2-((Ethanesulfonyl)amino)ethyl-1-ethanesulfonate | 320601-53-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-((Ethanesulfonyl)amino)ethyl-1-ethanesulfonate
• 英文别名: 2-(Ethylsulfonylamino)ethyl ethanesulfonate
• CAS: 320601-53-4
• 化学式: C₆H₁₅NO₅S₂
• 分子量: 245.321
• InChiKey: NYUITCUMXCALED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-((Ethanesulfonyl)amino)ethyl-1-ethanesulfonate 在 sodium azide 作用下， 反应 6.0h， 生成 N-(2-azidoethyl)ethanesulfonamide
  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：

  C.I.酸性橙108 、 乙基磺酰氯 以 吡啶 、 二氯甲烷 为溶剂， 以12%的产率得到2-((Ethanesulfonyl)amino)ethyl-1-ethanesulfonate
  参考文献：
  名称：

  New 4-arylpiperidine derivatives for the treatment of pruritus

  摘要：

  提供了一种公式I的化合物，其中Het1、R1、R2、R3、X和n具有说明书中给出的含义，它们在通过阿片受体介导的疾病的预防和治疗中是有用的，例如瘙痒。

  公开号：

  US20030004340A1

文献信息

• New 4-arylpiperidine derivatives for the treatment of pruritus
  申请人：——

  公开号：US20030004340A1

  公开（公告）日：2003-01-02

  There is provided a compound of formula I, 1 wherein Het 1 , R 1 , R 2 , R 3 , X and n have meanings given in the description, which are useful in the prophylaxis and in the treatment of diseases mediated by opiate receptors, such as pruritus.

  提供了一种公式I的化合物，其中Het1、R1、R2、R3、X和n具有说明书中给出的含义，它们在通过阿片受体介导的疾病的预防和治疗中是有用的，例如瘙痒。
• 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.