(2S,3S,5R)-2-Hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carboxylic acid | 795275-12-6

• 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: (2S,3S,5R)-2-Hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carboxylic acid
• 英文别名: (2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-3-carboxylic acid
• CAS: 795275-12-6
• 化学式: C₁₁H₁₄N₂O₆
• 分子量: 270.242
• InChiKey: JUDQVDAYUZPJOY-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R)-2-Hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carboxylic acid 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)-2-[[hydroxy-[hydroxy(phosphonooxy)phosphoryl]oxy-phosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-3-carboxylic acid
  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 氢氧化钾 、 碘 、 三氯乙酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.17h， 生成 (2S,3S,5R)-2-Hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carboxylic acid
  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

• 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.