70479-46-8

Upstream product

• 367-21-5 3-chloro-4-fluorophenylamine 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 100-39-0 benzyl bromide 
• 75073-15-3 ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline 3-carboxylate 
• 70032-30-3 diethyl 2-[(3-chloro-4-fluorophenylamino)methylene]malonate 
• 100-46-9 benzylamine 
• 86483-52-5 2,4-dichloro-alpha(elhoxymethlene)-5-fluoro-beta-oxo-benzene propanoic acid ethyl ester 
• 118539-41-6 (Z)-3-Benzylamino-2-(2,4-dichloro-5-fluoro-benzoyl)-acrylic acid ethyl ester 
• 100-44-7 benzyl chloride 
• 70458-93-4 7-Chloro-6-fluoro-4-hydroxy-3-quinolinecarboxylic acid ethyl ester 

Downstream Products

• 70459-18-6 1-benzyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 74011-50-0 1-benzyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid 
• 70459-17-5 1-benzyl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 

Relevant academic research and scientific papers

Developing ciprofloxacin analogues against plant DNA gyrase: A novel herbicide mode of action

Ciprofloxacin has been shown to exhibit potent herbicidal activity through action against plant DNA gyrase, presenting a novel mode of action. Analogues of ciprofloxacin have been prepared with increased herbicidal activity and diminished antibacterial activity, compared to ciprofloxacin, as demonstrated using model systems.

MONOCARBOXYLATE TRANSPORT MODULATORS AND USES THEREOF

The invention generally relates to the field of monocarboxylate transport modulators, e.g., monocarboxylate transport inhibitors, and more particularly to new substituted-quinolone compounds, the synthesis and use of these compounds and their pharmaceutical compositions, e.g., in treating, modulating, forestalling and/or reducing physiological conditions associated with monocarboxylate transport activity such as in treating cancer and other neoplastic disorders, inflammatory diseases, disorders of abnormal tissue growth and fibrosis including cardiomyopathy, obesity, diabetes, cardiovascular diseases, tissue and organ transplant rejection, and malaria.

Rational design of partial agonists for the muscarinic M1 acetylcholine receptor

Aiming to design partial agonists for a G-protein-coupled receptor based on dynamic ligand binding, we synthesized three different series of bipharmacophoric ligands composed of the orthosteric building blocks iperoxo and 1 linked to allosteric modulators (BQCA-derived compounds, BQCAd; TBPB-derived compound, TBPBd). Their interactions were studied with the human muscarinic acetylcholine M1-receptor (hM1) with respect to receptor binding and Gq-protein signaling. Results demonstrate that iperoxo/BQCAd (2, 3) and 1/BQCAd hybrids (4) act as M1 partial agonists, whereas 1/TBPBd hybrids (5) did not activate M1-receptors. Among the iperoxo/BQCAd-hybrids, spacer length in conjunction with the pattern of substitution tuned efficacy. Most interestingly, a model of dynamic ligand binding revealed that the spacer length of 2a and 3a controlled the probability of switch between the inactive purely allosteric and the active bitopic orthosteric/allosteric binding pose. In summary, dynamic ligand binding can be exploited in M1 receptors to design partial agonists with graded efficacy.

Synthesis, characterization and pharmacological studies of some substituted fluoroquinolones

Certain N-1 substituted fluoroquinolonic derivatives were synthesized and evaluated for antimicrobial and antioxidant activities. N-1 alkyl/ aryl/ aryl sulphonyl substituted derivatives of the title compounds have been synthesized to identify newer fluoroquinolones which have better efficacy, lesser side effects and well tolerability. The biological evaluation of the synthesized fluoroquinolone derivatives was carried out using agar-well diffusion method and compounds FI-ETH, FII-SUL, FIII-ATY, FIV-BZO, and FV-BZY were found to be active against both Gram-positive and Gram-negative bacteria having activity comparable to that of standard drug i.e. Ofloxacin 10mg/ml. N-1 substituted moiety is mostly active against strain is S. aureus, K. Pneumonia, and E. coli with concentration of 100 - 150μg/ml, and less active against strain is B. subtilis. And secondly, antioxidant activity is that of show the better activity by this four method DPPH Free Radical Scavenging Assay, Hydrogen Peroxide Radical Scavenging Activity, Nitric Oxide Assay, and Reducing Power Assay. All the synthesized compounds show the better antioxidant activity and in fourth one method result is mostly capable reducing power activity of the synthesized compounds.

Synthesis of 6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives as potential antimicrobial agents

In the present study, a series of 1-ethyl/benzyl-6-fluoro-7-(substituted piperazin-1-yl)1,4-dihydro-4-oxo-quinoline-3-carboxylic acid were synthesized and characterized by IR, 1H-NMR, mass spectral and elemental analysis. The in vitro antibacterial and antifungal activities of the compounds were evaluated by paper disc diffusion method. The minimum inhibitory concentrations (MIC) of the compounds were also determined by agar streak dilution method. The in vivo antibacterial activity of the compounds against Escherichia coli was also evaluated by mouse protection test. All the compounds exhibited significant antibacterial and weak antifungal activities. The in vivo antibacterial activity (ED50) against E. coli was 50-160 mg kg -1 in the order of 7100 μg mL-1 against Staphylococcus aureus, Staphylococcus epidermidis, Micrococcus luteus, Bacillus cereus, E. coli, Klebsiella pneumoniae, Candida albicans and Aspergillus niger.

SOME REACTIONS OF N-PROPADIENYL-4-QUINOLONES

N-Alkylation of ethyl 6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (Vg) with 3-bromopropyne followed by acidic hydrolysis provided N-propynyl derivative Ic which in alkaline media yielded N-propadienyl derivative IId.Propadienyl derivatives IIa and IIb treated with primary or secondary amines provided intermediates IIIa-IIIc which were hydrolyzed to N-acetonyl derivatives IVa and IVb, respectively.N-Benzylation of ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (Va) followed by hydrolysis yielded 1-benzyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (Vd) which upon a treatment with N-methylpiperazine provided Ve.Compound Ve was hydrogenated on Pd to 6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid (Vf).

Fluoronaphthyridines and Quinolones as Antibacterial Agents. 1. Synthesis and Structure-Activity Relationships of New 1-Substituted Derivatives

A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated.These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position.As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin (1) or ciprofloxacin (10).Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.

Structure-Activity Relationships of Antibacterial 6,7- and 7,8-Disubstituted 1-Alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic Acids

Previous quantitative and qualitative structure-activity studies in antibacterial monosubstituted 1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids prompted us to synthesize the 6,7,8-polysubstituted compounds.In this paper, the preparation and antibacterial activity of the 6,7- and 7,8-disubstituted compounds and their derivatives are described.Among these compounds, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid (34) possessed many significant activities and was more active than oxolinic acid (84) against Gram-positive andGram-negative bacteria.Structure activity relationships are discussed.