8-(phenylethynyl)-Adenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-(phenylethynyl)-Adenosine
• 英文别名: 8-(2-phenylethyn-1-yl)adenosine；8-(2-phenylethynyl)adenosine；8-(Phenylethynyl)adenosine；8-(phenylethynyl)denosine；8-Phenylethynyladenosine；(2R,3R,4S,5R)-2-[6-amino-8-(2-phenylethynyl)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• 化学式: C₁₈H₁₇N₅O₄
• 分子量: 367.364
• InChiKey: ZYEXHNHGCDESIU-XKLVTHTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-(phenylethynyl)-Adenosine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以97%的产率得到8-(2-phenylethyl)adenosine
  参考文献：
  名称：

  腺苷衍生物作为 A1、A2A、A2B 和 A3 腺苷受体配体的合成和评价，其中含有硼簇作为苯基等排体和选择性 A3 激动剂

  摘要：

  合成了一系列腺苷和 2'-脱氧腺苷对，用 1,12-二碳-氯-十二硼烷簇或在相同位置用苯基修饰，并在 A 1、A 2A、A 2B处测定它们的亲和力和 A 3腺苷受体 (ARs)。虽然注意到 AR 亲和力差异，但对于大多数测试的配体，观察到优先结合 A 3 AR 而不是其他 AR 的一般趋势。具体而言，5'-乙基氨基甲酰基-N 6 -(3-苯基丙基)腺苷( 18 )、N 6 -(3-苯基丙基)-2-氯腺苷( 24 )和N 6-(3-苯基丙基)腺苷( 40 )显示出纳摩尔A 3亲和力(K i分别为4.5、6.4和7.5 nM)。在含硼簇的化合物中，最高的 A 3亲和力（K i 206 nM）是对C2 修饰的腺苷衍生物41 。在匹配的分子对中，发现带有硼簇的类似物对腺苷受体的结合亲和力低于相应的苯基类似物。然而，有趣的是，几个硼簇修饰的腺苷配体显示出比相应的苯基类似物显着更高的 A 3受体选择性：

  DOI：

  10.1016/j.ejmech.2021.113607
• 作为产物：
  描述：

  苯乙炔 、 8-溴膘苷 在 copper(l) iodide 、 palladium diacetate 、 三乙胺 、 tris(4,6-dimethyl-3-sulfonatophenyl)phosphine trisodium salt hydrate 作用下， 以 水 、 乙腈 为溶剂， 以53.1%的产率得到8-(phenylethynyl)-Adenosine
  参考文献：
  名称：

  使用水溶性钯催化剂在水性溶剂中高效 Sonogashira 偶联未受保护的卤代核苷

  摘要：

  C-炔基化核苷的各种应用促进了其制备的有效合成方法的持续发展。我们报告了一种有效且对环境无害的 Sonogashira 偶联反应，用于在水性溶剂中对未受保护的卤代核苷进行炔基化。Pd(OAc)2、CuI 和 TXPTS [三(2,4-二甲基-5-磺基苯基)膦三钠] 的组合为 H2O/CH3CN 中 8-溴嘌呤和 5-碘尿苷的炔基化提供了有效的催化剂 (1 :1) 产率范围为 42 至 98 %。

  DOI：

  10.1002/ejoc.201000313

文献信息

• Efficient Sonogashira Coupling of Unprotected Halonucleosides in Aqueous Solvents Using Water-Soluble Palladium Catalysts
  作者：Joon Hyung Cho、Caitlin D. Prickett、Kevin H. Shaughnessy

  DOI：10.1002/ejoc.201000313

  日期：2010.7

  prompted the continuing development of efficient synthetic methods for their preparation. We report an efficient andenvironmentally benign Sonogashira coupling reaction for alkynylation of unprotected halonucleosides in an aqueous solvent. The combination of Pd(OAc)2, CuI, and TXPTS [trisodium tri(2,4-dimethyl-5-sulfonatophenyl)phosphane] provided an effective catalyst for the alkynylation of 8-bromopurines

