3'-azido-3'-deoxythymidin-5'-yl 4-methoxyphenyl hydroxy(pyridin-3-yl)methanephosphonate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-azido-3'-deoxythymidin-5'-yl 4-methoxyphenyl hydroxy(pyridin-3-yl)methanephosphonate
• 英文别名: 1-[(2R,4S,5S)-4-azido-5-[[[hydroxy(3-pyridyl)methyl]-(4-methoxyphenoxy)phosphoryl]oxymethyl]tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,4S,5S)-4-azido-5-[[[hydroxy(pyridin-3-yl)methyl]-(4-methoxyphenoxy)phosphoryl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₂₃H₂₅N₆O₈P
• 分子量: 544.461
• InChiKey: RARBEAXNPHLCPU-KTPBEUHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3'-azido-3'-deoxythymidin-5'-yl H-phosphonate monoester 在 吡啶 、 2,6-二甲基吡啶 、 氯磷酸二苯酯 作用下， 以 二氯甲烷 为溶剂， 反应 24.33h， 生成 3'-azido-3'-deoxythymidin-5'-yl 4-methoxyphenyl hydroxy(pyridin-3-yl)methanephosphonate
  参考文献：
  名称：

  Aryl nucleoside H-phosphonates. Part 15: Synthesis, properties and, anti-HIV activity of aryl nucleoside 5′-α-hydroxyphosphonates

  摘要：

  Aryl nucleoside 5'-H-phosphonates 4 bearing AZT or 2',3'-dideoxyuridine moieties were subjected to reaction with various aromatic aldehydes to produce nucleoside 5'-alpha-hydroxyphosphonate derivatives 2 as potential anti-HIV agents. Stability of the title compounds in cell culture media was investigated and three distinct decomposition pathways were identified. The anti-HIV activity of hydroxyphosplionates 2 correlates well with the type and extent of their chemical or enzymatic degradation in Culture medium (RPMI 1640 containing 10% FBS), suggesting that aryl nucleoside 5'-hydroxyphosphonates 2 act as depot forms of the parent antiviral nucleosides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.048

文献信息

• Aryl nucleoside H-phosphonates. Part 15: Synthesis, properties and, anti-HIV activity of aryl nucleoside 5′-α-hydroxyphosphonates
  作者：Agnieszka Szymańska、Marzena Szymczak、Jerzy Boryski、Jacek Stawiński、Adam Kraszewski、Gabriella Collu、Giseppina Sanna、Gabriele Giliberti、Roberta Loddo、Paolo La Colla

  DOI：10.1016/j.bmc.2005.10.048

  日期：2006.3

  Aryl nucleoside 5'-H-phosphonates 4 bearing AZT or 2',3'-dideoxyuridine moieties were subjected to reaction with various aromatic aldehydes to produce nucleoside 5'-alpha-hydroxyphosphonate derivatives 2 as potential anti-HIV agents. Stability of the title compounds in cell culture media was investigated and three distinct decomposition pathways were identified. The anti-HIV activity of hydroxyphosplionates 2 correlates well with the type and extent of their chemical or enzymatic degradation in Culture medium (RPMI 1640 containing 10% FBS), suggesting that aryl nucleoside 5'-hydroxyphosphonates 2 act as depot forms of the parent antiviral nucleosides. (c) 2005 Elsevier Ltd. All rights reserved.