5-ethyl-1-[(3S,5S)-5-(hydroxymethyl)-1-(4-methylphenyl)sulfonylpyrrolidin-3-yl]pyrimidine-2,4-dione | 216692-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-ethyl-1-[(3S,5S)-5-(hydroxymethyl)-1-(4-methylphenyl)sulfonylpyrrolidin-3-yl]pyrimidine-2,4-dione
• CAS: 216692-63-6
• 化学式: C₁₈H₂₃N₃O₅S
• 分子量: 393.464
• InChiKey: YSFCTACGDAUWQX-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-ethyl-1-[(3S,5S)-5-(hydroxymethyl)-1-(4-methylphenyl)sulfonylpyrrolidin-3-yl]pyrimidine-2,4-dione 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 溴 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.83h， 生成 [(2S,4S)-4-[5-[(E)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-1-(4-methylphenyl)sulfonylpyrrolidin-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis and biological properties of a new series of 5-substituted-pyrimidine-L-nucleoside analogues

  摘要：

  trans-4-hydroxy-L-proline (5) has been elaborated into a new series of pyrrolidine-L-nucleoside analogues incorporating non-standard 5-substituted-pyrimidine nucleobases, via the azidopyrrolidines 12 and 13. Those analogues employing an acyl protecting group on the primary hydroxyl functionality underwent radical bromination of the ethyl side chain of the pyrimidine ring, to provide E-5-(2-bromovinyl)uracil-pyrrolidine-L-nucleosides 23-26. Of the compounds assessed for potential antiviral activity only 5-ethyluracil-(benzoyloxymethyl)pyrrolidine 20 was found to be a specific inhibitor of vaccinia virus. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00821-7
• 作为产物：
  描述：

  L-羟基脯氨酸 在 palladium on activated charcoal 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 锂硼氢 、 氯化亚砜 、 sodium azide 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 117.0h， 生成 5-ethyl-1-[(3S,5S)-5-(hydroxymethyl)-1-(4-methylphenyl)sulfonylpyrrolidin-3-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and biological properties of a new series of 5-substituted-pyrimidine-L-nucleoside analogues

  摘要：

  trans-4-hydroxy-L-proline (5) has been elaborated into a new series of pyrrolidine-L-nucleoside analogues incorporating non-standard 5-substituted-pyrimidine nucleobases, via the azidopyrrolidines 12 and 13. Those analogues employing an acyl protecting group on the primary hydroxyl functionality underwent radical bromination of the ethyl side chain of the pyrimidine ring, to provide E-5-(2-bromovinyl)uracil-pyrrolidine-L-nucleosides 23-26. Of the compounds assessed for potential antiviral activity only 5-ethyluracil-(benzoyloxymethyl)pyrrolidine 20 was found to be a specific inhibitor of vaccinia virus. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00821-7

文献信息

• Synthesis and biological properties of a new series of 5-substituted-pyrimidine-L-nucleoside analogues
  作者：Nigel B. Westwood、Richard T. Walker

  DOI：10.1016/s0040-4020(98)00821-7

  日期：1998.10

  trans-4-hydroxy-L-proline (5) has been elaborated into a new series of pyrrolidine-L-nucleoside analogues incorporating non-standard 5-substituted-pyrimidine nucleobases, via the azidopyrrolidines 12 and 13. Those analogues employing an acyl protecting group on the primary hydroxyl functionality underwent radical bromination of the ethyl side chain of the pyrimidine ring, to provide E-5-(2-bromovinyl)uracil-pyrrolidine-L-nucleosides 23-26. Of the compounds assessed for potential antiviral activity only 5-ethyluracil-(benzoyloxymethyl)pyrrolidine 20 was found to be a specific inhibitor of vaccinia virus. (C) 1998 Elsevier Science Ltd. All rights reserved.