  C-炔基化核苷的各种应用促进了其制备的有效合成方法的持续发展。我们报告了一种有效且对环境无害的 Sonogashira 偶联反应，用于在水性溶剂中对未受保护的卤代核苷进行炔基化。Pd(OAc)2、CuI 和 TXPTS [三(2,4-二甲基-5-磺基苯基)膦三钠] 的组合为 H2O/CH3CN 中 8-溴嘌呤和 5-碘尿苷的炔基化提供了有效的催化剂 (1 :1) 产率范围为 42 至 98 %。
• Bicyclic Compounds and Their Use
  申请人：Fairlamb Ian

  公开号：US20090299049A1

  公开（公告）日：2009-12-03

  The present invention provides fluorescent bicyclic compounds of the formula (I); wherein ring A, the broken lines -----, C 1 ----C 2 , R 4 and R 1 are as defined herein. The invention also relates to nucleoside and nucleotide analogues of said compounds, and their use as biological markers.

  本发明提供了式(I)的荧光双环化合物，其中环A，断裂的线-----，C1----C2，R4和R1如本文所定义。本发明还涉及该化合物的核苷和核苷酸类似物，以及它们作为生物标记物的用途。
• Purine and deazapurine nucleosides: synthetic approaches, molecular modelling and biological activity
  作者：Gloria Cristalli、Stefano Costanzi、Catia Lambertucci、Sara Taffi、Sauro Vittori、Rosaria Volpini

  DOI：10.1016/s0014-827x(03)00019-3

  日期：2003.3

  A number of ligands for the adenosine binding sites has been obtained by using nucleoside convergent and divergent synthesis. Most of our nucleosides have been synthesized by coupling 2,6-dichloropurine (1), 2,6-dichloro-1-deazapurine (2), 2,6-dichloro-3-deazapurine (3) with ribose, 2- and 3-deoxyribose and 2,3-dideoxyribose derivatives. The use of these versatile synthons allowed the introduction of various substituents in 2- and/or 6-positions. The glycosylation site and the anomeric configuration of the obtained nucleosides were assigned on the basis of spectroscopic studies and confirmed by molecular models. A series of potent adenosine receptor ligands has been obtained by using divergent approaches, mostly starting from guanosine. Substitutions in 2, 6, 8, and 5' position of adenosine molecule led to ligands selective for the different adenosine receptor subtypes. Furthermore, we investigated the molecular bases of the different behavior of 2- and 8-alkynyl adenosines, by means of NMR experiments and molecular modeling studies. With docking experiments, we demonstrated that the two class of molecules should have different binding modes that explain their different degree of affinity and the shift of their activity from agonistic (2-substituted derivatives) to antagonistic (8-substituted derivatives).
• Sonogashira alkynylation of unprotected 8-brominated adenosines and guanosines: fluorescence properties of compact conjugated acetylenes containing a purine ring
  作者：Andrew G. Firth、Ian J.S. Fairlamb、Kate Darley、Christoph G. Baumann

  DOI：10.1016/j.tetlet.2006.03.100

  日期：2006.5

  A practical Sonogashira alkynylation protocol for the preparation of 8-alkynylated adenosines and guanosines has been developed. Protection of the sugar hydroxyl substituents is not required; protection hinders the purification of these products. A preliminary fluorescent study is reported, which shows that the presence of a substituent on the phenylene ring influences the fluorescent properties considerably, an outcome that could be utilized in biological applications. (c) 2006 Elsevier Ltd. All rights reserved.
• SYNTHESIS AND ADENOSINE RECEPTOR AFFINITY AND POTENCY OF 8-ALKYNYL DERIVATIVES OF ADENOSINE
  作者：C. Lambertucci、S. Costanzi、S. Vittori、R. Volpini、G. Cristalli

  DOI：10.1081/ncn-100002509

  日期：2001.3.31

  Adenosine derivatives bearing different (ar)alkynyl chains at the 8-position were synthesized and tested at human adenosine receptors. Binding studies showed that all compounds possess affinity for the A(3) subtype in the high nM range. Moreover, guanosine 5'-O-(3-[S-35]thio)triphosphate binding assay indicated that the 8-alkynyl adenosines behaved as antagonists of NECA at A(3) receptors.