开了铜介导的1，3-二烯的分子内氨基氟化，其中AgF和Et 3 N·3HF都可以用作氟源。该协议提供了多种带有烯丙基氟化物的吡咯烷，它们具有极好的区域选择性和良好的非对映选择性。