5-O-butyl-D-ribose | 114405-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-butyl-D-ribose
• CAS: 114405-62-8；114405-63-9
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: FSAFLROJIAFTIY-BYBOBHAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.76
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-O-butyl-D-ribose 在 吡啶 、 硫酸 、 sodium methylate 、 四氯化锡 、 magnesium sulfate 、 fluorine 、 calcium carbonate 作用下， 以 吡啶 、 甲醇 、 溶剂黄146 为溶剂， 反应 54.5h， 生成 5'-O-butyl-5-fluorouridine
  参考文献：
  名称：

  Holy, Antonin; Koenig, Joachim; Vesely, Jiri, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 6, p. 1589 - 1608

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 5-O-n-butyl-2,3-O-isopropylidene-D-ribofuranoside 在 盐酸 作用下， 反应 2.0h， 生成 5-O-butyl-D-ribose
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Certain 5‘-Modified Analogs of 2,5,6-Trichloro-1-(β-d-ribofuranosyl)benzimidazole

  摘要：

  A series of 5'-modified 2,5,6-trichlorobenzimidazole ribonucleosides has been synthesized and tested for activity against two human herpesviruses and for cytotoxicity. The 5'-methoxy, 5'-ethoxy, and 5'-butoxy analogs of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) were prepared by coupling the appropriate 5-O-alkyl-1,2,3-tri-O-acetyl-beta-D-ribose derivatives with 2,5,6-trichlorobenzimidazole followed by removal of the protecting groups. The 5'-deoxy-5'-fluoro, -5'-chloro, -5'-bromo, -5'-iodo, -5'-azido, and -5'-thiomethyl derivatives were synthesized in a similar fashion. All of these 5'-modified derivatives had significant activity against HCMV in plaque and yield reduction assays (IC50's = 0.5-14.2 mu M) but had little activity (IC50's > 100 mu M) against HSV-1. This pattern is similar to the antiviral activity profile observed for TCRB. The 5'-halogenated derivatives were more active than the other 5'-modified derivatives with antiviral activity well separated from cytotoxicity. In general, cytotoxicity of all the 5'-modified derivatives was greater in human foreskin fibroblasts (HFF cells) than in L1210 or K-B tumor cells. These results indicate that the viral target tolerates significant modifications of TCRB at the 5'-position without adversely affecting activity against HCMV, whereas the 5'-modifications increased cytotoxicity in human diploid cells.

  DOI：

  10.1021/jm9604888