1-[2-deoxy-β-D-erythro-pentofuranosyl]3-{3-[bis(1-benzyl-1',2',3'-triazol-4-ylmethyl)amino]prop-1-ynyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine | 1333407-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 1-[2-deoxy-β-D-erythro-pentofuranosyl]3-{3-[bis(1-benzyl-1',2',3'-triazol-4-ylmethyl)amino]prop-1-ynyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• 英文别名: (2R,3S,5R)-5-[4-amino-3-[3-[bis[(1-benzyltriazol-4-yl)methyl]amino]prop-1-ynyl]pyrazolo[3,4-d]pyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 1333407-06-9
• 化学式: C₃₃H₃₄N₁₂O₃
• 分子量: 646.712
• InChiKey: SMNSPUWFGKTQSP-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  184
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  1-(2-deoxy-β-D-erythro-pentofuranosyl)-3-[di(prop-2-ynyl)amino]prop-1-ynyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 、 苄基叠氮 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以76%的产率得到1-[2-deoxy-β-D-erythro-pentofuranosyl]3-{3-[bis(1-benzyl-1',2',3'-triazol-4-ylmethyl)amino]prop-1-ynyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine
  参考文献：
  名称：

  Hydrogelation and spontaneous fiber formation of 8-aza-7-deazaadenine nucleoside ‘click’ conjugates

  摘要：

  Nucleoside hydrogels based on benzyl azide 'click' conjugates of 8-aza-7-deaza-2'-deoxyadenosine bearing 7-ethynyl, 7-octa-(1,7-diynyl), and 7-tri-prop-2-ynyl-amine side chains were synthesized (1, 3, 4). The cycloaddition adduct with the shortest linker (1) yields the most powerful hydrogelator forming stable gels at a concentration of 0.3 wt % of 1 in water. One molecule of 1 catches 7500 water molecules. Cycloaddition of the 8-aza-7-deaza-7-azido-2'-deoxyadenosine (9) and 3-phenyl-1-propyne (10) leads to the isomeric conjugate 2, with a C-N connectivity between the nucleobase and triazole moiety. This gel is less stable than that of the adduct 1. Both gels show a similar stability over a wide pH range (4.0-10.0). Xerogels of 1 and 2 studied by scanning electron microscopy (SEM) reveal that both click adducts (1 and 2) form long fibers spontaneously. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.015