Synthesis, antimicrobial, antioxidant, and ADMET studies of quinoline derivatives
Open Access
- 31 March 2021
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 12 (1), 37-44
- https://doi.org/10.5155/eurjchem.12.1.37-44.2038
Abstract
The synthesis, antimicrobial, and antioxidant activities of new quinoline analogs were carried out with the aim to find possible hits/leads that can be taken up for future drug development. A series of 2-amino-N’-((2-chloroquinolin-3-yl)methylene)acetohydrazide derivatives (6a-h) have been synthesized by reacting 2-chloro-N’-((2-chloroquinolin-3-yl)methylene)acetohydrazide (5a) and N’-((6-bromo-2-chloroquinolin-3-yl)methylene)-2-chloroacetohydrazide (5b) with secondary amines (Morpholine, diethylamine, piperidine and 1-methylpiperazine). The characterization was achieved by FT-IR, 1H NMR, 13C NMR, and mass spectral analysis. The in silico ADMET studies of the synthesized molecules were analyzed for their drug likeliness and toxic properties. The ADMET study indicates that the synthesized compounds were found to be possessing reliable ADME properties and are nontoxic. The antimicrobial properties were tested against bacterial and fungal species with amoxicillin and fluconazole as standard drugs. The compounds 6a, 6c, 6e, and 6g exhibited good antibacterial potency against P. aeruginosa, and the compounds 6a, 6f, and 6h have shown good activity against E. coli with 1000 µg/mL. The compounds 6b, 6c, and 6e have moderate activity against fungal species C. oxysporum and the compounds 6c, 6e, 6f, 6g, and 6h have good activity against P. chrysogenum. Synthesized compounds were also tested for the DPPH· free radical scavenging activity to check the antioxidant potential, and the results revealed that the compounds 6a, 6b, 6c, and 6e have exhibited antioxidant potency than the remaining synthesized derivatives. The possible hits generated from biological activity could be taken for the generation of lead molecules for the drug discovery of antimicrobial and antioxidant entities from quinoline.Keywords
This publication has 35 references indexed in Scilit:
- SYNTHESIS, ANTIPLASMODIAL AND ADMET STUDIES OF 4-METHYLAMINO-2-PHENYLQUINOLINE ANALOGSInternational Journal of Pharmacy and Pharmaceutical Sciences, 2016
- A new strategy to fight antimicrobial resistance: the revival of old antibioticsFrontiers in Microbiology, 2014
- Synthesis and anti-HIV activity of alkylated quinoline 2,4-diolsBioorganic & Medicinal Chemistry, 2010
- Design, synthesis, biological evaluation and molecular modelling studies of novel quinoline derivatives against Mycobacterium tuberculosisBioorganic & Medicinal Chemistry, 2009
- Synthesis and antimicrobial activity of quinoline-based 2-pyrazolinesChemical Papers, 2008
- Expeditious synthesis and cytotoxic activity of new cyanoindolo[3,2-c]quinolines and benzimidazo[1,2-c]quinazolinesBioorganic & Medicinal Chemistry Letters, 2000
- 2-substituted quinoline alkaloids as potential antileishmanial drugsAntimicrobial Agents and Chemotherapy, 1993
- Synthesis of some new quinoline derivatives - potential antimalarial drugsPure and Applied Chemistry, 1990
- Potential antitumor agents. 57. 2-Phenylquinoline-8-carboxamides as minimal DNA-intercalating antitumor agents with in vivo solid tumor activityJournal of Medicinal Chemistry, 1989
- Antimalarials.1 α-Alkyl and Dialkylaminomethyl-2-phenyl-4-quinolinemethanolsJournal of the American Chemical Society, 1946