(5-azidopent-1-ynyl)trimethylsilane | 1233978-12-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (5-azidopent-1-ynyl)trimethylsilane
• 英文别名: (5-azidopent-1-yn-1-yl)trimethylsilane；5-Azidopent-1-ynyl(trimethyl)silane；5-azidopent-1-ynyl(trimethyl)silane
• CAS: 1233978-12-5
• 化学式: C₈H₁₅N₃Si
• 分子量: 181.313
• InChiKey: DYFVLSJIMWROLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5-azidopent-1-ynyl)trimethylsilane 在 copper(ll) sulfate pentahydrate 、 四丁基氟化铵 、 水 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 sodium ascorbate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 6.58h， 生成 (1R,3R,4R,5S)-N-(3-{1-[3-(5-acetamido-1H-indol-1-yl)propyl]-1H-1,2,3-triazol-4-yl}propyl)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methylcyclohexanecarboxamide
  参考文献：
  名称：

  Nanomolar E-Selectin Antagonists with Prolonged Half-Lives by a Fragment-Based Approach

  摘要：

  Selectins, a family of C-type lectins, play a key role in inflammatory diseases (e.g., asthma and arthritis). However, the only millimolar affinity of sialyl Lewis(x) (sLe(x)), which is the common tetrasaccharide epitope of all physiological selectin ligands, has been a major obstacle to the development of selectin antagonists for therapeutic applications. In a fragment-based approach guided by NMR, ligands binding to a second site in close proximity to a sLe(x) mimic were identified. A library of antagonists obtained by connecting the sLe(x) mimic to the best second-site ligand via triazole linkers of different lengths was evaluated by surface plasmon resonance. Detailed analysis of the five most promising candidates revealed antagonists with K-D values ranging from 30 to 89 nM. In contrast to carbohydratelectin complexes with typical half-lives (t(1/2)) in the range of one second or even less, these fragment-based selectin antagonists show t(1/2) of several minutes. They exhibit a promising starting point for the development of novel anti-inflammatory drugs.

  DOI：

  10.1021/ja4029582
• 作为产物：
  描述：

  5-(三甲基硅烷基)-4-戊炔-1-醇 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (5-azidopent-1-ynyl)trimethylsilane
  参考文献：
  名称：

  Nanomolar E-Selectin Antagonists with Prolonged Half-Lives by a Fragment-Based Approach

  摘要：

  Selectins, a family of C-type lectins, play a key role in inflammatory diseases (e.g., asthma and arthritis). However, the only millimolar affinity of sialyl Lewis(x) (sLe(x)), which is the common tetrasaccharide epitope of all physiological selectin ligands, has been a major obstacle to the development of selectin antagonists for therapeutic applications. In a fragment-based approach guided by NMR, ligands binding to a second site in close proximity to a sLe(x) mimic were identified. A library of antagonists obtained by connecting the sLe(x) mimic to the best second-site ligand via triazole linkers of different lengths was evaluated by surface plasmon resonance. Detailed analysis of the five most promising candidates revealed antagonists with K-D values ranging from 30 to 89 nM. In contrast to carbohydratelectin complexes with typical half-lives (t(1/2)) in the range of one second or even less, these fragment-based selectin antagonists show t(1/2) of several minutes. They exhibit a promising starting point for the development of novel anti-inflammatory drugs.

  DOI：

  10.1021/ja4029582

文献信息

• Novel Phosphinite and Phosphonite Copper(I) Complexes: Efficient Catalysts for Click Azide–Alkyne Cycloaddition Reactions
  作者：Steven Lal、Jayne McNally、Andrew J. P. White、Silvia Dı́ez-González

  DOI：10.1021/om200791u

  日期：2011.11.28

  The preparation of novel phosphinite- and phosphonite-bearing copper(I) complexes of the general formula [CuX(L)] is reported. These compounds, which remain scarce in the literature, could be prepared using readily available starting materials and were spectroscopically and structurally characterized. These complexes, together with their known phosphine and phosphite analogues, were then applied to

  报道了通式[CuX（L）]的新型次膦酸酯和亚膦酸酯的含铜（I）配合物的制备。这些化合物在文献中仍然很少，可以使用容易获得的起始原料制备，并在光谱和结构上进行表征。然后将这些配合物及其已知的膦和亚磷酸酯类似物一起用于叠氮化物和炔烃的1,3-偶极环加成反应，以发现新的配合物表现出最佳的活性。完全优化反应条件导致了一个值得注意的Click催化系统，该催化系统在非常温和的反应条件下，没有任何添加剂且使用低金属负载的情况下具有活性。
• Click Chemistry Approach to New N-Substituted Aminocyclitols as Potential Pharmacological Chaperones for Gaucher Disease
  作者：Lucía Díaz、Jordi Bujons、Josefina Casas、Amadeu Llebaria、Antonio Delgado

