6-[3-(4-Ethyl-phenoxy)-propyl]-3-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3H-furo[2,3-d]pyrimidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃[2,3-d]嘧啶
• 英文名称: 6-[3-(4-Ethyl-phenoxy)-propyl]-3-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3H-furo[2,3-d]pyrimidin-2-one
• 英文别名: 6-[3-(4-ethylphenoxy)propyl]-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]furo[2,3-d]pyrimidin-2-one
• 化学式: C₂₂H₂₆N₂O₆
• 分子量: 414.458
• InChiKey: OOGZNDYBVSTYDC-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(3-chloropropoxy)-4-ethylbenzene 在 copper(l) iodide 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 6-[3-(4-Ethyl-phenoxy)-propyl]-3-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3H-furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  SYNTHESIS AND IN VITRO EVALUATION OF NOVEL ANTI-VARICELLA-ZOSTER VIRUS (VZV) NUCLEOSIDES

  摘要：

  A series of alkyl-aryl, -phenoxy, and -thiophenoxy bicyclic furo pyrimidine nucleosides have been successfully synthesised by Pd-coupling of 5-iodo-2'-deoxyuridine (IDU) with terminal alkynes, followed by in situ copper-cyclisation. Synthesised compounds (4a-i) showed an anti-VZV activity at low muM concentration, comparable to that of current treatment acyclovir.

  DOI：

  10.1081/ncn-100002343

文献信息

• SYNTHESIS AND IN VITRO EVALUATION OF NOVEL ANTI-VARICELLA-ZOSTER VIRUS (VZV) NUCLEOSIDES
  作者：Antonella Carangio、Christopher McGuigan、D. Cahard、Graciela Andrei、Robert Snoeck、Erik De Clercq、Jan Balzarini

  DOI：10.1081/ncn-100002343

  日期：2001.3.31

  A series of alkyl-aryl, -phenoxy, and -thiophenoxy bicyclic furo pyrimidine nucleosides have been successfully synthesised by Pd-coupling of 5-iodo-2'-deoxyuridine (IDU) with terminal alkynes, followed by in situ copper-cyclisation. Synthesised compounds (4a-i) showed an anti-VZV activity at low muM concentration, comparable to that of current treatment acyclovir.