5-(1-propenyl)-2'-deoxyuridine | 66270-29-9

• 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: 5-(1-propenyl)-2'-deoxyuridine
• 英文别名: trans-5-(1-propenyl)-2'-deoxyuridine；5-(1-Propenyl)-2'-deoxyuridin；trans-5-(1-Propenyl)-2'-deoxyuridin；5-propenyl-2'-deoxy-uridine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(E)-prop-1-enyl]pyrimidine-2,4-dione
• CAS: 66270-29-9
• 化学式: C₁₂H₁₆N₂O₅
• 分子量: 268.269
• InChiKey: SMBMLBOPIUXCIM-YJCWOPNRSA-N

物化性质

• 密度：
  1.468±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(1-propenyl)-2'-deoxyuridine 在 二苯甲酮 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以11%的产率得到5-(propen-1-yl)-2'-deoxyuridine
  参考文献：
  名称：

  Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity

  摘要：

  A number of structurally related 5-substituted pyrimidine 2'-deoxyribonucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.

  DOI：

  10.1021/jm00363a009
• 作为产物：
  描述：

  盐酸土霉素兽药 在 RhCl(PPh₃)3 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以29%的产率得到5-(1-propenyl)-2'-deoxyuridine
  参考文献：
  名称：

  Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity

  摘要：

  A number of structurally related 5-substituted pyrimidine 2'-deoxyribonucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.

  DOI：

  10.1021/jm00363a009

文献信息

• EP0135587A4
  申请人：——

  公开号：EP0135587A4

  公开（公告）日：1986-04-02
• DEFINED SEQUENCE SINGLE STRAND OLIGONUCLEOTIDES INCORPORATING REPORTER GROUPS, PROCESS FOR THE CHEMICAL SYNTHESIS THEREOF, AND NUCLEOSIDES USEFUL IN SUCH SYNTHESIS
  申请人：SYNGENE, INC.

  公开号：EP0135587B1

  公开（公告）日：1990-05-02
• USE OF NUCLEOSIDES FOR THE MANUFACTURE OF MEDICAMENT FOR TREATMENT OF DISEASES CAUSED BY RETROVIRUS OR HEPATITIS B VIRUS
  申请人：ASTRA LAKEMEDEL AKTIEBOLAG

  公开号：EP0294443A1

  公开（公告）日：1988-12-14
• ENGINEERED DNA FOR MOLECULAR ELECTRONICS
  申请人：Universal Sequencing Technology Corporation

  公开号：EP4061959A1

  公开（公告）日：2022-09-28
• US4247544A
  申请人：——

  公开号：US4247544A

  公开（公告）日：1981-01-27