3'-azido-3'-deoxythymidin-5'-yl pyridin-3-yl pyridin-4-yl phosphate | 1162085-68-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 3'-azido-3'-deoxythymidin-5'-yl pyridin-3-yl pyridin-4-yl phosphate
• 英文别名: [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl 3-pyridyl 4-pyridyl phosphate；[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl pyridin-3-yl pyridin-4-yl phosphate
• CAS: 1162085-68-8
• 化学式: C₂₀H₂₀N₇O₇P
• 分子量: 501.395
• InChiKey: KULRRPVKRXFPKB-IYKQBRMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3'-azido-3'-deoxythymidin-5'-yl pyridin-3-yl pyridin-4-yl phosphate 在 水 作用下， 生成 3'-azido-3'-deoxythymidin-5'-yl pyridin-3-yl phosphate
  参考文献：
  名称：

  Aryl nucleoside H-phosphonates. Part 16: Synthesis and anti-HIV-1 activity of di-aryl nucleoside phosphotriesters

  摘要：

  Di-aryl nucleoside phosphotriesters have been explored as a new type of pronucleotides for the purpose of anti-HIV-1 therapy and efficient synthetic protocols, based on H-phosphonate chemistry, have been developed for the preparation of this class of compounds. It was found that anti-HIV-1 activity of the phosphotriesters bearing an antiviral nucleoside moiety (AZT, ddA) and also ddU was due, at least partially, to intracellular conversion into the corresponding nucleoside 5'-monophosphates, and their efficiency correlated well with the pK(a) values of the aryloxy groups present. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.033
• 作为产物：
  描述：

  3-羟基吡啶 、 ((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl pyridin-4-yl phosphonate 在 吡啶 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以0.07 g的产率得到3'-azido-3'-deoxythymidin-5'-yl pyridin-3-yl pyridin-4-yl phosphate
  参考文献：
  名称：

  Aryl nucleoside H-phosphonates. Part 16: Synthesis and anti-HIV-1 activity of di-aryl nucleoside phosphotriesters

  摘要：

  Di-aryl nucleoside phosphotriesters have been explored as a new type of pronucleotides for the purpose of anti-HIV-1 therapy and efficient synthetic protocols, based on H-phosphonate chemistry, have been developed for the preparation of this class of compounds. It was found that anti-HIV-1 activity of the phosphotriesters bearing an antiviral nucleoside moiety (AZT, ddA) and also ddU was due, at least partially, to intracellular conversion into the corresponding nucleoside 5'-monophosphates, and their efficiency correlated well with the pK(a) values of the aryloxy groups present. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.033

文献信息

• Aryl nucleoside H-phosphonates. Part 16: Synthesis and anti-HIV-1 activity of di-aryl nucleoside phosphotriesters
  作者：Joanna Romanowska、Agnieszka Szymańska-Michalak、Jerzy Boryski、Jacek Stawiński、Adam Kraszewski、Roberta Loddo、Giuseppina Sanna、Gabriella Collu、Barbara Secci、Paolo La Colla

  DOI：10.1016/j.bmc.2009.02.033

  日期：2009.5

  Di-aryl nucleoside phosphotriesters have been explored as a new type of pronucleotides for the purpose of anti-HIV-1 therapy and efficient synthetic protocols, based on H-phosphonate chemistry, have been developed for the preparation of this class of compounds. It was found that anti-HIV-1 activity of the phosphotriesters bearing an antiviral nucleoside moiety (AZT, ddA) and also ddU was due, at least partially, to intracellular conversion into the corresponding nucleoside 5'-monophosphates, and their efficiency correlated well with the pK(a) values of the aryloxy groups present. (C) 2009 Elsevier Ltd. All rights reserved.