1-propargylinosine

• 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: 1-propargylinosine
• 英文别名: 1-Propargylinosine；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-prop-2-ynylpurin-6-one
• 化学式: C₁₃H₁₄N₄O₅
• 分子量: 306.278
• InChiKey: KABSKGNCJOWPEI-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  22
• 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：
  120
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-溴丙炔 、 肌苷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以94.6%的产率得到1-propargylinosine
  参考文献：
  名称：

  “SENSELESS” ANTIVIRAL POLYRIBONUCLEOTIDES: POLY (1-PROPARGYLINOSINIC ACID)

  摘要：

  Previous work has shown that novel amphipathic oligo and polyribonucleotides exhibiting secondary structure in solution are potent inhibitors of HIV and HCMV replication and cytopathicity in tissue culture. It was hypothesized that the mechanism(s) of action for these compounds might be inhibition of retroviral reverse transcriptase (RT) and/or viral uptake by cells. Pursuit of the essential pharmacophore has led to the discovery of poly (1-propargylinosinic acid) (10), an HIV and HCMV-active polyribonucleotide lacking the secondary structure previously thought to be essential for the observed antiviral activity.

  DOI：

  10.1081/ncn-120006529

文献信息

• Amphipathic oligonucleotides and polynucleotides having potent antiviral
  申请人：University of Utah Research Foundation

  公开号：US06130324A1

  公开（公告）日：2000-10-10

  The present invention provides novel compositions that show potent antiviral activity against both DNA and RNA viruses. In particular, the present invention provides oligo- and polyribonucleotides with potent antiviral activity against HIV and HCMV. These compositions are thought to operate in a novel fashion at an early stage of viral infection, meeting the need for alternatives or synergistic therapies to the toxic treatments currently available. The present invention also discloses methods for synthesizing oligo- and polyribonucleotides showing antiviral activity.

  本发明提供了新型组合物，对DNA和RNA病毒均具有强效的抗病毒活性。特别地，本发明提供了具有强效抗HIV和HCMV病毒活性的寡核苷酸和多核苷酸。这些组合物被认为在病毒感染的早期阶段以一种新颖的方式发挥作用，满足了对于替代或协同治疗目前可用的有毒治疗的需求。本发明还揭示了合成具有抗病毒活性的寡核苷酸和多核苷酸的方法。
• “SENSELESS” ANTIVIRAL POLYRIBONUCLEOTIDES: POLY (1-PROPARGYLINOSINIC ACID)
  作者：Robyn M. Hyde、Robert W. Buckheit、Arthur D. Broom

  DOI：10.1081/ncn-120006529

  日期：2002.4.15

  Previous work has shown that novel amphipathic oligo and polyribonucleotides exhibiting secondary structure in solution are potent inhibitors of HIV and HCMV replication and cytopathicity in tissue culture. It was hypothesized that the mechanism(s) of action for these compounds might be inhibition of retroviral reverse transcriptase (RT) and/or viral uptake by cells. Pursuit of the essential pharmacophore has led to the discovery of poly (1-propargylinosinic acid) (10), an HIV and HCMV-active polyribonucleotide lacking the secondary structure previously thought to be essential for the observed antiviral activity.