1-propylinosine | 1042100-64-0

• 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-propylinosine
• 英文别名: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-propylpurin-6-one
• CAS: 1042100-64-0
• 化学式: C₁₃H₁₈N₄O₅
• 分子量: 310.31
• InChiKey: FHPZMJMDNAQQGJ-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  1-propylinosine 在 PO(OEt₅) 、 三氯氧磷 作用下， 生成 Phosphoric acid mono-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1-propyl-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester
  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：

  正丙胺 、 1-(2,4-dinitrophenyl)inosine 生成 1-propylinosine
  参考文献：
  名称：

  Synthesis of 4-N-alkyl and ribose-modified AICAR analogues on solid support

  摘要：

  Herein, we report the solid-phase synthesis of several 5-aminoimidazole-4-(N-alkyl)carboxamide-1-ribosides (4-N-alkyl AICARs) and the corresponding 2',3'-secoriboside derivatives. The method uses the N-1-dinitrophenyl-inosine 5'-bonded to a solid support. This inosine derivative has the C-2 of the purine base strongly activated towards the attack of N-nucleophiles thus allowing the preparation of several N-1 alkylated inosine supports from which a small library of 4-N-alkyl AICAR derivatives has been synthesized. A set of new 4-N-alkyl AICA-2',3'-secoriboside derivatives have also been obtained in high yields by solid-phase cleavage of the 2',3'-ribose bond. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.071

文献信息

• Synthesis of 4-N-alkyl and ribose-modified AICAR analogues on solid support
  作者：Giorgia Oliviero、Jussara Amato、Nicola Borbone、Stefano D'Errico、Gennaro Piccialli、Enrico Bucci、Vincenzo Piccialli、Luciano Mayol

  DOI：10.1016/j.tet.2008.04.071

  日期：2008.6

  Herein, we report the solid-phase synthesis of several 5-aminoimidazole-4-(N-alkyl)carboxamide-1-ribosides (4-N-alkyl AICARs) and the corresponding 2',3'-secoriboside derivatives. The method uses the N-1-dinitrophenyl-inosine 5'-bonded to a solid support. This inosine derivative has the C-2 of the purine base strongly activated towards the attack of N-nucleophiles thus allowing the preparation of several N-1 alkylated inosine supports from which a small library of 4-N-alkyl AICAR derivatives has been synthesized. A set of new 4-N-alkyl AICA-2',3'-secoriboside derivatives have also been obtained in high yields by solid-phase cleavage of the 2',3'-ribose bond. (c) 2008 Elsevier Ltd. All rights reserved.
• 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.