8-(3-pyridyl)inosine | 1616667-84-5

• 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: 8-(3-pyridyl)inosine
• 英文别名: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-pyridin-3-yl-1H-purin-6-one
• CAS: 1616667-84-5
• 化学式: C₁₅H₁₅N₅O₅
• 分子量: 345.315
• InChiKey: CQSSECWNFCITFD-ORXWAGORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2',3'-O-异丙叉肌苷 在 哌啶 、 copper(l) iodide 、 palladium diacetate 、 caesium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 8-(3-pyridyl)inosine
  参考文献：
  名称：

  Microwave-assisted synthesis of C-8 aryl and heteroaryl inosines and determination of their inhibitory activities against Plasmodium falciparum purine nucleoside phosphorylase

  摘要：

  8-Arylinosines have been scarcely studied for therapeutic purposes, probably due to difficulties in their synthesis. The recently described direct arylation reaction at position 8 of purine nucleosides has been employed to synthesize a series of 8-aryl and 8-pyridylinosines. These compounds have been studied for hydrolytic stability and subjected to biological evaluation. Three compounds have shown a pronounced specific inhibition of Plasmodium falciparum-encoded purine nucleoside phosphorylase, an important target for antimalarial chemotherapy. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.073

文献信息

• Microwave-assisted synthesis of C-8 aryl and heteroaryl inosines and determination of their inhibitory activities against Plasmodium falciparum purine nucleoside phosphorylase
  作者：Alba Gigante、Eva-María Priego、Paula Sánchez-Carrasco、Luis Miguel Ruiz-Pérez、Johan Vande Voorde、María- José Camarasa、Jan Balzarini、Dolores González-Pacanowska、María-Jesús Pérez-Pérez

  DOI：10.1016/j.ejmech.2014.05.073

  日期：2014.7

  8-Arylinosines have been scarcely studied for therapeutic purposes, probably due to difficulties in their synthesis. The recently described direct arylation reaction at position 8 of purine nucleosides has been employed to synthesize a series of 8-aryl and 8-pyridylinosines. These compounds have been studied for hydrolytic stability and subjected to biological evaluation. Three compounds have shown a pronounced specific inhibition of Plasmodium falciparum-encoded purine nucleoside phosphorylase, an important target for antimalarial chemotherapy. (C) 2014 Elsevier Masson SAS. All rights reserved.