1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylaminothiocarbonyl-hydrazinocarbonylmethyl]-1-piperazinyl)-3-quinolinecarboxylic acid | 850630-91-0

• 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-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylaminothiocarbonyl-hydrazinocarbonylmethyl]-1-piperazinyl)-3-quinolinecarboxylic acid
• 英文别名: 1-ethyl-6-fluoro-4-oxo-7-[4-[2-oxo-2-[2-[[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]carbamothioyl]hydrazinyl]ethyl]piperazin-1-yl]quinoline-3-carboxylic acid
• CAS: 850630-91-0
• 化学式: C₃₃H₄₁FN₆O₁₃S
• 分子量: 780.785
• InChiKey: GPCFJTGTYHLMGU-PLZPULBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  264
• 氢给体数：
  4
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylaminothiocarbonyl-hydrazinocarbonylmethyl]-1-piperazinyl)-3-quinolinecarboxylic acid 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以85%的产率得到1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-[β-D-galactopyranosylaminothiocarbonyl-hydrazinocarbonylmethyl]-1-piperazinyl)-3-quinolinecarboxylic acid
  参考文献：
  名称：

  New Carbohydrate Derivatives of Norfloxacin

  摘要：

  New classes of sugar derivatives of the antibacterial drug norfloxacin (1) were synthesized by substituting the N-4' of the piperazinyl moiety of the molecule. Direct coupling with gluco- and galactopyranosyl units afforded glycosylamines 2-5. Introduction of urea or thiourea linkage between glycosyl and norfloxacin units was produced with the corresponding glycosyl isocyanates or isothiocyanates. For the synthesis of unprotected sugar urea compounds, a new approach was applied by using 1,2-N, O-carbonyl-beta-D-glycopyranoses. Hydrazinocarbonyl-methyl- and -propyl spacers also were found appropriate for linking norfloxacin with sugar units.

  DOI：

  10.1081/car-200049410
• 作为产物：
  描述：

  1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-[ethoxycarbonylmethyl]-1-piperazinyl)-3-quinolinecarboxylic acid 在 一水合肼 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylaminothiocarbonyl-hydrazinocarbonylmethyl]-1-piperazinyl)-3-quinolinecarboxylic acid
  参考文献：
  名称：

  New Carbohydrate Derivatives of Norfloxacin

  摘要：

  New classes of sugar derivatives of the antibacterial drug norfloxacin (1) were synthesized by substituting the N-4' of the piperazinyl moiety of the molecule. Direct coupling with gluco- and galactopyranosyl units afforded glycosylamines 2-5. Introduction of urea or thiourea linkage between glycosyl and norfloxacin units was produced with the corresponding glycosyl isocyanates or isothiocyanates. For the synthesis of unprotected sugar urea compounds, a new approach was applied by using 1,2-N, O-carbonyl-beta-D-glycopyranoses. Hydrazinocarbonyl-methyl- and -propyl spacers also were found appropriate for linking norfloxacin with sugar units.

  DOI：

  10.1081/car-200049410