33331-59-8

Basic information

• Product Name: ethyl 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate
• Synonyms: ethyl 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate;1,4-Dihydro-1-ethyl-4-oxo-7-methyl-1,8-naphthyridine-3-carboxylic acid ethyl ester;1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester;1-Ethyl-4-oxo-7-methyl-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid ethyl ester;Nalidixic acid ethyl ester
• CAS NO: 33331-59-8
• Molecular Formula: C₁₄H₁₆N₂O₃
• Molecular Weight: 260.28844
• EINECS: 251-460-6
• Mol File: 33331-59-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 403.3°Cat760mmHg
• Flash Point: 197.7°C
• Appearance: /
• Density: 1.203g/cm³
• Vapor Pressure: 1.03E-06mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: ethyl 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate(33331-59-8)
• EPA Substance Registry System: ethyl 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate(33331-59-8)

Safety Data

• Hazardous Substances Data: 33331-59-8(Hazardous Substances Data)

Usage

General Description

Ethyl 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate is a synthetic organic compound belonging to the class of naphthyridine derivatives. It has a complex chemical structure and is commonly used in the pharmaceutical industry as a building block for the synthesis of various drugs, particularly those with antimicrobial and anti-inflammatory properties. ethyl 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate may be used as a precursor in the development of drugs for the treatment of bacterial and fungal infections or inflammatory conditions. Additionally, it has the potential to exhibit other biological activities due to its unique structure, making it an important chemical compound for research and drug discovery.

InChI:InChI=1/C14H16N2O3/c1-4-16-8-11(14(18)19-5-2)12(17)10-7-6-9(3)15-13(10)16/h6-8H,4-5H2,1-3H3

Upstream product

• 64-17-5 ethanol 
• 3374-05-8 nalidixic acid, sodium salt 
• 389-08-2 nalidixic Acid 
• 1167438-08-5 C₇₁H₉₂N₆O₁₅ 
• 33331-58-7 ethyl 4-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 13250-95-8 diethyl 2-{[(6-methyl-2-pyridyl)amino]methylene}propane-1,3-dioate 
• 1824-81-3 2-Amino-6-methylpyridine 
• 13250-96-9 ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate 
• 35482-56-5 ethyl 7-methyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 
• 78-40-0 triethyl phosphate 
• 64-67-5 diethyl sulfate 

Downstream Products

• 389-08-2 nalidixic Acid 
• 52377-28-3 nalidixic acid chloride 

Relevant articles and documents

Synthesis and biological evaluation of the thionated antibacterial agent nalidixic acid and its organoruthenium(II) complex

The thionated derivative of the antibacterial agent nalidixic acid and its organoruthenium complex were prepared, and their crystal structures were determined. The aqueous stability of the complex was studied and, unlike the case for the nalidixicato complex, increased stability of the ruthenium complex in aqueous solution was observed with only a minor degree of thionalidixicato ligand dissociated within 1 week. While the derivatization caused the antibacterial activity of the ligand against E. coli to decrease, the cytotoxicity of the complex against three cancer cell lines was significantly increased and the inhibitory potency against two enzymes of the cathepsin family was increased by 10-fold.

Re-engineering nalidixic acid's chemical scaffold: A step towards the development of novel anti-tubercular and anti-bacterial leads for resistant pathogens

Occurrence of antibacterial and antimycobacterial resistance stimulated a thrust to discover new drugs for infectious diseases. Herein we report the work on re-engineering nalidixic acid's chemical scaffold for newer leads. Stepwise clubbing of quinoxaline, 1,2,4-triazole/1,3,4-oxadiazole with nalidixic acid yielded better compounds. Compounds were screened against ciprofloxacin resistant bacteria and Mycobacterium tuberculosis H37Rv species. Results were obtained as minimum inhibitory concentration, it was evident that molecule with quinoxaline linked azide as side chain served as antitubercular lead (6.25 μg/ml) whilst molecule with oxadiazole or triazole linked quinoxaline side chain served as anti-bacterial lead. Few compounds were significantly active against Escherichia coli and Proteus vulgaris with MIC less than 0.06 μg/ml and relatively potent than ciprofloxacin. No true compound was potentially active against Salmonella species as compared to amoxicillin.

Towards calixarene-based prodrugs: Drug release and antibacterial behaviour of a water-soluble nalidixic acid/calix[4]arene ester adduct

A water-soluble calixarene-based heterocyclic podand incorporating a quinolone antibiotic subunit, the nalidixic acid, was synthesised and fully characterised. Its prodrug behaviour was assessed in vitro by HPLC, demonstrating the release of the tethered