3-Nitro-4-[[2-(phenylthio)ethyl]amino]benzenesulfonyl azide | 1069135-23-4

• 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: 3-Nitro-4-[[2-(phenylthio)ethyl]amino]benzenesulfonyl azide
• 英文别名: N-diazo-3-nitro-4-(2-phenylsulfanylethylamino)benzenesulfonamide
• CAS: 1069135-23-4
• 化学式: C₁₄H₁₃N₅O₄S₂
• 分子量: 379.42
• InChiKey: JOUBAVABKSFPHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  硫代苯甲酸 、 3-Nitro-4-[[2-(phenylthio)ethyl]amino]benzenesulfonyl azide 在 2,6-二甲基吡啶 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以54%的产率得到N-[3-nitro-4-(2-phenylsulfanylethylamino)phenyl]sulfonylbenzamide
  参考文献：
  名称：

  [EN] ACYLSULFONAMIDES AND PROCESSES FOR PRODUCING THE SAME
  [FR] ACYLSULFONAMIDES ET PROCÉDÉS POUR PRODUIRE CEUX-CI

  摘要：

  公开号：

  WO2012021486A3
• 作为产物：
  描述：

  4-氟-3-硝基苯磺酰氯 在 sodium azide 、 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 3-Nitro-4-[[2-(phenylthio)ethyl]amino]benzenesulfonyl azide
  参考文献：
  名称：

  [EN] ACYLSULFONAMIDES AND PROCESSES FOR PRODUCING THE SAME
  [FR] ACYLSULFONAMIDES ET PROCÉDÉS POUR PRODUIRE CEUX-CI

  摘要：

  公开号：

  WO2012021486A3

文献信息

• Sulfo-click reaction via in situ generated thioacids and its application in kinetic target-guided synthesis
  作者：Niranjan Kumar Namelikonda、Roman Manetsch

  DOI：10.1039/c1cc14724b

  日期：——

  Herein, we describe a practical, one-pot variant of the sulfo-click reaction, in which 9-fluorenylmethyl-protected thioesters are rapidly deprotected and reacted further with sulfonylazides to give N-acyl sulfonamides.

  在此，我们描述了一种实用的硫-点击反应单锅变体，其中带有9-芴基甲基保护的硫酯迅速去保护，并与磺酰叠氮物进一步反应，生成N-酰基磺酰胺。
• Bcl-X_L-Templated Assembly of Its Own Protein−Protein Interaction Modulator from Fragments Decorated with Thio Acids and Sulfonyl Azides
  作者：Xiangdong Hu、Jiazhi Sun、Hong-Gang Wang、Roman Manetsch

  DOI：10.1021/ja802683u

  日期：2008.10.22

  Protein-protein interactions have key importance in various biological processes and modulation of particular protein-protein interactions has been shown to have therapeutic effects. However, disrupting or modulating protein-protein interactions with low-molecular-weight compounds is extremely difficult due to the lack of deep binding pockets on protein surfaces. Herein we describe the development of an unprecedented lead synthesis and discovery method that generated only biologically active compounds from a library of reactive fragments. Using the protein Bcl-X-L, a central regulator of programmed cell death, we demonstrated that an amidation reaction between thio acids and sulfonyl azides is applicable for Bcl-X-L-templated assembly of inhibitory compounds. We have demonstrated for the first time that kinetic target guided synthesis can be applied not only on enzymatic targets but also for the discovery of small molecules modulating protein-protein interactions.
• Acylsulfonamides and Processes for Producing the Same
  申请人：Manetsch Roman

  公开号：US20110130568A1

  公开（公告）日：2011-06-02

  The present disclosure relates to acylsulfonamides and processes for their preparation. The processes involve a target-guided synthesis approach, whereby a thioacid and a sulfonyl azide are reacted in the presence of a biological target protein, a Bcl-2 family protein, to form the acylsulfonamide.
• ACYLSULFONAMIDES AND PROCESSES FOR PRODUCING THE SAME
  申请人：Manetsch Roman

  公开号：US20130203709A1

  公开（公告）日：2013-08-08

  The present disclosure relates to acylsulfonamides and processes for their preparation. The processes involve a target-guided synthesis approach, whereby a thioacid and a sulfonyl azide are reacted in the presence of a biological target protein, a Bcl-2 family protein, to form the acylsulfonamide.
• Target Binding Molecules Identified by Kinetic Target-Guided Synthesis
  申请人：UNIVERSITY OF SOUTH FLORIDA (A FLORIDA NON-PROFIT CORPORATION)

  公开号：US20160116482A1

  公开（公告）日：2016-04-28

  Methods of identifying target binding molecules by target guided synthesis are provided. The methods include providing two or more fragments capable of reacting to form the target binding molecule and mixing the fragments with the target. The methods can be used to identify target binding molecules that bind targets such as proteins or nucleic acids, including those that bind shallow binding pockets on the surface of such targets. The methods are applied to the Bcl-XL and Mcl-1 proteins from the Bcl-2 family of proteins. Using thio acid and sulfonyl azide fragments capable of reacting through sulfo-click chemistry, new acyl sulfonamides are identified that bind one or both of the Bcl-XL and Mcl-1 proteins. Pharmaceutical formulations of these target binding molecules are also provided.