Design, synthesis and biological evaluation of quinoxaline N-propionic and O-propionic hydrazide derivatives as antibacterial and antifungal agents

Novel series of quinaxoline derivatives incorporating N -propionic and O -propionic hydrazide moieties were synthesized. Alkylation of 3-methylquinoxalin-2(1 H )-one with ethyl 2-bromopropanoate afforded a mixture of O -alkylated and N -alkylated 3-methylquinoxaline. Hydrazide derivatives were affor...

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Bibliographic Details
Published in:Medicinal chemistry research 2018-10, Vol.27 (10), p.2287-2296
Main Authors: El Shehry, Mohamed F., Abbas, Samir Y., Farrag, Amel M., Eissa, Sally I., Fouad, Sawsan A., Ammar, Yousry A.
Format: Article
Language:English
Subjects:
Aldehydes
Alkylation
Amphotericin B
Ampicillin
Antibacterial materials
Antifungal activity
Antifungal agents
Antimicrobial activity
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Derivatives
Fungi
Fungicides
Gentamicin
Hydrazine
Hydrazines
Hydrazones
Original Research
Pharmacology/Toxicology
Pyrazole
Quinoxaline
Synthesis
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Summary:Novel series of quinaxoline derivatives incorporating N -propionic and O -propionic hydrazide moieties were synthesized. Alkylation of 3-methylquinoxalin-2(1 H )-one with ethyl 2-bromopropanoate afforded a mixture of O -alkylated and N -alkylated 3-methylquinoxaline. Hydrazide derivatives were afforded by reaction of O -alkylated and N -alkylated 3-methylquinoxaline with hydrazine hydrate. Condensation of hydrazide derivatives with different aromatic aldehydes and formylpyrazoles afforded the corresponding hydrazone derivatives. The synthesized quinaxoline derivatives were evaluated for their expected antimicrobial activity; where, the majority of these compounds showed potent antibacterial and antifungal activities against the tested strains of bacteria and fungi. Hydrazone derivative which contain 3- p -tolyl-pyrazolyl moiety showed fourfold potency of amphotericin B in inhibiting the growth of Aspergillus fumigatus , twofold potency of gentamycin in inhibiting the growth of Neisseria gonorrhoeae , equipotent potency of ampicillin in inhibiting the growth of Streptococcus pyogenes , equipotent potency of gentamycin in inhibiting the growth of Proteus vulgaris and Shigella flexneri , equipotent potency of amphotericin B in inhibiting the growth of Aspergillus clavatus , Geotrichum candidum and Penicillium marneffei . Thus, these studies suggested that quinaxoline derivatives bearing a pyrazole moiety are interesting scaffolds for the development of novel antibacterial and antifungal agents.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-018-2235-4