2-(1H-pyrazol-1-yl)-6-((trimethylsilyl)ethynyl)pyridine | 1312592-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(1H-pyrazol-1-yl)-6-((trimethylsilyl)ethynyl)pyridine
• 英文别名: 2-(1H-pyrazol-1-yl)-6-[2-(trimethylsilyl)ethynyl]-pyridine；2-(1H-pyrazol-1-yl)-6-[2-(trimethylsilyl)ethynyl]pyridine
• CAS: 1312592-21-4
• 化学式: C₁₃H₁₅N₃Si
• 分子量: 241.368
• InChiKey: GVCOARSCTXOSMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  30.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(1H-pyrazol-1-yl)-6-((trimethylsilyl)ethynyl)pyridine 在 四丁基氟化铵 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 0.25h， 生成 1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-(2-(1H-pyrazol-1-yl)-6-pyridyl)-1,2,3-triazole
  参考文献：
  名称：

  Design and synthesis of O-GlcNAcase inhibitors via ‘click chemistry’ and biological evaluations

  摘要：

  Protein O-GlcNAcylation has been shown to play an important role in a number of biological processes, including regulation of the cell cycle, DNA transcription and translation, signal transduction, and protein degradation. O-GlcNAcase (OGA) is responsible for the removal of O-linked beta-N-acetylglucosamine (O-GlcNAc) from serine or threonine residues, and thus plays a key role in O-GlcNAc metabolism. Potent OGA inhibitors are useful tools for studying the cellular processes of O-GlcNAc, and may be developed as drugs for the treatment neurodegenerative diseases. In this study, Cu(I)-catalyzed 'Click' cycloaddition reactions between glycosyl azides and alkynes were exploited to generate inhibitory candidates of OGA. Enzymatic kinetic screening revealed that compound 7 was a potent competitive inhibitor of human O-GlcNAcase (K(i) = 185.6 mu M). Molecular docking simulations of compound 7 into CpOGA (Clostridium perfringens OGA) suggested that strong pi-pi stacking interaction between the compound and W490 considerably contributed to improving the inhibitory activity. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.026
• 作为产物：
  描述：

  2-溴-6-(1H-吡唑-1-基)吡啶 、 三甲基乙炔基硅 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以87%的产率得到2-(1H-pyrazol-1-yl)-6-((trimethylsilyl)ethynyl)pyridine
  参考文献：
  名称：

  Design and synthesis of O-GlcNAcase inhibitors via ‘click chemistry’ and biological evaluations

  摘要：

  Protein O-GlcNAcylation has been shown to play an important role in a number of biological processes, including regulation of the cell cycle, DNA transcription and translation, signal transduction, and protein degradation. O-GlcNAcase (OGA) is responsible for the removal of O-linked beta-N-acetylglucosamine (O-GlcNAc) from serine or threonine residues, and thus plays a key role in O-GlcNAc metabolism. Potent OGA inhibitors are useful tools for studying the cellular processes of O-GlcNAc, and may be developed as drugs for the treatment neurodegenerative diseases. In this study, Cu(I)-catalyzed 'Click' cycloaddition reactions between glycosyl azides and alkynes were exploited to generate inhibitory candidates of OGA. Enzymatic kinetic screening revealed that compound 7 was a potent competitive inhibitor of human O-GlcNAcase (K(i) = 185.6 mu M). Molecular docking simulations of compound 7 into CpOGA (Clostridium perfringens OGA) suggested that strong pi-pi stacking interaction between the compound and W490 considerably contributed to improving the inhibitory activity. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.026

文献信息

• Discrete Self‐Assembled Metallo‐Foldamers with Heteroleptic Sequence Specificity
  作者：Dan Preston

  DOI：10.1002/anie.202108456

  日期：2021.9

  Discrete and structurally diverse foldamer sequences are constructed in both natural and abiotic systems primarily using inert connectivity with irreversible organic covalent bonds, serving to preserve the identity of the sequence. The formation of sequences under thermodynamic control using labile coordination bonds would be attractive for synthetic ease and modular capability, but this presents issues

