N-(2-azidoethyl)benzamide | 72200-26-1

• 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: N-(2-azidoethyl)benzamide
• 英文别名: N-(2-Azidoethyl)benzamid；N-(β-Azido-aethyl)-benzamid；N-(2-Azido-aethyl)-benzamid
• CAS: 72200-26-1
• 化学式: C₉H₁₀N₄O
• 分子量: 190.205
• InChiKey: JCGANCYVCAOITN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-azidoethyl)benzamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 以95%的产率得到N-(2-氨基乙基)苯甲酰胺
  参考文献：
  名称：

  A Two-Step Continuous-Flow Synthesis of N-(2-Aminoethyl)acylamides through Ring-Opening/Hydrogenation of Oxazolines

  摘要：

  DOI：

  10.1002/chem.201102772
• 作为产物：
  描述：

  4,5-二氢-2-苯基恶唑 在 叠氮基三甲基硅烷 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以96%的产率得到N-(2-azidoethyl)benzamide
  参考文献：
  名称：

  A Two-Step Continuous-Flow Synthesis of N-(2-Aminoethyl)acylamides through Ring-Opening/Hydrogenation of Oxazolines

  摘要：

  DOI：

  10.1002/chem.201102772

文献信息

• The Development of a Versatile Trifunctional Scaffold for Biological Applications
  作者：Václav Vaněk、Jan Pícha、Benjamin Fabre、Miloš Buděšínský、Martin Lepšík、Jiří Jiráček

  DOI：10.1002/ejoc.201500255

  日期：2015.6

  We describe the synthesis of a trifunctional scaffold constructed from a planar core of trimesic acid derivatized with three propargylamine moieties. The scaffold was attached to a solid-phase resin through the carboxylic group of a fluorinated alkyl spacer arm. The orthogonal protection of two of the alkyne groups with triethylsilyl and triisopropylsilyl moieties enabled modular and efficient derivatization

  我们描述了由三个炔丙胺部分衍生的均苯三甲酸的平面核心构建的三功能支架的合成。支架通过氟化烷基间隔臂的羧基连接到固相树脂上。用三乙基甲硅烷基和三异丙基甲硅烷基部分对两个炔基进行正交保护，通过在两亲性 ChemMatrix 树脂上使用固相合成，可以模块化和有效地衍生出具有三种不同叠氮化物的支架。我们表明，氟标记可用于在从树脂上裂解后通过 19F NMR 光谱分析来量化含氟化合物的含量。
• High-throughput synthesis of azide libraries suitable for direct “click” chemistry and in situ screening
  作者：Rajavel Srinivasan、Lay Pheng Tan、Hao Wu、Peng-Yu Yang、Karunakaran A. Kalesh、Shao Q. Yao

  DOI：10.1039/b902338k

  日期：——

  building blocks (key components in click chemistry). We report herein a highly robust and efficient strategy for high-throughput synthesis of a 325-member azide library. The method is highlighted by its simplicity and product purity. The utility of the library is demonstrated with the subsequent “click” synthesis of the corresponding bidentate inhibitors against PTP1B.

  当前药物发现中的关键挑战是开发高通量（HT）合适的化学反应，该反应可快速合成酶抑制剂的各种化学文库。叠氮化物和炔烃之间的Cu（I）催化的1,3-偶极环加成反应，称为“点击化学”，是近年来受到最广泛关注的一种方法。尽管它广受欢迎，但仍然缺乏可靠而有效的化学策略，这些策略无法访问各种包含叠氮化物的结构单元（点击化学中的关键成分）的库。我们在这里报告了一个高健壮和高效的策略，可用于325个成员的叠氮化物文库的高通量合成。该方法以其简单性和产品纯度而著称。
• Reactions of trivalent phosphorus compounds with azides containing a mobile H-atom
  作者：Yu.G. Gololobov、N.I. Gusar'、M.P. Chaus

  DOI：10.1016/s0040-4020(01)96459-2

  日期：1985.1

  Investigation of the reactions of α-azidocarboxylic acids, N-(2-azidoethyl) amides and N-(2-azidoethyl) amines with trivalent P compounds shows that the intramolecular cyclization to spirophosphoranes of the intermediate phosphazo-compounds is typical of the azides of the first and third types but not of the second type. It is concluded that such cyclization is possible only where the functional group

