[(2S,3S,5R)-3-amino-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl N-[2-(1H-indol-3-yl)ethyl]carbamate | 1355331-57-5

• 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)-3-amino-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl N-[2-(1H-indol-3-yl)ethyl]carbamate
• CAS: 1355331-57-5
• 化学式: C₂₁H₂₅N₅O₅
• 分子量: 427.46
• InChiKey: DFRQRAUPWLJNAQ-CGTJXYLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  齐多夫定 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 [(2S,3S,5R)-3-amino-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl N-[2-(1H-indol-3-yl)ethyl]carbamate
  参考文献：
  名称：

  Synthesis and evaluation of potential inhibitors of human and Escherichia coli histidine triad nucleotide binding proteins

  摘要：

  Based on recent substrate specificity studies, a series of ribonucleotide based esters and carbamates were synthesized and screened as inhibitors of the phosphoramidases and acyl-AMP hydrolases, Escherichia coli Histidine Triad Nucleotide Binding Protein (ecHinT) and human Histidine Triad Nucleotide Binding Protein 1 (hHint1). Using our established phosphoramidase assay, K(i) values were determined. All compounds exhibited non-competitive inhibition profiles. The carbamate based inhibitors were shown to successfully suppress the Hint1-associated phenotype in E. coli, suggesting that they are permeable intracellular inhibitors of ecHinT. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.082

文献信息

• Synthesis and evaluation of potential inhibitors of human and Escherichia coli histidine triad nucleotide binding proteins
  作者：Sanaa K. Bardaweel、Brahma Ghosh、Carston R. Wagner

  DOI：10.1016/j.bmcl.2011.10.082

  日期：2012.1

  Based on recent substrate specificity studies, a series of ribonucleotide based esters and carbamates were synthesized and screened as inhibitors of the phosphoramidases and acyl-AMP hydrolases, Escherichia coli Histidine Triad Nucleotide Binding Protein (ecHinT) and human Histidine Triad Nucleotide Binding Protein 1 (hHint1). Using our established phosphoramidase assay, K(i) values were determined. All compounds exhibited non-competitive inhibition profiles. The carbamate based inhibitors were shown to successfully suppress the Hint1-associated phenotype in E. coli, suggesting that they are permeable intracellular inhibitors of ecHinT. (C) 2011 Elsevier Ltd. All rights reserved.