8-(4"-methylphenyl)inosine | 81841-12-5

• 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-(4"-methylphenyl)inosine
• 英文别名: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-(4-methylphenyl)-1H-purin-6-one
• CAS: 81841-12-5
• 化学式: C₁₇H₁₈N₄O₅
• 分子量: 358.354
• InChiKey: PHQAKDSMEGYNRL-CNEMSGBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2',3'-O-isopropylidene-8-(4"-toly)inosine 在 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.25h， 以87%的产率得到8-(4"-methylphenyl)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

• Hung, Ming-Hong; Stock, Leon M., Heterocycles, 1982, vol. 18, p. 67 - 75
  作者：Hung, Ming-Hong、Stock, Leon M.

  DOI：——

  日期：——
• 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.