N¹-allylinosine | 146797-61-7

• 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: N¹-allylinosine
• 英文别名: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-prop-2-enylpurin-6-one
• CAS: 146797-61-7
• 化学式: C₁₃H₁₆N₄O₅
• 分子量: 308.294
• InChiKey: ZMIKUOIPWKLCBM-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  4
• 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

• 作为反应物：
  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
• 作为产物：
  描述：

  3-溴丙烯 、 肌苷 在 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N¹-allylinosine
  参考文献：
  名称：

  Nucleosides and nucleotides. 115. Synthesis of 3-alkyl-3-deazainosines via palladium-catalyzed intramolecular cyclization: A new conformational lock wi

  摘要：

  Synthesis of 3-methyl-3-deazainosine (7a) and 3-ethyl-3-deazainosine (7b) can be done by intramolecular cyclization of 5-iodoimidazole-4-(N-allyl and -crotyl)carboxamide ribosides 4a,b with palladium catalysts. The glycosyl conformer population of 7a,b was analyzed by NOE experiments to be fixed in anti-conformation.

  DOI：

  10.1016/s0040-4039(00)60068-0

文献信息

• Microwave-Assisted Selective 5′-<i>O</i>-Trityl Protection of Inosine Derivatives
  作者：C. Kappe、Elena Casanova、María-Jesús Pérez-Pérez

  DOI：10.1055/s-2007-982532

  日期：2007.7

  The efficient microwave-assisted synthesis of 5′- O-trityl inosine derivatives is described. The reported protocol allows the protection of inosine derivatives in significantly higher yields and shorter reaction times than the standard thermal conditions. This procedure is particularly suitable for modified inosines where the 5′-OH is sterically hindered (i.e. 8-bromoinosine).

  描述了 5'-O-三苯甲基肌苷衍生物的高效微波辅助合成。报告的协议允许以比标准热条件显着更高的产率和更短的反应时间保护肌苷衍生物。该程序特别适用于 5'-OH 位阻的修饰肌苷（即 8-溴肌苷）。
• 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.
• Nucleosides and nucleotides. 115. Synthesis of 3-alkyl-3-deazainosines via palladium-catalyzed intramolecular cyclization: A new conformational lock wi
  作者：Mitsutoshi Aoyagi、Noriaki Minakawa、Akira Matsuda

  DOI：10.1016/s0040-4039(00)60068-0

  日期：1993.1

  Synthesis of 3-methyl-3-deazainosine (7a) and 3-ethyl-3-deazainosine (7b) can be done by intramolecular cyclization of 5-iodoimidazole-4-(N-allyl and -crotyl)carboxamide ribosides 4a,b with palladium catalysts. The glycosyl conformer population of 7a,b was analyzed by NOE experiments to be fixed in anti-conformation.