1-((2R,4S,5S)-4-Acetyl-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione | 795275-16-0

• 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: 1-((2R,4S,5S)-4-Acetyl-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,4S,5S)-4-acetyl-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 795275-16-0
• 化学式: C₁₂H₁₆N₂O₅
• 分子量: 268.269
• InChiKey: XMIGGBBCHJGAIO-OPRDCNLKSA-N

物化性质

• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-((2R,4S,5S)-4-Acetyl-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 在 磷酸三甲酯 、 三氯氧磷 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 [[(2S,3S,5R)-3-acetyl-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
  参考文献：
  名称：

  Structure-based design, synthesis, and in vitro assay of novel nucleoside analog inhibitors against HIV-1 reverse transcriptase

  摘要：

  Crystal structure of HIV-RT in complex with a DNA template:primer and a dTTP leads us to design and synthesize a new class of nucleoside analog inhibitors containing a branched 3'-group against HIV-RT. An in vitro primer extension assay indicates that three out of five compounds are effective HIV-RT inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.099
• 作为产物：
  描述：

  1-(5'-O-4,4'-dimethoxytrityl-2',3'-dideoxy-3'-C-formyl-β-D-erythro-pentofuranosyl)thymine 在 cerium(III) chloride 、 戴斯-马丁氧化剂 、 三氯乙酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-((2R,4S,5S)-4-Acetyl-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Structure-based design, synthesis, and in vitro assay of novel nucleoside analog inhibitors against HIV-1 reverse transcriptase

  摘要：

  Crystal structure of HIV-RT in complex with a DNA template:primer and a dTTP leads us to design and synthesize a new class of nucleoside analog inhibitors containing a branched 3'-group against HIV-RT. An in vitro primer extension assay indicates that three out of five compounds are effective HIV-RT inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.099

文献信息

• Nucleoside analog inhibitors of reverse transcriptase
  申请人：——

  公开号：US20040235869A1

  公开（公告）日：2004-11-25

  Compounds of formula (XXIII), or pharmaceutically acceptable salts or esters thereof, are inhibitors of reverse transcriptase: 1 R 4 is a nucleoside with Q substituting a 3′ hydroxyl group, and Q is a moiety of formulas (XXIV)-(XXXII): 2

  公式（XXIII）的化合物，或其药学上可接受的盐或酯，是反转录酶的抑制剂：1R4是一种核苷，其中Q替代3'羟基，Q是公式（XXIV）-（XXXII）的一个部分。
• Structure-based design, synthesis, and in vitro assay of novel nucleoside analog inhibitors against HIV-1 reverse transcriptase
  作者：Xianjun Liu、Wei Xie、Raven H. Huang

  DOI：10.1016/j.bmcl.2005.05.099

  日期：2005.8

  Crystal structure of HIV-RT in complex with a DNA template:primer and a dTTP leads us to design and synthesize a new class of nucleoside analog inhibitors containing a branched 3'-group against HIV-RT. An in vitro primer extension assay indicates that three out of five compounds are effective HIV-RT inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.