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112811-71-9Relevant academic research and scientific papers
COMPOUNDS TARGETING RNA-BINDING PROTEINS OR RNA-MODIFYING PROTEINS
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, (2021/09/11)
The invention relates to a compound represented by Formula (I): or a pharmaceutically acceptable salt thereof, compositions comprising the same and methods of preparing and using the same. The variables are described herein.
Preparation method of 1-cyclopropyl-6,7-difluoro-8-methoxyfluoroquinolone-3-carboxylate
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, (2020/06/17)
The invention discloses a preparation method of 1-cyclopropyl-6,7-difluoro-8-methoxyfluoroquinolone-3-carboxylate, wherein the 1-cyclopropyl-6,7-difluoro-8-methoxyfluoroquinolone-3-carboxylate is prepared by taking 2-(2,3,4,5-tetrafluorophenyl)formyl-3-(N,N-dimethylamino)acrylate prepared from cheap and easily available 2,3,4,5-tetrafluorobenzoyl chloride as a raw material through substitution, secondary ring closing, hydrolysis and secondary substitution reaction. The preparation method has the advantages of environmental protection, no pollution, easily available raw materials, wide raw material source, low cost and simple method, is suitable for industrial production, and solves the problems that in the prior art, the preparation cost is high, and industrial production is difficult.
Gatifloxacin and synthesis method thereof
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Paragraph 0061-0062; 0065-0066; 0069-0070, (2020/03/23)
The invention relates to a gatifloxacin and a synthesis method thereof. The synthesis method comprises the following steps: uniformly mixing N,N-dimethylaminoethyl acrylate, 2,4,5-trifluoro-3-methoxybenzoylchloride, ethyl acetate and triethylamine, and carrying out a complete reaction so as to obtain a first intermediate; uniformly mixing the first intermediate with acetic acid and cyclopropylamine, and carrying out a complete reaction to obtain a second intermediate; uniformly mixing the second intermediate with a strong base, and carrying out a complete reaction to obtain gatifloxacin cyclization ester; carrying out an ester exchange reaction on the gatifloxacin cycliztion ester to so as to obtain a third intermediate; uniformly mixing the third intermediate with 2-methylpiperazine, carrying out a complete reaction, and hydrolyzing and acidifying the obtained reaction product to obtain the gatifloxacin, wherein the strong base is selected from at least one of sodium hydroxide and potassium hydroxide. The synthesis method of gatifloxacin adopts the sodium hydroxide and potassium hydroxide to carry out the cyclization reaction, so that the cyclization reaction time is greatly shortened, and the time cost for synthesizing gatifloxacin is reduced.
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.
Novel fluoroquinolones and use thereof to treat bacterial infections
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, (2016/01/12)
The present invention relates to novel fluoroquinolones possessing a piperazine moiety substituted by a long alkyl chain, pharmaceutical compositions or medicament containing them and use thereof to treat bacterial infection.
Synthesis of gatifloxacin derivatives and their biological activities against Mycobacterium leprae and Mycobacterium tuberculosis
Gomez, Catherine,Ponien, Prishila,Serradji, Nawal,Lamouri, Aazdine,Pantel, Alix,Capton, Estelle,Jarlier, Vincent,Anquetin, Guillaume,Aubry, Alexandra
, p. 948 - 956 (2013/03/13)
Novel 3′-piperazinyl derivatives of the 8-hydrogeno and 8-methoxy-6-fluoro-1-cyclopropyl-4-quinolone-3-carboxylic acid scaffolds were designed, synthesized and characterized by 1H, 13C and 19F NMR, and HRMS. The activity of these derivatives against pathogenic mycobacteria (M. leprae and M. tuberculosis), wild-type (WT) strains or strains harboring mutations implicated in quinolone resistance, were determined by measuring drug concentrations inhibiting cell growth (MIC) and/or DNA supercoiling by DNA gyrase (IC50), or inducing 25% DNA cleavage by DNA gyrase (CC25). Compound 4 (with a methoxy in R8 and a secondary carbamate in R3′) and compound 5 (with a hydrogen in R8 and an ethyl ester in R3′) displayed biological activities close to those of ofloxacin but inferior to those of gatifloxacin and moxifloxacin against M. tuberculosis and M. leprae WT DNA gyrases, whereas all of the compounds were less active in inhibiting M. tuberculosis growth and M. leprae mutant DNA gyrases. Since R3′ substitutions have been poorly investigated previously, our results may help to design new quinolone derivatives in the future.
SUBSTITUTED QUINOLONES III
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Page/Page column 15, (2009/07/25)
The invention relates to substituted quinolones and to methods for their preparation as well as to their use for the production of medicaments for the treatment and/or prophylaxis of diseases, especially for use as antiviral agents, particularly against cytomegaloviruses.
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.
Design, synthesis and activity against Toxoplasma gondii, Plasmodium spp., and Mycobacterium tuberculosis of new 6-fluoroquinolones
Anquetin, Guillaume,Greiner, Jacques,Mahmoudi, Nassira,Santillana-Hayat, Maud,Gozalbes, Rafael,Farhati, Khemais,Derouin, Francis,Aubry, Alexandra,Cambau, Emmanuelle,Vierling, Pierre
, p. 1478 - 1493 (2007/10/03)
This paper reports on the rational design of a series of new 6-fluoroquinolones by QSAR analysis against Toxoplasma (T.) gondii, their synthesis, their biological evaluation against T. gondii and Plasmodium (P.) spp., and their effect on Mycobacterium (M.) tuberculosis DNA gyrase and growth inhibition. Of the 12 computer-designed 8-ethyl(or methoxy)- and 5-ethyl-8-methoxy-6-fluoroquinolones predicted to be active against T. gondii, we succeeded in the synthesis of four 6-fluoro-8-methoxy-quinolones. The four 6-fluoro-8-methoxy-quinolones are active on T. gondii but only one is as active as predicted. One of these four compounds appears to be an antiparasitical drug of great potential with inhibitory activities comparable to or higher than that of trovafloxacin, gatifloxacin, and moxifloxacin. They also inhibit DNA supercoiling by M. tuberculosis gyrase with an efficiency comparable to that of the most active quinolones but are poor inhibitors of M. tuberculosis growth.
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.
