1-allylinosine-5'-monophosphate | 532930-91-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 1-allylinosine-5'-monophosphate
• 英文别名: [(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1-prop-2-enylpurin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate
• CAS: 532930-91-9
• 化学式: C₁₃H₁₇N₄O₈P
• 分子量: 388.274
• InChiKey: HEGLBNQYBKXWDX-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  167
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-allylinosine-5'-monophosphate 在 N,N'-羰基二咪唑 、 butylamine phosphoric acid salt 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以15.4%的产率得到1-allylinosine-5'-diphosphate
  参考文献：
  名称：

  Antiviral Amphipathic Oligo- and Polyribonucleotides:  Analogue Development and Biological Studies

  摘要：

  A series of novel N1 alkylated purine nucleic acids were polymerized either enzymatically or by automated synthesis to further establish the SAR requirements for HIV, RT, and HCMV activity. Out of the series, two constructs, 2'-O-methyl-1-allylinosinic acid phosphorothioate 33-mer (16) and an oligomer incorporating 1-propyl-6-thioinosinic acid residues (20), were found to be highly active under all three assay conditions. SAR studies indicate that sulfur incorporation, high molecular weight, and low steric bulk at N1 all can be important for activity.

  DOI：

  10.1021/jm0203276
• 作为产物：
  描述：

  N¹-allylinosine 在 PO(OEt₅) 、 三氯氧磷 作用下， 以83%的产率得到1-allylinosine-5'-monophosphate
  参考文献：
  名称：

  Antiviral Amphipathic Oligo- and Polyribonucleotides:  Analogue Development and Biological Studies

  摘要：

  A series of novel N1 alkylated purine nucleic acids were polymerized either enzymatically or by automated synthesis to further establish the SAR requirements for HIV, RT, and HCMV activity. Out of the series, two constructs, 2'-O-methyl-1-allylinosinic acid phosphorothioate 33-mer (16) and an oligomer incorporating 1-propyl-6-thioinosinic acid residues (20), were found to be highly active under all three assay conditions. SAR studies indicate that sulfur incorporation, high molecular weight, and low steric bulk at N1 all can be important for activity.

  DOI：

  10.1021/jm0203276

文献信息

• Antiviral Amphipathic Oligo- and Polyribonucleotides:  Analogue Development and Biological Studies
  作者：Robyn M. Hyde、Arthur D. Broom、Robert W. Buckheit

  DOI：10.1021/jm0203276

  日期：2003.5.1

  A series of novel N1 alkylated purine nucleic acids were polymerized either enzymatically or by automated synthesis to further establish the SAR requirements for HIV, RT, and HCMV activity. Out of the series, two constructs, 2'-O-methyl-1-allylinosinic acid phosphorothioate 33-mer (16) and an oligomer incorporating 1-propyl-6-thioinosinic acid residues (20), were found to be highly active under all three assay conditions. SAR studies indicate that sulfur incorporation, high molecular weight, and low steric bulk at N1 all can be important for activity.