9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-ethynylpurine | 91077-93-9

• 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: 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-ethynylpurine
• 英文别名: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-ethynyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-ethynylpurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 91077-93-9
• 化学式: C₁₈H₁₈N₄O₇
• 分子量: 402.364
• InChiKey: BITFPWFBQBSFLF-GFOCRRMGSA-N

物化性质

• 沸点：
  566.5±60.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-ethynylpurine 在 吡啶 、 N-氯代丁二酰亚胺 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 6-(3-methylisoxazol-5-yl)-9-(β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides

  摘要：

  Significant anti-HCV activity of 6-hetarylpurine ribonucleosides has been discovered and is reported here for the first time and compared with cytostatic effect. An extended series of 6-hetarylpurine ribonucleosides has been prepared by heterocyclizations in position 6 of purine nucleosides or by cross-couplings of 6-chloropurine nucleosides with hetarylboronic acids, -stannanes, or -zinc halides. The most anti-HCV active were purine ribonucleosides bearing pyrrol-3-yl (3k) or 2-furyl (3g) groups exerting EC90 = 0.14 and 0.4 mu M, respectively.

  DOI：

  10.1021/jm050335x
• 作为产物：
  描述：

  (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-((trimethylsilyl)ethynyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以43%的产率得到9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-ethynylpurine
  参考文献：
  名称：

  Expeditious synthesis and biological evaluation of new C-6 1,2,3-triazole adenosine derivatives A1 receptor antagonists or agonists

  摘要：

  描述了通过微波辅助的1,3-极性环加成反应合成新的C-6 1,2,3-三唑腺苷衍生物作为关键步骤。还评估了这些化合物对过表达A1腺苷受体（A1AR）细胞膜的结合效果。在这些化合物中，有四种在剂量依赖性方面增加cAMP的产生，作为A1AR的拮抗剂，而两种化合物则作为激动剂。

  DOI：

  10.1039/c0ob00017e

文献信息

• Revisiting the photochemical synthesis of [FeFe]-hydrogenase mimics: reaction optimization, mechanistic study and electrochemical behaviour
  作者：Sergio Aguado、Luis Casarrubios、Carmen Ramírez de Arellano、Miguel A. Sierra

  DOI：10.1039/d0ra06002j

  日期：——

  The photoreaction of [(μ-S)2Fe2(CO)6] and alkenes or alkynes has been optimized to readily obtain functionalized [FeFe]-hydrogenase mimics. Irradiation under low CO pressure in THF produces the corresponding photo-adducts in good/acceptable (alkenes/alkynes) yields, with retention of the starting olefin stereochemistry. DFT-calculations provide plausible reaction pathways in both, singlet and triplet

  [(μ-S) 2 Fe 2 (CO) 6 ] 和烯烃或炔烃的光反应已经过优化，可以很容易地获得功能化的 [FeFe]-氢化酶模拟物。在 THF 中的低 CO 压力下辐照以良好/可接受的（烯烃/炔烃）产率产生相应的光加合物，同时保留起始烯烃的立体化学。DFT 计算在单重态和三重态都提供了合理的反应途径。基于单线态的 DFT 计算在能量上更有利。还介绍了合成化合物的电化学行为，包括在酸性介质中的研究。产物的电化学性质在存在双键（[(μ-S) 2 Fe 2的环加成(CO) 6 ] 至炔烃），关于单键（环加成至烯烃）。
• Covalent Analogues of DNA Base-Pairs and Triplets VII. Synthesis and Cytostatic Activity of Bis(purin-6-yl)acetylene and -diacetylene Nucleosides
  作者：Petr Nauš、Ivan Votruba、Michal Hocek

  DOI：10.1135/cccc20041955

  日期：——

  The title bis(purin-6-yl)acetylene and -diacetylene nucleoside derivatives were prepared as covalent base-pair analogues starting from acyl-protected 6-ethynylpurine and 6-iodopurine nucleosides by the Sonogashira cross-coupling or oxidative alkyne-dimerization reactions followed by deprotection. The key starting acyl-protected 6-ethynylpurine nucleosides were prepared by a sequence of cross-coupling reactions of protected 6-halopurine nucleosides with (trimethylsilyl)acetylene followed by a modified desilylation with TBAF in presence of acetic acid. Surprisingly, the acyl-protected nucleosides exhibited significant cytostatic activity higher than the fully deprotected title compounds.

  标题为双(嘌呤-6-基)乙炔和-二乙炔核苷衍生物，通过Sonogashira交叉偶联或氧化炔基二聚反应起始于酰保护的6-乙炔基嘌呤和6-碘嘌呤核苷，然后进行去保护作用制备共价碱基对类似物。关键的起始酰保护的6-乙炔基嘌呤核苷是通过保护的6-卤代嘌呤核苷与(三甲基硅基)乙炔的交叉偶联反应序列，然后在存在乙酸的TBAF的修饰去硅化反应中制备的。令人惊讶的是，酰保护的核苷表现出显著的细胞增殖抑制活性，比完全去保护的标题化合物更高。