98349-25-8

Basic information

• Product Name: ETHYL 1-CYCLOPROPYL-6,7-DIFLUORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE
• Synonyms: ETHYL 1-CYCLOPROPYL-6,7-DIFLUORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE;3-Quinolinecarboxylic acid, 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-, ethyl ester;Ethyl 1-Cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate
• CAS NO: 98349-25-8
• Molecular Formula: C₁₅H₁₃F₂NO₃
• Molecular Weight: 293.27
• Mol File: 98349-25-8.mol

Chemical Properties

• Melting Point: 229-230℃ (ethyl acetate )
• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: ETHYL 1-CYCLOPROPYL-6,7-DIFLUORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 1-CYCLOPROPYL-6,7-DIFLUORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE(98349-25-8)
• EPA Substance Registry System: ETHYL 1-CYCLOPROPYL-6,7-DIFLUORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE(98349-25-8)

Safety Data

• Hazardous Substances Data: 98349-25-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 1-CYCLOPROPYL-6,7-DIFLUORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE is used as an antibacterial agent for the treatment of infections caused by Mycobacterium leprae and tuberculosis. Its unique structure and potent biological activities make it a promising candidate for the development of new drugs to combat these challenging bacterial infections.
Used in Research and Development:
In addition to its potential therapeutic applications, ETHYL 1-CYCLOPROPYL-6,7-DIFLUORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE is also used in research and development for the study of its mechanism of action, optimization of its chemical structure, and evaluation of its potential synergistic effects with other drugs. This research can lead to the discovery of new and more effective treatments for various bacterial infections.

Upstream product

• 101799-75-1 α-(ethoxymethylene)-2,4,5-trifluoro-β-oxobenzenepropanoic acid, ethyl ester 
• 64-17-5 ethanol 
• 93107-30-3 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 623-47-2 propynoic acid ethyl ester 
• 88419-56-1 2,4,5-trifluorobenzoyl chloride 
• 96568-08-0 Ethyl 3-(Cyclopropylamino)-2-propenoate 
• 40648-44-0 β-ethoxyacrylic acid ethyl ester 
• 138998-46-6 ethyl 3-(dimethylamino)-2-(2,4,5-trifluorobenzoyl)prop-2-enoate 
• 13894-28-5 ethyl 3-(diethylamino)acrylate 
• 765-30-0 Cyclopropylamine 
• 924-99-2 ethyl 3-(dimethylamino)acrylate 
• 1364518-39-7 C₁₆H₁₈F₃NO₃ 
• 446-17-3 2,4,5-trifluorobenzoic acid 
• 104600-15-9 (2,4,5-trifluorobenzoyl)propanedioic acid, diethyl ester 

Downstream Products

• 105404-65-7 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate ethyl ester 
• 1429439-97-3 1-cyclopropyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinolin-3-carboxylic acid 
• 1429440-04-9 4-methoxybenzyl 5-chloro-1-cyclopropyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinolin-3-carboxylate 
• 1429440-05-0 5-chloro-1-cyclopropyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 85721-33-1 ciprofloxacin 
• 1429439-96-2 4-methoxybenzyl 1-cyclopropyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinolin-3-carboxylate 
• 1416988-36-7 1-cyclopropyl-6-fluoro-7-{4-[(4-fluoro-benzylamino)-methyl]-[1,2,3]triazol-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 1416988-35-6 7-[4-(benzylamino-methyl)-[1,2,3]triazol-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 1416988-34-5 1-cyclopropyl-6-fluoro-4-oxo-7-[4-(p-tolylamino-methyl)-[1,2,3]triazol-1-yl]-1,4-dihydro-quinoline-3-carboxylic acid 
• 1416988-33-4 1-cyclopropyl-6-fluoro-7-{4-[(4-methoxy-phenylamino)-methyl]-[1,2,3]triazol-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 

Relevant articles and documents

Synthesis of Novel Ciprofloxacin-Based Hybrid Molecules toward Potent Antimalarial Activity

