(2R,3S,5R)-5-[6-amino-8-(2-trimethylsilylethynyl)purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol | 1053253-21-6

• 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: (2R,3S,5R)-5-[6-amino-8-(2-trimethylsilylethynyl)purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 1053253-21-6
• 化学式: C₁₅H₂₁N₅O₃Si
• 分子量: 347.449
• InChiKey: XJYSGWTZRSEDRU-HOSYDEDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.28
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (2R,3S,5R)-5-[6-amino-8-(2-trimethylsilylethynyl)purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol 在 palladium on activated charcoal ammonium hydroxide 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 1.75h， 生成 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：

  8-溴-2'-脱氧腺苷 、 三甲基乙炔基硅 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到(2R,3S,5R)-5-[6-amino-8-(2-trimethylsilylethynyl)purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
  参考文献：
  名称：

  DNA中新型荧光腺嘌呤类似物的光物理和碱基模拟特性的表征

  摘要：

  为了增加具有改善的性质的荧光碱基类似物的多样性，我们在这里提出了一种新的荧光腺嘌呤类似物三唑腺嘌呤（A的简单的基于点击化学合成Ť）及其光物理内DNA表征。甲Ť示出有前途的性能相比，广泛使用的腺嘌呤类似物2-氨基嘌呤。单链和双链 DNA 的量子产率分别达到 >20% 和 >5%，并且显示出对相邻碱基的依赖性。此外，A T仅显示 DNA 双链体的轻微不稳定，与 2-氨基嘌呤相当，并且圆二色性研究表明 A T仅对正常 B-DNA 造成最小的结构扰动。此外，我们发现 A T显示出与胸腺嘧啶良好的碱基配对特性，更令人惊讶的是，它与正常腺嘌呤也显示出良好的碱基配对特性。总之，A T作为一种新的荧光腺嘌呤类似物显示出强大的潜力，用于监测 DNA 微环境内的变化。

  DOI：

  10.1093/nar/gkr010

文献信息

• Characterization of photophysical and base-mimicking properties of a novel fluorescent adenine analogue in DNA
  作者：Anke Dierckx、Peter Dinér、Afaf H. El-Sagheer、Joshi Dhruval Kumar、Tom Brown、Morten Grøtli、L. Marcus Wilhelmsson

  DOI：10.1093/nar/gkr010

  日期：2011.5

  diversity of fluorescent base analogues with improved properties, we here present the straightforward click-chemistry-based synthesis of a novel fluorescent adenine-analogue triazole adenine (AT) and its photophysical characterization inside DNA. AT shows promising properties compared to the widely used adenine analogue 2-aminopurine. Quantum yields reach >20% and >5% in single- and double-stranded DNA, respectively

  为了增加具有改善的性质的荧光碱基类似物的多样性，我们在这里提出了一种新的荧光腺嘌呤类似物三唑腺嘌呤（A的简单的基于点击化学合成Ť）及其光物理内DNA表征。甲Ť示出有前途的性能相比，广泛使用的腺嘌呤类似物2-氨基嘌呤。单链和双链 DNA 的量子产率分别达到 >20% 和 >5%，并且显示出对相邻碱基的依赖性。此外，A T仅显示 DNA 双链体的轻微不稳定，与 2-氨基嘌呤相当，并且圆二色性研究表明 A T仅对正常 B-DNA 造成最小的结构扰动。此外，我们发现 A T显示出与胸腺嘧啶良好的碱基配对特性，更令人惊讶的是，它与正常腺嘌呤也显示出良好的碱基配对特性。总之，A T作为一种新的荧光腺嘌呤类似物显示出强大的潜力，用于监测 DNA 微环境内的变化。
• Synthesis and Antiviral Activities of 8-Alkynyl-, 8-Alkenyl-, and 8-Alkyl-2'-deoxyadenosine Analogs
  作者：Gyula Sagi、Laszlo Otvos、Satoru Ikeda、Graciela Andrei、Robert Snoeck、Erik De Clercq

  DOI：10.1021/jm00035a010

  日期：1994.4

  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.