1-(2-O-acetyl-3-azido-3-deoxy-5-O-p-toluoyl-β-D-ribofuranosyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | 219659-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(2-O-acetyl-3-azido-3-deoxy-5-O-p-toluoyl-β-D-ribofuranosyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• CAS: 219659-48-0
• 化学式: C₂₅H₂₀ClFN₄O₈
• 分子量: 558.907
• InChiKey: CMZQEGUIVHQJLX-OHUMZHCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  169.89
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-(2-O-acetyl-3-azido-3-deoxy-5-O-p-toluoyl-β-D-ribofuranosyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 在 氨 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以71%的产率得到1-(3-azido-3-deoxy-β-D-ribofuranosyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Quinolone Nucleosides: 6,7-Dihalo-N-β- and α-Glycosyl-l 4-dihydro-4-oxo-quinoline-3-carboxylic Acids and Derivatives. Synthesis, Antimicrobial and Antiviral Activity

  摘要：

  Reaction of the silylated 6,7-dihaloquinoline bases 10-12 with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (13) gave ethyl 7-chloro-6-flouro-1,4-dihydro-4-oxo-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)quinoline-3-carboxylate (14) and the free acids 15 and 16, respectively, which led on deblocking of the sugar moiety to the free nucleosides 17, 18 and 20, respectively. Treatment of 14 with methanolic ammonia afforded the amide derivative 19. Ribosylation of 11 with 1,2-di-O-acetyl-3-azido-3-deoxy-5-p-toluoyl-beta-D-ribofuranose (21) afforded the azido nucleoside 22, which was again converted into the free nucleoside 23. Analogously, reaction of 11 with the chloro deoxyribose derivative 24 led to a mixture of alpha / beta (2:1) anomers of 25. Deblocking and recrystallization of the product gave mainly the alpha-anomer 26. Compounds 17-19, 23 and 26 were evaluated against Escherichia coli and found inactive. Compound 16-18 and 22 were inactive aganist HIV-1 (III B) and HIV-2 (ROD) induced cytopathicity in human MT-4 lymphocyte cells.

  DOI：

  10.1080/07328319808004315
• 作为产物：
  描述：

  7-氯-6-氟-4-氧代-1H-喹啉-3-羧酸 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 1-(2-O-acetyl-3-azido-3-deoxy-5-O-p-toluoyl-β-D-ribofuranosyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Quinolone Nucleosides: 6,7-Dihalo-N-β- and α-Glycosyl-l 4-dihydro-4-oxo-quinoline-3-carboxylic Acids and Derivatives. Synthesis, Antimicrobial and Antiviral Activity

  摘要：

  Reaction of the silylated 6,7-dihaloquinoline bases 10-12 with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (13) gave ethyl 7-chloro-6-flouro-1,4-dihydro-4-oxo-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)quinoline-3-carboxylate (14) and the free acids 15 and 16, respectively, which led on deblocking of the sugar moiety to the free nucleosides 17, 18 and 20, respectively. Treatment of 14 with methanolic ammonia afforded the amide derivative 19. Ribosylation of 11 with 1,2-di-O-acetyl-3-azido-3-deoxy-5-p-toluoyl-beta-D-ribofuranose (21) afforded the azido nucleoside 22, which was again converted into the free nucleoside 23. Analogously, reaction of 11 with the chloro deoxyribose derivative 24 led to a mixture of alpha / beta (2:1) anomers of 25. Deblocking and recrystallization of the product gave mainly the alpha-anomer 26. Compounds 17-19, 23 and 26 were evaluated against Escherichia coli and found inactive. Compound 16-18 and 22 were inactive aganist HIV-1 (III B) and HIV-2 (ROD) induced cytopathicity in human MT-4 lymphocyte cells.

  DOI：

  10.1080/07328319808004315