1616491-55-4

Basic information

• Product Name: ethyl 1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate
• Synonyms: ethyl 1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate
• CAS NO: 1616491-55-4
• Molecular Weight: 370.337
• Mol File: 1616491-55-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: ethyl 1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate(1616491-55-4)
• EPA Substance Registry System: ethyl 1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate(1616491-55-4)

Safety Data

• Hazardous Substances Data: 1616491-55-4(Hazardous Substances Data)

Upstream product

• 103514-53-0 ethyl 6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 709-46-6 2-fluoro-5-nitrobenzoyl chloride 
• 7304-32-7 2-fluoro-5-nitrobenzoic acid 
• 1117-37-9 ethyl (E)-3-(dimethylamino)acrylate 
• 78596-42-6 ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 100-01-6 4-nitro-aniline 
• 459-46-1 4-Fluorobenzyl bromide 

Downstream Products

• 1616491-41-8 methyl 2-(3-(1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxamido)propoxy)-6-hydroxybenzoate 
• 1616491-19-0 1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1616491-20-3 6-amino-1-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 

Relevant articles and documents

Easily accessed nitroquinolones exhibiting potent and selective anti-tubercular activity

Nitro based DprE1 inhibitors exemplified by benzothiazinones have been reported to elicit potent anti-tubercular activity. Poor PK properties associated with benzothiazinones have inspired the discovery of alternative nitro based DprE1 inhibitors. Quinolone based antibiotics on the other hand have good PK properties. The potent anti-tubercular activity of nitro compounds and the good PK properties of the quinolones have elicited an interest in us to construct a new class of nitro containing compounds around the quinolone scaffold with the aim of identifying novel DprE1 inhibitors with potent anti-tubercular activity. Thus, we report herein the anti-tubercular activity of novel 6-nitroquinolone-3-carboxamide derivatives achieved using less than five cheap synthetic transformations. Among the 23 target compounds evaluated for anti-tubercular activity, 12 were active against Mtb─ exhibiting activity in the range of a molecular weight of 399 Da and ClogP value of 2.7 is the most active (MIC90: 2) and C-3 (R3) of the quinolone ring. The activity data suggest that the nature of R3 has a stronger influence on the SAR compared to R2; with a fluorobenzyl and chlorobenzyl moiety at R2 being the most favoured when R3 is an aliphatic amine. Docking study confirms that compound 25 binds to the same hydrophobic pocket as does TCA1, and other nitro based DprE1 inhibitors, with its nitro group in close proximity with Cys387 residue.

6-Nitro-1-benzylquinolones exhibiting specific antitubercular activity

In this study, we synthesized novel nitro quinolone-based compounds and tested them in vitro against a panel of Gram-positive and Gram-negative pathogens including Mycobacterium tuberculosis (MTB), Pseudomonas aeruginosa, Acinetobacter baumannii, Klebsiella pneumonia, Staphylococcus aureus, and Escherichia coli for antibacterial activities and also against HeLa cells for overt cytotoxicity. Compound 8e was identified as a non-toxic, potent hit with selective activity (MIC90???0.24?μm) against MTB. 8e, however, showed no activity against DprE1 mutant, suggesting DprE1 as the likely target for this compound class.