2',3'-dideoxy-2',3'-didehydrouridin-5'-yl phenyl hydroxy(4-methoxyphenyl)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: 2',3'-dideoxy-2',3'-didehydrouridin-5'-yl phenyl hydroxy(4-methoxyphenyl)methanephosphonate
• 英文别名: 1-[(2R,4S,5S)-4-azido-5-[[[hydroxy-(4-methoxyphenyl)methyl]-phenoxy-phosphoryl]oxymethyl]tetrahydrofuran-2-yl]pyrimidine-2,4-dione；1-[(2R,4S,5S)-4-azido-5-[[[hydroxy-(4-methoxyphenyl)methyl]-phenoxyphosphoryl]oxymethyl]oxolan-2-yl]pyrimidine-2,4-dione
• 化学式: C₂₃H₂₄N₅O₈P
• 分子量: 529.446
• InChiKey: SFHMFQBOCNKXPH-ZKYKXKRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  [(2S,5R)-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxyphosphinic acid 在 吡啶 、 N,N-二异丙基乙胺 、 氯磷酸二苯酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 2',3'-dideoxy-2',3'-didehydrouridin-5'-yl phenyl hydroxy(4-methoxyphenyl)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.