2'-deoxy-8-(propyn-1-yl)adenosine | 156683-73-7

• 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: 2'-deoxy-8-(propyn-1-yl)adenosine
• 英文别名: (2R,3S,5R)-5-(6-amino-8-prop-1-ynylpurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 156683-73-7
• 化学式: C₁₃H₁₅N₅O₃
• 分子量: 289.294
• InChiKey: JJADQMVWPKZGHX-QXFUBDJGSA-N

物化性质

• 沸点：
  643.6±65.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  2'-deoxy-8-(propyn-1-yl)adenosine 在 吡啶 作用下， 反应 2.5h， 生成
  参考文献：
  名称：

  含2'-脱氧-8-（丙炔-1-基）腺苷的寡核苷酸：对双链体和四链体结构稳定性的影响。

  摘要：

  2'-Deoxy-8-（propyn-1-yl）adenosine已掺入合成的寡脱氧核糖核苷酸中，并通过UV，CD和1H NMR研究了其对双链和四链结构热稳定性的影响。获得的结果似乎表明修饰的碱基的存在对双链DNA的稳定性有负面影响，而显着增加了平行四链体结构的稳定性。

  DOI：

  10.1016/s0960-894x(00)00381-4
• 作为产物：
  描述：

  2'-脱氧腺苷 在 copper(l) iodide 、 四(三苯基膦)钯 、 溴 、 sodium acetate 、 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2'-deoxy-8-(propyn-1-yl)adenosine
  参考文献：
  名称：

  含2'-脱氧-8-（丙炔-1-基）腺苷的寡核苷酸：对双链体和四链体结构稳定性的影响。

  摘要：

  2'-Deoxy-8-（propyn-1-yl）adenosine已掺入合成的寡脱氧核糖核苷酸中，并通过UV，CD和1H NMR研究了其对双链和四链结构热稳定性的影响。获得的结果似乎表明修饰的碱基的存在对双链DNA的稳定性有负面影响，而显着增加了平行四链体结构的稳定性。

  DOI：

  10.1016/s0960-894x(00)00381-4

文献信息

• 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.
• 2′-deoxy-8-(propyn-1-yl)adenosine-containing oligonucleotides: effects on stability of duplex and quadruplex structures
  作者：Bruno Catalanotti、Aldo Galeone、Luigi Gomez-Paloma、Luciano Mayol、Antonietta Pepe

  DOI：10.1016/s0960-894x(00)00381-4

  日期：2000.9

  2'-Deoxy-8-(propyn-1-yl)adenosine has been incorporated in synthetic oligodeoxyribonucleotides and its influence on thermal stability of duplex and quadruplex structures investigated by UV, CD and 1H NMR. The obtained results seem to indicate that the presence of the modified base negatively affects the stability of double stranded DNA whereas remarkably increases the stability of parallel quadruplex

  2'-Deoxy-8-（propyn-1-yl）adenosine已掺入合成的寡脱氧核糖核苷酸中，并通过UV，CD和1H NMR研究了其对双链和四链结构热稳定性的影响。获得的结果似乎表明修饰的碱基的存在对双链DNA的稳定性有负面影响，而显着增加了平行四链体结构的稳定性。