O,N-bisbenzenesulfonyl-N-methylethanolamine | 85753-64-6

• 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: O,N-bisbenzenesulfonyl-N-methylethanolamine
• 英文别名: 2-[Benzenesulfonyl(methyl)amino]ethyl benzenesulfonate；2-[benzenesulfonyl(methyl)amino]ethyl benzenesulfonate
• CAS: 85753-64-6
• 化学式: C₁₅H₁₇NO₅S₂
• 分子量: 355.436
• InChiKey: UAUIAMKQSBXDDS-UHFFFAOYSA-N

物化性质

• 沸点：
  523.2±52.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  97.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O,N-bisbenzenesulfonyl-N-methylethanolamine 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 N-[3-(3,4-Dimethoxy-phenyl)-4-oxo-butyl]-N-methyl-benzenesulfonamide
  参考文献：
  名称：

  Sceletium（aizoaceae）生物碱：外消旋甲磺拉酮，茹伯汀胺和表柔伯汀胺的全合成

  摘要：

  所述的全合成Sceletium生物碱mesembranone，joubertinamine和epijoubertinamine经由烯酮的分子内环化到benzensulfo酰胺溶解金属还原的条件下分组进行说明。

  DOI：

  10.1016/s0040-4039(00)81461-6
• 作为产物：
  描述：

  N-甲基-2-羟基乙胺 、 苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 O,N-bisbenzenesulfonyl-N-methylethanolamine
  参考文献：
  名称：

  Sceletium（aizoaceae）生物碱：外消旋甲磺拉酮，茹伯汀胺和表柔伯汀胺的全合成

  摘要：

  所述的全合成Sceletium生物碱mesembranone，joubertinamine和epijoubertinamine经由烯酮的分子内环化到benzensulfo酰胺溶解金属还原的条件下分组进行说明。

  DOI：

  10.1016/s0040-4039(00)81461-6

文献信息

• Sceletium (aizoaceae) alkaloids: total synthesis of racemic mesembranone, joubertinamine and epijoubertinamine
  作者：Ignacio H. Sánchez、José de Jesús Soria、María Isabel Larraza、Humberto J. Flores

  DOI：10.1016/s0040-4039(00)81461-6

  日期：1983.1

  The total synthesis of the Sceletium alkaloids mesembranone, joubertinamine and epijoubertinamine via the intramolecular cyclization of an enone to a benzensulfo amide grouping under the conditions of a dissolving metal reduction is described.

  所述的全合成Sceletium生物碱mesembranone，joubertinamine和epijoubertinamine经由烯酮的分子内环化到benzensulfo酰胺溶解金属还原的条件下分组进行说明。
• 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.
• Sanchez, I. H.; Larraza, M. I.; Flores, H. J., Synthetic Communications, 1983, vol. 13, # 1, p. 35 - 41
  作者：Sanchez, I. H.、Larraza, M. I.、Flores, H. J.、Rojas, I.、Alcala, R.

  DOI：——

  日期：——