Antimalarial drug resistance is a serious obstacle in the persistent quest to eradicate malaria. There is a need for potent chemical agents that are able to act on drug-resistant Plasmodium falciparum populations at reasonable concentrations without any related toxicity to the host. By rational drug design, we envisaged to address this issue by generating a novel hybrid drug possessing two pharmacophores that can act on two unique and independent targets within the cell. We synthesized a new class of ciprofloxacin-based hybrid molecules, which have been integrated with acridine, quinolone, sulphonamide, and cinnamoyl pharmacophores (1-4). We realized a potent chloroquinolone-ciprofloxacin-based antimalarial hybrid (2, CQ-CFX) whose mechanism of action is unlike that of its parent molecules indicating a unique biological target. CQ-CFX is not only potent against CQ-resistant and susceptible strains of Plasmodium falciparum at low nanomolar concentrations (IC50 values are 63.17 ± 1.2 nM and 25.52 ± 4.45 nM, respectively) but is also not toxic to mammalian and bacterial systems up to 20 μM and 1 μM, respectively.

NEXT-GENERATION MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)

The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.

A Consolidated and Continuous Synthesis of Ciprofloxacin from a Vinylogous Cyclopropyl Amide

Ciprofloxacin is a broad-spectrum antibiotic that is recognized as one of the World Health Organization's Essential Medicines. It is particularly effective in the treatment of Gram-negative bacterial infections associated with urinary, respiratory, and gastrointestinal tract infections. A streamlined and high yielding continuous synthesis of ciprofloxacin has been developed, which employs a chemoselective C-acylation step that precludes the need for intermediate isolations, extractions, or purifications. The end-to-end process has a residence time of 4.7 min with a 15.8 g/h throughput at laboratory scale and an overall isolated yield of 83%.

STREAMLINED SYNTHESES OF FLUOROQUINOLONES

Methods of synthesizing fluoroquinolones such as ciprofloxacin are provided. The methods utilize affordable materials, reduce the number of synthesis steps and provide high yields.

ANTIBIOTIC RESISTANCE BREAKERS

The invention relates to antibiotic compounds of formula (A1) and pharmaceutically acceptable salts, solvates, tautomers and combinations thereof, wherein X and L are optional linkers and one of RA or R1 comprises Ar1, wherein Ar1 is an antibiotic resistance breaker moiety which comprises an optionally substituted C6-10 aryl, C7-13 aralkyl, C5-10 heteroaryl, C6-13 heteroaralkyl, C5-10 heterocyclyl, C6-13 heterocyclalkyl, C3-10 carbocyclyl, C4-13 carbocyclalkyl, -C(=NR')-NR'R'' or –CH2- CH=CH2 group; wherein after administration of the compound to a bacterial infection this moiety reduces or prevents efflux. The invention also discloses pharmaceutical compositions comprising compounds of formula (A1) and the use of such compounds as medicaments, in particular, to treat bacterial infections, such as drug-resistant bacterial infections.

Method for efficiently and environmentally friendly preparing quinolones

The invention discloses a method for efficiently and environmentally friendly preparing quinolones. Fluorobenzoylacetic acid ethyl ester, triethyl orthoformate and amine compounds are used as raw materials, and the quinolones are synthesized by maintainin

Advantageous Use of Ionic Liquids for the Synthesis of Pharmaceutically Relevant Quinolones

The advantageous use of ionic liquids (ILs) as alternatives to common DMF as solvent in the Grohe cycloaracylation for the synthesis of pharmaceutically relevant quinolones is reported. ILs showed in many cases shorter reaction times and higher yields, complete conversions of the reactants and easy work-up procedures compared with DMF. Of the ILs screened, tributylmethylammonium methanesulfonate ([TBMA][MsO]) was selected as the most suitable for further studies. Interestingly, a wide substrate scope was observed and the IL was recycled by a green process. A further step forward in the use of [TBMA][MsO] for quinolone synthesis was the preparation by a one-pot/three-step procedure of the representative 3-carboxy-4-quinolone acid 16, which was obtained in high yield in a short time. The greener properties of ILs in comparison with DMF and their non-volatility appoint this method as a potentially efficient and alternative approach to the industrial production of quinolones.

A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow

Within a total residence time of 9 min, the sodium salt of ciprofloxacin was prepared from simple building blocks via a linear sequence of six chemical reactions in five flow reactors. Sequential offline acidifications and filtrations afforded ciprofloxacin and ciprofloxacin hydrochloride. The overall yield of the eight-step sequence was 60 %. No separation of intermediates was required throughout the synthesis when a single acylation reaction was applied to remove the main byproduct, dimethylamine.

Novel fluoroquinolones and use thereof to treat bacterial infections

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

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.