4-(bromomethyl)benzenesulfonyl azide | 1069135-16-5

• 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: 4-(bromomethyl)benzenesulfonyl azide
• 英文别名: 4-(bromomethyl)-N-diazobenzenesulfonamide
• CAS: 1069135-16-5
• 化学式: C₇H₆BrN₃O₂S
• 分子量: 276.114
• InChiKey: IHWSOBCKLRCRNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(bromomethyl)benzenesulfonyl azide 在 4-二甲氨基吡啶 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成 4-(((4-(N-(3,5-dimethoxybenzoyl)sulfamoyl)benzyl)(2-(phenylthio)ethyl)amino)methyl)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
• 作为产物：
  描述：

  4-溴甲基苯磺酰氯 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 生成 4-(bromomethyl)benzenesulfonyl azide
  参考文献：
  名称：

  超越二元：使用多片段动力学目标引导合成方法快速鉴定蛋白质-蛋白质相互作用调节剂

  摘要：

  动力学靶标引导合成 (KTGS) 是一种强大的筛选方法，能够识别生物分子的小分子调节剂。虽然已经出现了许多 KTGS 变体，但大多数示例都受到吞吐量有限和信噪比较差的影响，从而妨碍了可靠的命中检测。在此，我们提出了解决这些限制的优化多片段 KTGS 筛选策略。该方法利用选定的反应监测液相色谱串联质谱法进行命中检测，从而能够在每个筛选孔中孵育 190 个片段组合。因此，我们的片段库从 81 个可能的组合扩展到 1710 个，代表迄今为止组装的最大的 KTGS 筛选库。对扩展的文库进行了针对 Mcl-1 的筛选，最终发现了 24 种抑制剂。这项工作揭示了 KTGS 在快速、可靠地鉴定命中物方面的真正潜力，进一步凸显了其作为药物发现中现有筛选方法的补充的实用性。

  DOI：

  10.1021/acs.jmedchem.3c00108

文献信息

• Cycloaddition of <i>N</i>-sulfonyl and <i>N</i>-sulfamoyl azides with alkynes in aqueous media for the selective synthesis of 1,2,3-triazoles
  作者：Thumpati Prasanth、Gargi Chakraborti、Tirtha Mandal、Velayutham Ravichandiran、Jyotirmayee Dash

  DOI：10.1039/d1gc03340a

  日期：——

  The cycloaddition of N-sulfonyl and N-sulfamoyl azides with terminal alkynes generally produces amide derivatives via ketenimine intermediates. We herein delineate a Cu(I) catalyzed method using a prolinamide ligand that selectively generates N-sulfonyl and sulfamoyltriazoles in aqueous media by inhibiting the cleavage of the N1–N2 bond of 5-cuprated triazole intermediates. The present method is mild

  N-磺酰基和N-氨磺酰基叠氮化物与末端炔烃的环加成通常通过烯酮亚胺中间体产生酰胺衍生物。我们在此描述了一种使用脯氨酰胺配体的Cu( I ) 催化方法，该方法通过抑制 5-铜三唑中间体的N 1 -N 2键的裂解，在水介质中选择性生成 N -磺酰基和氨磺酰三唑。本方法温和且耐空气、湿气和多种官能团，从而可以轻松获得各种三唑产品。
• [EN] 5-AMINOLEVULINATE SYNTHASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE 5-AMINOLÉVULINATE SYNTHASE ET LEURS MÉTHODES D'UTILISATION
  申请人：MANETSCH ROMAN

  公开号：WO2018237163A1

  公开（公告）日：2018-12-27

  Disclosed herein, are 5-Aminolevulinate synthase inhibitors and methods for their use in the treatment of porphyria. In at least one specific embodiment, the 5-Aminolevulinate synthase inhibitors can include compounds or salts thereof of Formulas (I-V).

  本文披露了5-氨基丙酮酸合成酶抑制剂及其在治疗porphyria中的使用方法。在至少一个具体实施例中，5-氨基丙酮酸合成酶抑制剂可以包括Formula（I-V）的化合物或其盐。
• Iridium-Catalyzed Direct C−H Amidation Polymerization: Step-Growth Polymerization by C−N Bond Formation via C−H Activation to Give Fluorescent Polysulfonamides
  作者：Yoon-Jung Jang、Soon-Hyeok Hwang、Tae-Lim Choi

  DOI：10.1002/anie.201707446

  日期：2017.11.13

  activation of C−H bonds to produce polysulfonamides by an atom‐economical and green method using iridium‐catalyzed direct C−H amidation polymerization (DCAP). After screening various directing groups, additives, silver salts, concentrations, and temperatures to optimize DCAP, high‐molecular‐weight (up to 149 kDa) and defect‐free polysulfonamides were synthesized from various bis‐sulfonyl azides. Although

  我们报告了一种通过铱原子催化的直接CHH酰胺化聚合（DCAP）的原子经济和绿色方法活化CH键以产生聚磺酰胺的有效策略。在筛选了各种导向基团，添加剂，银盐，浓度和温度以优化DCAP之后，由各种双磺酰叠氮化物合成了高分子量（最高149 kDa）和无缺陷的聚磺酰胺。尽管这些聚合物没有常规的荧光共轭核，但由于激发态的分子内质子转移过程，它们在光激发时会发出斯托克斯位移大且量子产率高的蓝光。
• 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.
• Diversity-Oriented Polymerization: One-Shot Synthesis of Library of Graft and Dendronized Polymers by Cu-Catalyzed Multicomponent Polymerization
  作者：Hyunseok Kim、Ki-Taek Bang、Inho Choi、Jin-Kyung Lee、Tae-Lim Choi

  DOI：10.1021/jacs.6b04695

  日期：2016.7.13

  Graft and dendronized polymers have attracted much attention in the polymer community, and there have been significant efforts to develop better synthetic methods. Herein, we report the highly efficient synthesis of graft and dendronized polymers by using Cu-catalyzed multicomponent polymerization (MCP). Based on diversity-oriented synthesis, we prepared a library of various graft and dendronized polymers from combinations of three types of monomers (mono-functionalized alkynes, bis-sulfonyl azides, and diamines/diols) that are bench stable and readily accessible. After reaction optimization, 54 samples of high-molecular-weight graft and dendronized polymers were prepared, the MCP method allowing simultaneous manipulation of the structures of both the main chains and the side chains. Moreover, because of the severe steric hindrance of the side chains, these polymers adopted extended conformations, as shown by the large shape parameter in solution. Also, the extended morphology of the single polymer chains was directly visualized by atomic force microscopy and transmission electron microscopy in the solid state. Most importantly, this diversity-oriented polymerization became possible because of highly step-economical and efficient one-step MCP, paving the way toward the easily tunable synthesis of graft and dendronized polymers.