ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-<2,3,5-tri-O-benzoyl-β-D-ribofuranosyl>quinoline-3-carboxylate | 149540-60-3

• 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: ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-<2,3,5-tri-O-benzoyl-β-D-ribofuranosyl>quinoline-3-carboxylate
• 英文别名: ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)quinoline-3-carboxylate；ethyl 7-chloro-1-[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)oxolan-2-yl]-6-fluoro-4-oxoquinoline-3-carboxylate
• CAS: 149540-60-3
• 化学式: C₃₈H₂₉ClFNO₁₀
• 分子量: 714.1
• InChiKey: DARZJZJRPFCYEL-DWNQJFHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-<2,3,5-tri-O-benzoyl-β-D-ribofuranosyl>quinoline-3-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 120.0h， 以80%的产率得到ammonium 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-(β-D-riboburanosyl)quinoline-3-carboxylate
  参考文献：
  名称：

  Cruz, Angeles de la; Elguero, Jose; Goya, Pilar, Journal of the Chemical Society. Perkin transactions I, 1993, # 7, p. 845 - 850

  摘要：

  DOI：
• 作为产物：
  描述：

  7-氯-6-氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 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 8.5h， 生成 ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-<2,3,5-tri-O-benzoyl-β-D-ribofuranosyl>quinoline-3-carboxylate
  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

文献信息

• Cruz, Angeles de la; Elguero, Jose; Goya, Pilar, Journal of the Chemical Society. Perkin transactions I, 1993, # 7, p. 845 - 850
  作者：Cruz, Angeles de la、Elguero, Jose、Goya, Pilar、Martinez, Ana、Clercq, Erik De

  DOI：——

  日期：——
• 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
  作者：Najim A. Al-Masoudi、Yaseen A. Al-Soud、Micheal Ehrmann、Erik de Clercq

  DOI：10.1080/07328319808004315

  日期：1998.12

  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.