112811-70-8Relevant articles and documents
Synthesis method of gatifloxacin cyclic ester
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, (2019/11/04)
The invention belongs to a production process of a pharmaceutical intermediate, and particularly discloses a synthesis method of gatifloxacin cyclic ester. The synthesis method comprises the followingsteps: performing hydrolysis, decarboxylation and methylation on 3, 4, 5, 6-tetrafluoro-N-methylphthalimide serving as a starting material to obtain 2,4,5-trifluoro-3-methoxybenzoyl chloride, coupling the 2,4,5-trifluoro-3-methoxybenzoyl chloride with N,N-ethyl dimethylaminoacrylate, then replacing with cyclopropylamine, and finally performing cyclization to produce the gatifloxacin cyclic esterunder the action of DMF and potassium fluoride. The reaction route is short, the raw materials are wide in source; furthermore, the reaction conditions are mild and easy to operate and control, whichreduces the consumption of the raw materials, facilitates the post-treatment and reduces the cost; potassium fluoride used instead of potassium carbonate in the reaction can not only reduce productionof exhaust gas, but also make the used potassium fluoride used continuously through adjustment by potassium hydroxide, and the cost is further reduced.
Synthesis and antimycobacterial evaluation of newer 1-cyclopropyl-1,4-dihydro-6-fluoro-7-(substituted secondary amino)-8-methoxy-5-(sub)-4-oxoquinoline-3-carboxylic acids
Senthilkumar, Palaniappan,Dinakaran, Murugesan,Banerjee, Debjani,Devakaram, Ruth Vandana,Yogeeswari, Perumal,China, Arnab,Nagaraja, Valakunja,Sriram, Dharmarajan
, p. 2558 - 2569 (2008/09/21)
Thirty-four newer 1-cyclopropyl-1,4-dihydro-6-fluoro-7-(substituted secondary amino)-8-methoxy-5-(sub)-4-oxoquinoline-3-carboxylic acids were synthesized from 1,2,3,4-tetrafluoro benzene and evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant M. tuberculosis (MDR-TB) and Mycobacterium smegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase. Among the synthesized compounds, 7-(1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinolin-2(1H)-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylic acid (13n) was found to be the most active compound in vitro with MIC of 0.16 and 0.33 μM against MTB and MDR-TB, respectively. In the in vivo animal model 13n decreased the bacterial load in lung and spleen tissues with 2.54 and 2.92 - log10 protections, respectively, at the dose of 50 mg/kg body weight. Compound 13n also inhibited the supercoiling activity of mycobacterial DNA gyrase with IC50 of 30.0 μg/ml.
Synthesis of new fluoroquinolones and evaluation of their in vitro activity on Toxoplasma gondii and Plasmodium spp.
Anquetin,Rouquayrol,Mahmoudi,Santillana-Hayat,Gozalbes,Greiner,Farhati,Derouin,Guedj,Vierling
, p. 2773 - 2776 (2007/10/03)
The synthesis of four new computer-designed fluoroquinolones which have been predicted by QSAR analysis to be active against the protozoa Toxoplasma gondii is described. These compounds are inhibitory in vitro for T. gondii. One of these compounds has a remarkably high activity comparable to that of trovafloxacin. It combines the basic cyclopropyl-quinoline structure of gatifloxacin or moxifloxacin with the C-7 6-amino-3-azabicyclo[3.1.0]hexyl side chain of trovafloxacin. The four compounds are also inhibitory for blood stages of Plasmodium falciparum though at high concentration. These results confirm the potential of quinolones as anti-T. gondii and antimalarial drugs but also show that the QSAR models for T. gondii cannot be reliably extended for screening antimalarial activity.
