N²-isobutyryl acyclovir | 205533-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N²-isobutyryl acyclovir
• 英文别名: N-[9-(2-hydroxyethoxymethyl)-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 205533-48-8
• 化学式: C₁₂H₁₇N₅O₄
• 分子量: 295.298
• InChiKey: WSZYKCOHFOVLPH-UHFFFAOYSA-N

物化性质

• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N²-isobutyryl acyclovir 在 四氮唑 、 ammonium hydroxide 、 lipozyme 、 Dowex-50 W resin (TBA form) 、 碘 、 溶剂黄146 作用下， 反应 48.0h， 生成 Hexadecanoic acid (R)-3-{[2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethoxy]-hydroxy-phosphoryloxy}-2-hydroxy-propyl ester
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Lysophosphatidylnucleosides

  摘要：

  5'-O-Lysophosphatidylnucleosides [5'-O-(1-O-acyl-sn-glycero-3-phosphoryl)nucleosides] were obtained by a two-step chemoenzymatic synthesis. 5'-O-(sn-Glycero-3-phosphoryl)nucleosides (5'-GPNs) were first prepared from a phosphoramidite of 1,2-O-isopropylidene-sn-glycerol and appropriately protected nucleosides, applying the phosphoramidite methodology on the solid phase or in solution. In a following step, the regioselective acylation at the C-l hydroxyl of the glycerol moiety of 5'-GPNs was achieved by a lipase-catalyzed transacylation with activated fatty acid esters in organic solvent. Some deoxyribo- and ribonucleosides, as well, were converted into the corresponding lysophosphatidyl derivatives utilizing either saturated or unsaturated fatty acid esters with different length alkyl chains. The synthesis was also applied to the preparation of O-(1-O-palmitoyl-sn-glycero-3-phosphoryl) conjugates of Acyclovir and AZT, of potential pharmacological interest.

  DOI：

  10.1021/jo971826v
• 作为产物：
  描述：

  阿昔洛韦 、 异丁酰氯 在 吡啶 作用下， 反应 5.25h， 以53%的产率得到N²-isobutyryl acyclovir
  参考文献：
  名称：

  [EN] NANOPARTICLE COMPOSITIONS
  [FR] COMPOSITIONS DE NANOPARTICULES

  摘要：

  本公开提供了包含核苷酸或核苷酸前药的纳米粒子组合物，它们作为药物剂的用途以及其制备过程。本公开还提供了将本文描述的纳米粒子组合物用作药物和/或用于制造用于治疗各种疾病，包括癌症和病毒感染的药物的方法。在一方面提供了一种包含纳米粒子的组合物，其中纳米粒子包含核苷酸或核苷酸的前药，以及药用可接受载体；其中药用可接受载体包括白蛋白。

  公开号：

  WO2019169324A1

文献信息

• Acyclovir terminated thiophosphate dendrimers
  作者：Grzegorz M. Salamończyk

  DOI：10.1016/j.tetlet.2003.08.035

  日期：2003.9

  An efficient synthesis of antiviral dendritic prodrug candidates, water-soluble, polyanionic conjugates of 1st and 2nd generation thiophosphate dendrimers with acyclovir, is described. (C) 2003 Elsevier Ltd. All rights reserved.
• NANOPARTICLE COMPOSITIONS
  申请人：January Therapeutics, Inc.

  公开号：US20210007999A1

  公开（公告）日：2021-01-14

  This disclosure provides nanoparticle compositions comprising nucleoside or nucleotide prodrugs, their use as medicinal agents, and processes for their preparation. The disclosure also provides for the use of the nanoparticle compositions described herein as medicaments and/or in the manufacture of medicaments for the treatment of a variety of diseases, including cancer and viral infections. Provided in one aspect is a composition comprising nanoparticles, wherein the nanoparticles comprise a prodrug of a nucleoside or nucleotide, and a pharmaceutically acceptable carrier; wherein the pharmaceutically acceptable carrier comprises albumin.
• [EN] NANOPARTICLE COMPOSITIONS<br/>[FR] COMPOSITIONS DE NANOPARTICULES
  申请人：JANUARY THERAPEUTICS INC

  公开号：WO2019169324A1

  公开（公告）日：2019-09-06

  This disclosure provides nanoparticle compositions comprising nucleoside or nucleotide prodrugs, their use as medicinal agents, and processes for their preparation. The disclosure also provides for the use of the nanoparticle compositions described herein as medicaments and/or in the manufacture of medicaments for the treatment of a variety of diseases, including cancer and viral infections. Provided in one aspect is a composition comprising nanoparticles, wherein the nanoparticles comprise a prodrug of a nucleoside or nucleotide, and a pharmaceutically acceptable carrier; wherein the pharmaceutically acceptable carrier comprises albumin.

  本公开提供了包含核苷酸或核苷酸前药的纳米粒子组合物，它们作为药物剂的用途以及其制备过程。本公开还提供了将本文描述的纳米粒子组合物用作药物和/或用于制造用于治疗各种疾病，包括癌症和病毒感染的药物的方法。在一方面提供了一种包含纳米粒子的组合物，其中纳米粒子包含核苷酸或核苷酸的前药，以及药用可接受载体；其中药用可接受载体包括白蛋白。
• Chemoenzymatic Synthesis of Lysophosphatidylnucleosides
  作者：Rosa Chillemi、Domenico Russo、Sebastiano Sciuto

  DOI：10.1021/jo971826v

  日期：1998.5.1

  5'-O-Lysophosphatidylnucleosides [5'-O-(1-O-acyl-sn-glycero-3-phosphoryl)nucleosides] were obtained by a two-step chemoenzymatic synthesis. 5'-O-(sn-Glycero-3-phosphoryl)nucleosides (5'-GPNs) were first prepared from a phosphoramidite of 1,2-O-isopropylidene-sn-glycerol and appropriately protected nucleosides, applying the phosphoramidite methodology on the solid phase or in solution. In a following step, the regioselective acylation at the C-l hydroxyl of the glycerol moiety of 5'-GPNs was achieved by a lipase-catalyzed transacylation with activated fatty acid esters in organic solvent. Some deoxyribo- and ribonucleosides, as well, were converted into the corresponding lysophosphatidyl derivatives utilizing either saturated or unsaturated fatty acid esters with different length alkyl chains. The synthesis was also applied to the preparation of O-(1-O-palmitoyl-sn-glycero-3-phosphoryl) conjugates of Acyclovir and AZT, of potential pharmacological interest.