1-((1R,3S)-3-Hydroxymethyl-1,3-dihydro-isobenzofuran-1-yl)-5-methyl-1H-pyrimidine-2,4-dione | 671222-99-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 1-((1R,3S)-3-Hydroxymethyl-1,3-dihydro-isobenzofuran-1-yl)-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(1R,3S)-3-(hydroxymethyl)-1,3-dihydro-2-benzofuran-1-yl]-5-methylpyrimidine-2,4-dione
• CAS: 671222-99-4
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: KXCXIHQJOSNNJW-DGCLKSJQSA-N

物化性质

• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-((1R,3S)-3-Hydroxymethyl-1,3-dihydro-isobenzofuran-1-yl)-5-methyl-1H-pyrimidine-2,4-dione 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 cis-1-(1,3-dihydro-3-hydroxymethylbenzo[c]furane) thymidin-5'-yl bis(S-pivaloyl-2-thio-ethyl)phosphate
  参考文献：
  名称：

  Synthesis, Stability, and Biological Evaluation of 1,3-Dihydrobenzo[c]furan Analogue of d4T and Its SATE Pronucleotide

  摘要：

  The anti-HIV activity and stability studies of 1,3-dihydrobenzo[c]furan analogue of d4T are reported. The corresponding mononucleoside phosphotriester derivative bearing a S-pivaloyl-2-thioethyl (tBuSATE) group, as biolabile phosphate protection, is also studied.

  DOI：

  10.1081/ncn-120022691
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 sodium hydroxide 、 四氯化锡 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 为溶剂， 生成 1-((1R,3S)-3-Hydroxymethyl-1,3-dihydro-isobenzofuran-1-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  1,3-Dihydrobenzo[ c ]furan nucleoside analogues: additional studies of the thymine derivative

  摘要：

  The detailed study of the 1,3-dihydrobenzo[c]furan derivative of thymine is reported. The lack of anti-HIV activity of this compound in cell culture experiments is shown to be related to the inability of the corresponding 5'-triphosphate derivative to interact efficiently with the reverse transcriptase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.031

文献信息

• Synthesis, Stability, and Biological Evaluation of 1,3-Dihydrobenzo[<i>c</i>]furan Analogue of d4T and Its SATE Pronucleotide
  作者：Christophe Len、Abdelmajid Selouane、Denis Postel、Pierre Villa、Anne-Marie Aubertin、David Egron、Gilles Gosselin、Christian Périgaud

  DOI：10.1081/ncn-120022691

  日期：2003.10

  The anti-HIV activity and stability studies of 1,3-dihydrobenzo[c]furan analogue of d4T are reported. The corresponding mononucleoside phosphotriester derivative bearing a S-pivaloyl-2-thioethyl (tBuSATE) group, as biolabile phosphate protection, is also studied.
• 1,3-Dihydrobenzo[ c ]furan nucleoside analogues: additional studies of the thymine derivative
  作者：David Egron、Christian Périgaud、Gilles Gosselin、Anne-Marie Aubertin、Abdesslem Faraj、Majid Sélouane、Denis Postel、Christophe Len

  DOI：10.1016/j.bmcl.2003.09.031

  日期：2003.12

  The detailed study of the 1,3-dihydrobenzo[c]furan derivative of thymine is reported. The lack of anti-HIV activity of this compound in cell culture experiments is shown to be related to the inability of the corresponding 5'-triphosphate derivative to interact efficiently with the reverse transcriptase. (C) 2003 Elsevier Ltd. All rights reserved.