(2R,3R,5S)-2-(6-amino-2-((2-hydroxyethyl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol | 1504571-38-3

• 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: (2R,3R,5S)-2-(6-amino-2-((2-hydroxyethyl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol
• 英文别名: 2-(2-hydroxyethylamino)cordycepin；(2R,3R,5S)-2-[6-amino-2-(2-hydroxyethylamino)purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol
• CAS: 1504571-38-3
• 化学式: C₁₂H₁₈N₆O₄
• 分子量: 310.313
• InChiKey: VYTOUWCSIAAMRB-MVKOHCKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.55
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  151.57
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2-氟-6-氨基嘌呤 在 N,O-双三甲硅基乙酰胺 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 46.0h， 生成 (2R,3R,5S)-2-(6-amino-2-((2-hydroxyethyl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Structure–Activity Relationships of Synthetic Cordycepin Analogues as Experimental Therapeutics for African Trypanosomiasis

  摘要：

  Novel methods for treatment of African trypanosomiasis, caused by infection with Trypanosoma brucei are needed. Cordycepin (3'-deoxyadenosine, la) is a powerful trypanocidal compound in vitro but is ineffective in vivo because of rapid metabolic,degradation by adenosine deaminase (ADA). We elucidated the structural moieties of cordycepin required for trypanocidal activity and designed analogues that retained trypanotoxicity while gaining resistance to ADA-mediated metabolism. 2-Fluorocordycepin (2-fluoro3'-deoxyadenosine, 1b) was identified as a selective, potent, and ADA-resistant trypanocidal compound that cured T. brucei infection in mice. Compound 1b is transported through the high affinity TbAT1/P2 adenosine transporter and is a substrate of T. b. brucei adenosine kinase. 1b has good preclinical properties suitable for an, oral drug, albeit a relatively short plasma half-life. We present a rapid and efficient synthesis of 2-halogenated cordycepins, also useful synthons. for the development of additional novel C2-substituted 3'-deoxyadenosine analogues to be evaluated in development of experimental therapeutics.

  DOI：

  10.1021/jm401530a