  DOI：10.1021/jm100198t

  日期：2010.7.22

  New N-alkylaminocyclitols bearing a 1,2,3-triazole system at different positions of the alkyl chain have been prepared as potential GCase pharmacological chaperones using click chemistry approaches. Among them, compounds 1d and 1e, with the shorter spacer (n = 1) between the alkyltriazolyl system and the aminocyclitol core, were the most active ones as GCase inhibitors, revealing a determinant effect

  已经使用点击化学方法制备了在烷基链的不同位置带有1,2,3-三唑系统的新的N-烷基氨基环醇，作为潜在的GCase药理伴侣。其中，化合物1d和1e具有较短的间隔基（n= 1）在烷基三唑基系统和氨基环糖醇核心之间，是最活跃的GCase抑制剂，显示了三唑环位置对活性的决定性作用。此外，SAR数据和计算对接模型表明了亲脂性和酶抑制之间的相关性，并提出了化合物的“扩展”和“弯曲”潜在结合模式。在“弯曲”模式下，活性最高的化合物可以在三唑部分和酶残基Q284之间建立氢键相互作用。在三唑和氨基环糖醇核心之间具有更长间隔基的化合物中，将排除这种相互作用。
• [EN] E-SELECTIN ANTAGONISTS<br/>[FR] ANTAGONISTES DE L'E-SÉLECTINE
  申请人：GLYCOMIMETICS INC

  公开号：WO2012037034A1

  公开（公告）日：2012-03-22

  Compounds, compositions and methods are provided for inhibiting in vitro and in vivo processes mediated by E-selectin binding. More specifically, particular glycomimetic compounds are described, wherein the compounds are E- selectin antagonists.

  提供了抑制E-选择素结合介导的体内外过程的化合物、组合物和方法。更具体地，描述了特定的糖类拟态化合物，其中这些化合物是E-选择素拮抗剂。
• Copper(I)-Phosphinite Complexes in Click Cycloadditions: Three-Component Reactions and Preparation of 5-Iodotriazoles
  作者：Juana M. Pérez、Peter Crosbie、Steven Lal、Silvia Díez-González

  DOI：10.1002/cctc.201600234

  日期：2016.7.6

  displayed by copper(I)–phosphinite complexes of general formula [CuBr(L)] in two challenging cycloadditions is reported: a) the one‐pot azidonation/cycloaddition of boronic acids, NaN3, and terminal alkynes; b) the cycloaddition of azides and iodoalkynes. These air‐stable catalysts led to very good results in both cases and the expected triazoles could be isolated in pure form under ‘Click‐suitable’ conditions

  据报道，通式[CuBr（L）]的铜（I）-亚膦酸酯络合物在两个具有挑战性的环加成反应中显示出显着的活性：a）硼酸，NaN 3和末端炔的单锅叠氮/环加成反应；b）叠氮化物和碘炔的环加成。这些空气稳定的催化剂在两种情况下均能获得很好的结果，并且可以在“适合点击”的条件下以纯净形式分离出预期的三唑。
• Synthesis and evaluation of radioiodinated estrogens for diagnosis and therapy of male urogenital tumours
  作者：Feodor Braun、Marcel Jaschinski、Philipp Täger、Verena Marmann、Melanie von Brandenstein、Barbara Köditz、Thomas Fischer、Sergio Muñoz-Vázquez、Beate Zimmermanns、Markus Dietlein、Ferdinand Sudbrock、Phillip Krapf、Dietmar Fischer、Axel Heidenreich、Alexander Drzezga、Stefan Kirsch、Markus Pietsch、Klaus Schomäcker

  DOI：10.1039/d3ob00114h

  日期：——

  We identified a new estrogen receptor (ER)-targeting ligand with picomolar affinity serving as vehicle for radioiodines. This ligand is a potential radiotheranostics for ER⁺ male tumours.

  我们发现了一种新的雌激素受体（ER）靶向配体，它具有皮摩尔亲和力，可作为放射性碘的载体。这种配体是治疗ER+男性肿瘤的潜在放射治疗药物。