2',3'-dideoxyinosine-5'-yl-O-ethyl carbonate

• 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: 2',3'-dideoxyinosine-5'-yl-O-ethyl carbonate
• 英文别名: ethyl [(2S,5R)-5-(6-oxo-3H-purin-9-yl)tetrahydrofuran-2-yl]methyl carbonate；ethyl [(2S,5R)-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl carbonate
• 化学式: C₁₃H₁₆N₄O₅
• 分子量: 308.294
• InChiKey: LYWWKMDQMJNNJN-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2',3'-二脱氧肌苷 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2',3'-dideoxyinosine-5'-yl-O-ethyl carbonate
  参考文献：
  名称：

  Biological evaluation and molecular modelling of didanosine derivatives

  摘要：

  这些具有增加脂溶性和良好抗病毒性能的DDI前药应该在HIV治疗中引起关注。

  DOI：

  10.1039/c4md00003j

文献信息

• Ether, Carbonate and Urethane Deoxynucleoside Derivatives as Prodrugs.
  作者：Kristin Hammer、Jostein Hatlelid、Morten Grøtli、Joseph Arukwe、Jo Klaveness、Frode Rise、Kjell Undheim、Connie N. Rosendahl、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0609

  日期：——

  3'-Deoxythymidine and its 3'-azido derivative, 2',3'-dideoxycytidine, 2',3'-dideoxyinosine and 2',3'-dideoxyadenosine have been acylated to form carbonates and methanes in chemoselective reactions. The nucleosides have been N- and/or O-alkylated by alpha-chloroethyl or chloromethyl alkyl carbonates to form alpha-alkyloxycarbonyloxyethyl or alkyloxycarbonyloxymethyl derivatives. The products are lipophilic in order to facilitate transport through biological membranes and are designed to be cleaved by esterases with liberation of the bioactive nucleoside. Initial esterase cleavage of the alkylated derivatives produces hemiacetals or -aminals which subsequently dissociate to the active nucleoside.
• Biological evaluation and molecular modelling of didanosine derivatives
  作者：Soledad Ravetti、Cristian A. De Candia、María S. Gualdesi、Sandra Pampuro、Gabriela Turk、Mario A. Quevedo、Margarita C. Briñón

  DOI：10.1039/c4md00003j

  日期：——

  These prodrugs of DDI with increased lipophilicity and good antiviral performance should be of interest in HIV therapy.

  这些具有增加脂溶性和良好抗病毒性能的DDI前药应该在HIV治疗中引起关注。