  研究α-叠氮基羧酸，N-（2-叠氮基乙基）酰胺和N-（2-叠氮基乙基）胺与三价P化合物的反应表明，中间体磷酸偶氮化合物分子内环化为螺磷phosph烷是叠氮化物的典型叠氮化物第一种和第三种，但不是第二种。结论是，仅当起始叠氮化物的官能团包含足够移动的氢原子或高度亲核的含质子的基团时，这样的环化才是可能的。已经开发了生产咪唑啉和恶唑啉的新的通用方法。
• Indole–triazole conjugates are selective inhibitors and inducers of bacterial biofilms
  作者：Marine J. Minvielle、Cynthia A. Bunders、Christian Melander

  DOI：10.1039/c3md00064h

  日期：——

  Herein is described a method of accessing indole–triazole and benzothiophene–triazole analogues that selectively promote or inhibit biofilm formation by Gram-positive and Gram-negative bacteria. Structure/function studies revealed that the addition of a bromine atom at the 2-position of the indole–triazole scaffold altered activity against both Gram-negative and Gram-positive bacteria and could transform a biofilm inhibitor into a biofilm inducer. Isosteric replacement of the indole core by a benzothiophene significantly impaired anti-biofilm activity. A competition assay exposing Escherichia coli to the most potent biofilm inducer and an inhibitor of E. coli biofilm formation was performed. The inducer exhibited the ability to mute the effect of the anti-biofilm compound for this targeted bacterial population.

  本文介绍了一种获得吲哚三唑和苯并噻吩三唑类似物的方法，这些类似物可选择性地促进或抑制革兰氏阳性和革兰氏阴性细菌形成生物膜。结构/功能研究表明，在吲哚三唑支架的 2 位添加一个溴原子会改变对革兰氏阴性菌和革兰氏阳性菌的活性，并可将生物膜抑制剂转变为生物膜诱导剂。用苯并噻吩等位取代吲哚核心会显著降低抗生物膜活性。将大肠杆菌与最有效的生物膜诱导剂和大肠杆菌生物膜形成抑制剂进行了竞争试验。对于这一目标细菌群，诱导剂显示出了削弱抗生物膜化合物效果的能力。
• Interrogating Aptamer Chemical Space Through Modified Nucleotide Substitution Facilitated by Enzymatic DNA Synthesis
  作者：Germain Niogret、Alix Bouvier‐Müller、Chiara Figazzolo、Jack M. Joyce、Frédéric Bonhomme、Patrick England、Olena Mayboroda、Riccardo Pellarin、Gilles Gasser、James H. R. Tucker、Julian A. Tanner、G. Paul Savage、Marcel Hollenstein

  DOI：10.1002/cbic.202300539

  日期：2024.1.2

  Chemical modification of aptamers is an important step to improve their performance and stability in biological media. This can be performed either during their identification (mod‐SELEX) or after the in vitro selection process (post‐SELEX). In order to reduce the complexity and workload of the post‐SELEX modification of aptamers, we have evaluated the possibility of improving a previously reported, chemically modified aptamer by combining enzymatic synthesis and nucleotides bearing bioisosteres of the parent cubane side‐chains or substituted cubane moieties. This method lowers the synthetic burden often associated with post‐SELEX approaches and allowed to identify one additional sequence that maintains binding to the PvLDH target protein, albeit with reduced specificity. In addition, while bioisosteres often improve the potency of small molecule drugs, this does not extend to chemically modified aptamers. Overall, this versatile method can be applied for the post‐SELEX modification of other aptamers and functional nucleic acids.

  摘要对aptamers进行化学修饰是提高其在生物介质中的性能和稳定性的重要步骤。化学修饰既可以在识别过程中进行（mod-SELEX），也可以在体外筛选过程后进行（post-SELEX）。为了降低灵敏配体后 SELEX 修饰的复杂性和工作量，我们评估了通过结合酶法合成和带有母方烷侧链或取代方烷分子的生物异构体的核苷酸来改进之前报道的化学修饰灵敏配体的可能性。这种方法减轻了通常与后 SELEX 方法相关的合成负担，并能鉴定出一种额外的序列，它能保持与 PvLDH 目标蛋白的结合，尽管特异性有所降低。此外，虽然生物异构体通常能提高小分子药物的效力，但化学修饰的适配体却不能做到这一点。总之，这种多用途方法可用于其他适配体和功能核酸的 SELEX 后修饰。