8-ethynyl-2′-deoxyadenosine

• 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-ethynyl-2′-deoxyadenosine
• 英文别名: 2'-deoxy-8-ethynyladenosine；8-ethynyl-2'-deoxyadenosine；(2R,3S,5R)-5-(6-amino-8-ethynyl-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol；(2R,3S,5R)-5-(6-amino-8-ethynylpurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• 化学式: C₁₂H₁₃N₅O₃
• 分子量: 275.267
• InChiKey: VRKPVSVQAAYZAY-LKEWCRSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-ethynyl-2′-deoxyadenosine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以94%的产率得到2'-deoxy-8-ethyladenosine
  参考文献：
  名称：

  Synthesis and Antiviral Activities of 8-Alkynyl-, 8-Alkenyl-, and 8-Alkyl-2'-deoxyadenosine Analogs

  摘要：

  Palladium-catalyzed cross-coupling of 8-bromo-2'-deoxyadenosine with terminal alkynes in the presence of copper(I) iodide in dimethylformamide resulted in a series of 8-(1-alkyn-1-yl)-2'-deoxyadenosines. Hydrogenation of alkynyl derivatives over 10 % Pd/C under atmospheric pressure gave 8-n-alkyl analogues in nearly quantitative yields. On partial saturation of heptynyl, pentynyl, and propynyl derivatives over Lindlar catalyst, the corresponding cis-olefins were obtained along with minor amounts of trans isomers. Of the analogues tested, the following showed some activity, i.e. they were found to be active at concentrations that were at least 3-fold lower than the cytotoxic concentrations: the 8-heptynyl derivative against vaccinia virus (VV), vesicular stomatitis virus (VSV), cytomegalovirus (CMV), and respiratory syncytial virus (RSV); the 8-propyl derivative against varicella-zoster virus (VZV) and CMV; the 8-pentyl derivative against CMV; the 8-heptyl derivative against VV, CMV, RSV, and influenza A; slid the 8-heptenyl derivative against VV, RSV, and influenza A. The unsubstituted 2'-deoxyadenosine did not show any antiviral effect, except against RSV. Except for 8-propyl-dA, the antivirally active dA analogues were rather inhibitory to the growth of human embryonic lung cells. The most cytotoxic was the 8-ethynyl derivative.

  DOI：

  10.1021/jm00035a010
• 作为产物：
  描述：

  2'-脱氧腺苷 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 溴 、 sodium acetate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 8-ethynyl-2′-deoxyadenosine
  参考文献：
  名称：

  多种大小的方法可将高度荧光的非天然核苷酸掺入并延伸到DNA中。

  摘要：

  我们准备了一系列大小不一的非天然核苷酸，它们均基于荧光（dApyrTP，dUpyrTP，dUantTP，dUthiTP）和淬灭（dUazoTP）单元，以及具有小的官能团（dAethTP，dAoctTP，dUethTP，dUiodTP）的核苷酸。脱氧腺苷和脱氧尿苷，并检查了它们在酶促掺入和扩展到DNA中的适用性。我们观察到引物延伸过程中掺入和延伸能力的大小依赖性（遵循dUiodTP = dUethTP = dUthiTP> dUazoTP> dUpyrTP> dUantTP的顺序）。该结果得到圆二色性（CD）光谱的支持，圆二色性光谱揭示了不同B型DNA结构的趋势，该结构取决于脱氧尿苷5位单元的大小（dUiodTP> dUethTP> dUthiTP> dUpyrTP）。从PCR产物。有趣的是，dUthiTP可以在引物延伸甚至PCR扩增过程中掺入并延伸到长DNA链中，CD光谱证实了稳定的二级B

  DOI：

  10.1016/j.bmc.2017.03.045

文献信息

• Synthesis and in vitro cytotoxicity of deoxyadenosine–bile acid conjugates linked with 1,2,3-triazole
  作者：Daniela Perrone、Olga Bortolini、Marco Fogagnolo、Elena Marchesi、Lara Mari、Chiara Massarenti、Maria Luisa Navacchia、Fabio Sforza、Katia Varani、Massimo Luigi Capobianco

