1-ethyl-6-fluoro-4-oxo-7-(4-tritylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid | 732946-24-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-ethyl-6-fluoro-4-oxo-7-(4-tritylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(triphenylmethyl)-1-piperazinyl]-3-quinolinecarboxylic acid；1-ethyl-6-fluoro-4-oxo-7-(4-tritylpiperazin-1-yl)quinoline-3-carboxylic acid
• CAS: 732946-24-6
• 化学式: C₃₅H₃₂FN₃O₃
• 分子量: 561.656
• InChiKey: DYOYAGSORFVHKO-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  乙醇 、 1-ethyl-6-fluoro-4-oxo-7-(4-tritylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 以65 %的产率得到ethyl 1-ethyl-6-fluoro-4-oxo-7-(4-tritylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis of Novel Artemisinin, Ciprofloxacin, and Norfloxacin Hybrids with Potent Antiplasmodial Activity

  摘要：

  The synthesis and antiplasmodial evaluation of new hybrids combining the pharmacophore structures of artemisinin, ciprofloxacin or norfloxacin, and 7-chloroquinoline are reported in this study. The first step for all of the syntheses is the obtainment of key piperazine esters intermediates bearing the drugs ciprofloxacin and norfloxacin. Using these platforms, 18 final compounds were synthesized through a multistep procedure with overall yields ranging between 8 and 20%. All compounds were screened for their antiplasmodial activity against the chloroquine-resistant Plasmodium falciparum FcB1 strain. Compounds 20, 21, 22, and 28, bearing an artesunate fragment with ciprofloxacin, exhibited IC50 values in the range of 3.5–5.4 nM and excellent selectivity indices. Among the compounds bearing the artesunate moiety on the norfloxacin, two of them, 23 and 24, afforded IC50 values of 1.5 nM and 1.9 nM, respectively. They also showed excellent selectivity indices. The most potent compounds were also evaluated against the CQ-resistant Dd2 strain of Plasmodium falciparum, demonstrating that those compounds incorporating the artesunate fragment were the most potent. Finally, the combination of artesunate with either ciprofloxacin or norfloxacin moieties in a single molecular entity proved to substantially enhance the activity and selectivity when compared to the administration of the unconjugated counterparts artesunate/ciprofloxacin and artesunate/norfloxacin.

  DOI：

  10.3390/antibiotics13020142