3-(2'-deoxy-β-D-ribofuranosyl)-6-(4-ethoxyphenyl)-2,3-dihydrofuro-[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: 3-(2'-deoxy-β-D-ribofuranosyl)-6-(4-ethoxyphenyl)-2,3-dihydrofuro-[2,3-d]pyrimidin-2-one
• 英文别名: 6-(4-Ethoxy-phenyl)-3-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3H-furo[2,3-d]pyrimidin-2-one；6-(4-ethoxyphenyl)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]furo[2,3-d]pyrimidin-2-one
• 化学式: C₁₉H₂₀N₂O₆
• 分子量: 372.378
• InChiKey: YPJFQYWFMIPWBZ-USXIJHARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  碘苷 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 3-(2'-deoxy-β-D-ribofuranosyl)-6-(4-ethoxyphenyl)-2,3-dihydrofuro-[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  BICYCLIC FURO PYRIMIDINE NUCLEOSIDES WITH ARYLOXYPHENYL AND HALOPHENYL SUBSTITUTED SIDE CHAINS AS POTENT AND SELECTIVE VARICELLA-ZOSTER VIRUS INHIBITORS

  摘要：

  The discovery of potent and selective inhibitors of VZV based on unusual bicyclic alkyl furo pyrimidine nucleosides has been recently reported. Modifications to the side-chain by addition of a phenyl group were found to further enhance the antiviral potency of these compounds. A series of alkoxyphenyl compounds (5a-5g) and two halophenyl derivatives (5h and 5i) were successfully synthesised and displayed anti-VZV activity at low muM concentrations.

  DOI：

  10.1081/ncn-100002492

文献信息

• ANTI-VIRAL PYRIMIDINE NUCLEOSIDE ANALOGUES
  申请人：MCGUIGAN Christopher

  公开号：US20110015147A1

  公开（公告）日：2011-01-20

  A compound of formula (I) wherein Ar can be one six-membered or two fused six-membered aromatic rings; R 8 and R 9 can be hydrogen, alkyl, cycloalkyl, halogens, amino, alkylamino, dialkylamino, nitro, cyano, alkyoxy, aryloxy, thiol, alkylthiol, arythiol, or aryl; Q can be O, S or CY 2 , where Y may be H, alkyl or halogens; X can be O, NH, S, N-alkyl, (CHR 2 ) m where m is 1 to 10, and CY 2 ; Z can be O, S, NH, or N-alkyl; U″ is H and U′ can be H or CH 2 ; wherein: T can be OH, H, halogens, O-alkyl, O-acyl, O-aryl, CN, NH 2 . or N 3 ; T′ and T″ can be H or halogen; and W can be H or a phosphate group. Compounds show anti-viral activity, for example with respect to varicella zoster virus.
• Anti-Viral Pyrimidine Nucleoside Analogues
  申请人：University College Cardiff Consultants Limited

  公开号：US20140011764A1

  公开（公告）日：2014-01-09

  A compound of formula (I) wherein Ar can be one six-membered or two fused six-membered aromatic rings; R 8 and R 9 can be hydrogen, alkyl, cycloalkyl, halogen, amino, alkylamino, dialkylamino, nitro, cyano, alkyoxy, aryloxy, thiol, alkylthiol, arythiol, or aryl; Q can be O, S or CY 2 , where Y may be H, alkyl or halogen; X can be O, NH, S, N-alkyl, (CHR 2 ) m where m is 1 to 10, and CY 2 ; Z can be O, S, NH, or N-alkyl; U″ is H and U′ can be H or CH 2; wherein: T can be OH, H, halogen, O-alkyl, O-acyl, O-aryl, CN, NH 2 or N 3 ; T′ and T″ can be H or halogen; and W can be H or a phosphate group. Compounds show anti-viral activity, for example with respect to varicella zoster virus.
• US7820631B2
  申请人：——

  公开号：US7820631B2

  公开（公告）日：2010-10-26
• US8551965B2
  申请人：——

  公开号：US8551965B2

  公开（公告）日：2013-10-08
• US9351970B2
  申请人：——

  公开号：US9351970B2

  公开（公告）日：2016-05-31