((2R,3R,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3-((methylsulfonyl)oxy)-4-(pivaloyloxy)tetrahydrofuran-2-yl)methyl pivalate | 1504571-53-2

• 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,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3-((methylsulfonyl)oxy)-4-(pivaloyloxy)tetrahydrofuran-2-yl)methyl pivalate
• CAS: 1504571-53-2
• 化学式: C₂₁H₃₀FN₅O₈S
• 分子量: 531.562
• InChiKey: NOYNQZYEJGJPDP-XNIJJKJLSA-N

反应信息

• 作为反应物：
  描述：

  ((2R,3R,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3-((methylsulfonyl)oxy)-4-(pivaloyloxy)tetrahydrofuran-2-yl)methyl pivalate 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成
  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
• 作为产物：
  描述：

  三甲基乙酰氯 、 2-氟腺苷 、 甲基磺酰氯 在 吡啶 作用下， 反应 5.0h， 生成 ((2R,3R,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3-((methylsulfonyl)oxy)-4-(pivaloyloxy)tetrahydrofuran-2-yl)methyl pivalate
  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