4-butanoyloxybenzyl bis(3'-azido-3'-deoxythymidin-5-yl) phosphate | 171284-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-butanoyloxybenzyl bis(3'-azido-3'-deoxythymidin-5-yl) phosphate
• 英文别名: [4-[bis[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryloxymethyl]phenyl] butanoate
• CAS: 171284-24-5
• 化学式: C₃₁H₃₇N₁₀O₁₂P
• 分子量: 772.668
• InChiKey: NZVNXRMOYNPSIM-XOGRSFEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  54
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  217
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4-butanoyloxybenzyl bis(3'-azido-3'-deoxythymidin-5-yl) phosphate 以 重水 为溶剂， 反应 120.0h， 生成 齐多夫定 、 3'-azido-2',3'-dideoxythymidine monophosphate 、 bis(3'-azido-3'-deoxy-5'-thymidinyl) phosphate
  参考文献：
  名称：

  Synthesis, Bioactivation and Anti-HIV Activity of 4-Acyloxybenzylbis(Nucleosid-5′-yl) Phosphates

  摘要：

  4-Acyloxybenzyl bis(nucleosid-5'-yl) phosphates 7a-c and 9a-c were prepared as potential prodrugs of the anti-HIV nucleosides 3'-azido-3'-deoxythymidine (AZT) and 2',3'-dideoxyinosine (ddI) or their 5'-monophosphates.The anti-HIV activities of these triesters were determined in two T-cell lines. In a C8165 cell line they displayed activities comparable to and in some cases superior to AZT, but they also exhibited an increase in cytotoxicity. In a thymidine kinase deficient JM T-cell line the activity was reduced but was still superior to AZT. In the presence of porcine liver carboxyesterase (PLCE), triester 7b biodegrades to the diester 10 which, with phosphodiesterase, gives initially AZT monophosphate 3 and AZT.

  DOI：

  10.1080/15257779508009491
• 作为产物：
  描述：

  4-(hydroxymethyl)phenyl butyrate 在 四氮唑 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 生成 4-butanoyloxybenzyl bis(3'-azido-3'-deoxythymidin-5-yl) phosphate
  参考文献：
  名称：

  Synthesis, Bioactivation and Anti-HIV Activity of 4-Acyloxybenzylbis(Nucleosid-5′-yl) Phosphates

  摘要：

  4-Acyloxybenzyl bis(nucleosid-5'-yl) phosphates 7a-c and 9a-c were prepared as potential prodrugs of the anti-HIV nucleosides 3'-azido-3'-deoxythymidine (AZT) and 2',3'-dideoxyinosine (ddI) or their 5'-monophosphates.The anti-HIV activities of these triesters were determined in two T-cell lines. In a C8165 cell line they displayed activities comparable to and in some cases superior to AZT, but they also exhibited an increase in cytotoxicity. In a thymidine kinase deficient JM T-cell line the activity was reduced but was still superior to AZT. In the presence of porcine liver carboxyesterase (PLCE), triester 7b biodegrades to the diester 10 which, with phosphodiesterase, gives initially AZT monophosphate 3 and AZT.

  DOI：

  10.1080/15257779508009491

文献信息

• Synthesis, Bioactivation and Anti-HIV Activity of 4-Acyloxybenzyl<i>bis</i>(Nucleosid-5′-yl) Phosphates
  作者：Anne Routledge、Ian Walker、Sally Freeman、Alan Hay、Naheed Mahmood

  DOI：10.1080/15257779508009491

  日期：1995.9

  4-Acyloxybenzyl bis(nucleosid-5'-yl) phosphates 7a-c and 9a-c were prepared as potential prodrugs of the anti-HIV nucleosides 3'-azido-3'-deoxythymidine (AZT) and 2',3'-dideoxyinosine (ddI) or their 5'-monophosphates.The anti-HIV activities of these triesters were determined in two T-cell lines. In a C8165 cell line they displayed activities comparable to and in some cases superior to AZT, but they also exhibited an increase in cytotoxicity. In a thymidine kinase deficient JM T-cell line the activity was reduced but was still superior to AZT. In the presence of porcine liver carboxyesterase (PLCE), triester 7b biodegrades to the diester 10 which, with phosphodiesterase, gives initially AZT monophosphate 3 and AZT.