(1R,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-((S)-2-hydroxypropyl)cyclopentane-1,2-diol | 1443988-15-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1R,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-((S)-2-hydroxypropyl)cyclopentane-1,2-diol
• 英文别名: (1R,2S,3R,5R)-3-(6-aminopurin-9-yl)-5-[(2S)-2-hydroxypropyl]cyclopentane-1,2-diol
• CAS: 1443988-15-5
• 化学式: C₁₃H₁₉N₅O₃
• 分子量: 293.326
• InChiKey: GKBQORWUVIAVKO-PTPLXHBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(3aR,4R,6R,6aS)-6-(6-Chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-acetic acid ethyl ester 在 盐酸 、 氨 、 二异丁基氢化铝 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 54.5h， 生成 (1R,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-((S)-2-hydroxypropyl)cyclopentane-1,2-diol
  参考文献：
  名称：

  6′-Methyl-5′-homoaristeromycin: A structural variation of the anti-orthopox virus candidate 5′-homoaristeromycin

  摘要：

  The synthesis of 6'-methyl-5'-homoaristeromycin is described from a known 6'-ethyl ester. Antiviral analysis showed the (S)-6' stereoisomer retained the vaccinia activity of the parent 5'-homoaristeromycin (1) while the (R)-6' isomer was less active. Both were weaker than 1 towards cowpox. The diastereomers were equally active versus Epstein Barr virus while (S)-6' was three times more active toward vesicular stomatitis virus than (R)-6'. The diastereomers were inactive towards numerous other viruses. The CC50 for both diastereomers was >300 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.070

文献信息

• The metathesis reaction for side chain construction in carbocyclic sinefungin analogue synthesis
  作者：Qi Chen、Chong Liu、Tetyana S. Shulyak、Stewart W. Schneller

  DOI：10.1016/j.tet.2013.12.030

  日期：2014.1

  The naturally occurring nucleoside sinefungin has found considerable use in biological investigations. More extensive sinefungin studies have been limited because few analogues have been reported due to the synthetic challenges associated with such studies. Reported herein are preparative ways to two carbocyclic sinefungin analogues: 6'-deaminocarbocyclic sinefungin and (S)-6'-hydroxy-6'-deamino-carbocyclic sinefimgin. The synthetic routes were made efficient and practical by the application of two metathesis reactions employing second generation Grubbs catalyst. (C) 2013 Elsevier Ltd. All rights reserved.
• 6′-Methyl-5′-homoaristeromycin: A structural variation of the anti-orthopox virus candidate 5′-homoaristeromycin
  作者：Minmin Yang、Wei Ye、Stewart W. Schneller

  DOI：10.1016/j.bmc.2013.04.070

  日期：2013.7

  The synthesis of 6'-methyl-5'-homoaristeromycin is described from a known 6'-ethyl ester. Antiviral analysis showed the (S)-6' stereoisomer retained the vaccinia activity of the parent 5'-homoaristeromycin (1) while the (R)-6' isomer was less active. Both were weaker than 1 towards cowpox. The diastereomers were equally active versus Epstein Barr virus while (S)-6' was three times more active toward vesicular stomatitis virus than (R)-6'. The diastereomers were inactive towards numerous other viruses. The CC50 for both diastereomers was >300 mu M. (C) 2013 Elsevier Ltd. All rights reserved.