(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-[[[1-(1,3-thiazol-2-yl)pyrrol-2-yl]methylamino]-methyl]oxolane-3,4-diol | 1222420-80-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-[[[1-(1,3-thiazol-2-yl)pyrrol-2-yl]methylamino]-methyl]oxolane-3,4-diol
• 英文别名: (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-[[[1-(1,3-thiazol-2-yl)pyrrol-2-yl]methylamino]methyl]oxolane-3,4-diol
• CAS: 1222420-80-5
• 化学式: C₁₈H₂₀N₈O₃S
• 分子量: 428.475
• InChiKey: PDANHRLXDXYIQD-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 sodium tetrahydroborate 、 甲酸 、 偶氮二甲酸二异丙酯 、 水 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 5.5h， 生成 (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-[[[1-(1,3-thiazol-2-yl)pyrrol-2-yl]methylamino]-methyl]oxolane-3,4-diol
  参考文献：
  名称：

  Parallel Solution-Phase Synthesis of an Adenosine Antibiotic Analog Library

  摘要：

  A library of eighty one adenosine antibiotic analogs was prepared under the Pilot Scale Library Program of the NIH Roadmap initiative from 5'-amino-5'-deoxy-2',3'-O-isopropylidene-adenosine 3. Diverse aldehyde, sulfonyl chloride and carboxylic acid reactant sets were condensed to 3, in solution-phase fashion, leading after acid-mediated hydrolysis to the targeted compounds in good yields and high purity. No marked antituberculosis or anticancer activity was noted on preliminary cellular testing, but these nucleoside analogs should be useful candidates for other types of biological activity.

  DOI：

  10.1021/co300127z

文献信息

• Parallel Solution-Phase Synthesis of an Adenosine Antibiotic Analog Library
  作者：Omar Moukha-chafiq、Robert C. Reynolds

  DOI：10.1021/co300127z

  日期：2013.3.11

  A library of eighty one adenosine antibiotic analogs was prepared under the Pilot Scale Library Program of the NIH Roadmap initiative from 5'-amino-5'-deoxy-2',3'-O-isopropylidene-adenosine 3. Diverse aldehyde, sulfonyl chloride and carboxylic acid reactant sets were condensed to 3, in solution-phase fashion, leading after acid-mediated hydrolysis to the targeted compounds in good yields and high purity. No marked antituberculosis or anticancer activity was noted on preliminary cellular testing, but these nucleoside analogs should be useful candidates for other types of biological activity.