  DOI：10.1039/c3nj00513e

  日期：——

  report herein the synthesis and biological evaluation of novel deoxynucleoside–bile acid conjugates linked through a 1,2,3-triazole ring. The conjugates were synthesized via Cu(I) mediated 1,3-dipolar cycloaddition reaction (‘click’ chemistry) of 3-azidobile acid derivatives and terminal alkyne moieties linked to the C-8 position of deoxyadenosine. All novel molecules were evaluated in vitro for their

  我们在这里报告了通过1,2,3-三唑环连接的新型脱氧核苷-胆汁酸缀合物的合成和生物学评估。通过Cu（I）介导的3-叠氮胆酸衍生物和与脱氧腺苷的C-8位相连的末端炔基部分的1，3-偶极环加成反应（“点击”化学）合成了缀合物。在体外评估了所有新分子对四种人类细胞系（即白血病T Jurkat和K562；结肠癌HCT116；和卵巢癌A2780）的抗增殖活性以及对人成纤维细胞的细胞毒性。几种缀合物显示出对人白血病T细胞的强抗增殖活性。观察到最佳的细胞毒性两种白血病细胞系上的HdA-CDC的IC 50最高为8.51μM。还确定了几种缀合物的凋亡活性。
• [EN] BORANE DERIVATES OF ADENOSINE<br/>[FR] DÉRIVÉS BORANES DE L'ADÉNOSINE
  申请人：INST BIOLOG MEDYCZNEJ POLSKIEJ

  公开号：WO2010090541A1

  公开（公告）日：2010-08-12

  A purine nucleoside derivative comprising a boron cluster or its complex with a metal (metallocarborane) conjugated to at least one of: a nucleic base, sugar residue or sugar residue analogue.

  一种含硼簇或其与金属形成的复合物（金属卡烷）的嘌呤核苷衍生物，与至少一种核苷酸碱基、糖残基或糖残基类似物共轭。
• Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an <i>N</i>-Unsubstituted 1,2,3-Triazol-4-yl Moiety
  作者：Zhiwei Wen、Paloma R. Tuttle、A. Hasan Howlader、Anna Vasilyeva、Laura Gonzalez、Antonija Tangar、Ruipeng Lei、Eduardo E. Laverde、Yuan Liu、Jaroslava Miksovska、Stanislaw F. Wnuk

  DOI：10.1021/acs.joc.8b03135

  日期：2019.3.15

  The Cu(I)- or Ag(I)-catalyzed cycloaddition between 8-ethynyladenine or guanine nucleosides and TMSN 3 gave 8-(1-H-1,2,3-triazol-4-yl) nucleosides in good yields. On the other hand, reactions of 5-ethynyluracil or cytosine nucleosides with TMSN3 led to the chemoselective formation of triazoles via Cu(I)-catalyzed cycloaddition or vinyl azides via Ag(I)-catalyzed hydroazidation. These nucleosides with a minimalistic triazolyl modification showed excellent fluorescent properties with 8-(1-H-1,2,3-triazol-4-yl)-2'-deoxyadenosine (8-TrzdA), exhibiting a quantum yield of 44%. The 8-TrzdA 5'-triphosphate was incorporated into duplex DNA containing a one-nucleotide gap by DNA polymerase beta.
• Naphthalene-based environmentally sensitive fluorescent 8-substituted 2′-deoxyadenosines: Application to DNA detection
  作者：Azusa Suzuki、Naoya Takahashi、Yuji Okada、Isao Saito、Nobukatsu Nemoto、Yoshio Saito

  DOI：10.1016/j.bmcl.2012.11.029

  日期：2013.2

  We synthesized various C8-naphthylethynylated 2'-deoxyadenosine derivatives and investigated their photophysical properties. Among them, cyano- and N,N-dimethylamino-substituted 8-naphthylethynylated 2'-deoxyadenosine derivatives ((cn)A and (dn)A) showed strong fluorescence with high quantum yields and a remarkable solvatofuorochromicity. In particular, fluorescence of N,N-dimethylamino-substituted (2,6dn)A was not quenched by neighboring guanines (Gs) when incorporated in DNA duplexes, in contrast to (cn)A. We developed a new fluorescent probe containing (2,6dn)A that can be used for the detection of target DNA via a bulge formation regardless of the neighboring sequences. (c) 2012 Elsevier Ltd. All rights reserved.