  在天然和非生物系统中构建离散且结构多样的折叠体序列，主要使用惰性连接与不可逆的有机共价键，用于保持序列的身份。使用不稳定的配位键在热力学控制下形成序列对于合成的简易性和模块化能力来说很有吸引力，但这会带来有关序列保存的问题。这里介绍了一种将钯 (II) 金属离子整合到序列本身中的方法，通过在金属中心使用配体排列的互补配对来保持保真度。这是通过使用不同齿数和/或氢键能力的位点来实现的。以这种方式，离散和有序的金属序列在一步中形成为热力学产物，
• A symmetry interaction approach to [M₂L₂]⁴⁺ metallocycles and their self-catenation
  作者：Dan Preston、Amanda R. Inglis、Anna L. Garden、Paul E. Kruger

  DOI：10.1039/c9cc07130j

  日期：——

  A symmetry interaction approach to [M₂L₂]⁴⁺ metallocycles and their self-catenanes.

  一种对[M₂L₂]⁴⁺金属环及其自我串联体的对称交互作用方法。
• A Catalogue of Orthogonal Complementary Ligand Pairings for Palladium(II) Complexes
  作者：Jason S. Buchanan、Dan Preston

  DOI：10.1002/asia.202200272

  日期：2022.6

  A catalogue of bis-ligand Pd(II) complexes has been developed. Each pair of ligands exhibits complementary to each other through denticity (2 : 2 or 3 : 1) and hydrogen bonding donor/acceptor capability. High levels of orthogonality between these pairings were demonstrated, with pair-based sorting observed.

  双配体 Pd(II) 配合物的目录已经开发出来。每对配体通过齿数（2:2 或 3:1）和氢键供体/受体能力表现出彼此互补。证明了这些配对之间的高水平正交性，并观察到了基于配对的排序。
• A Lantern‐Shaped Pd(II) Cage Constructed from Four Different Low‐Symmetry Ligands with Positional and Orientational Control: An Ancillary Pairings Approach
  作者：Dan Preston、Jack D. Evans

  DOI：10.1002/anie.202314378

  日期：2023.12.4

  One of the key challenges of metallo‐supramolecular chemistry is to maintain the ease of self‐assembly but, at the same time, create structures of increasingly high levels of complexity. In palladium(II) quadruply stranded lantern‐shaped cages, this has been achieved through either 1) the formation of heteroleptic (multi‐ligand) assemblies, or 2) homoleptic assemblies from low‐symmetry ligands. Heteroleptic cages formed from low‐symmetry ligands, a hybid of these two approaches, would add an additional rich level of complexity but no examples of these have been reported. Here we use a system of ancillary complementary ligand pairings at the termini of cage ligands to target heteroleptic assemblies: these complementary pairs can only interact (through coordination to a single Pd(II) metal ion) between ligands in a cis position on the cage. Complementarity between each pair (and orthogonality to other pairs) is controlled by denticity (tridentate to monodentate or bidentate to bidentate) and/or hydrogen‐bonding capability (AA to DD or AD to DA). This allows positional and orientational control over ligands with different ancillary sites. By using this approach, we have successfully used low‐symmetry ligands to synthesise complex heteroleptic cages, including an example with four different low‐symmetry ligands.

  摘要 金属超分子化学面临的主要挑战之一是保持自组装的简易性，同时创造出复杂程度越来越高的结构。在钯(II)四股灯笼形笼子中，实现这一目标的方法是：1）形成异配体（多配体）组装体；或 2）由低对称性配体形成同配体组装体。由低对称性配体形成的异极笼是这两种方法的混合体，将增加额外的复杂性，但目前还没有这方面的实例报道。在这里，我们利用笼状配体末端的辅助互补配体配对系统来实现异方性组装：这些互补配对只能在笼状配体上处于顺式位置的配体之间相互作用（通过与单个钯（II）金属离子配位）。每对配体之间的互补性（以及与其他配体之间的正交性）受齿性（三叉齿性与单齿性或双齿性与双齿性）和/或氢键能力（AA 与 DD 或 AD 与 DA）的控制。这样就可以对具有不同辅助位点的配体进行位置和方向控制。通过使用这种方法，我们成功地利用低对称性配体合成了复杂的异性笼，包括一个含有四种不同低对称性配体的例子。