Abstract
A new series of semicarbazone-triazole hybrid derivatives have been synthesized by condensation between heterocyclic aldehydes and the commercial semicarbazide hydrochloride. The in vitro antioxidant activity of these species was tested using 1,1-diphenyl-2-picrylhydrazyl radical, 2,2′-Azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) and Ferric reducing antioxidant power assays and their antimicrobial activity against different microbial strains was carried out. Furthermore, molecular properties prediction and drug likeness were also determinated using Molinspiration. Among such derivatives, compounds (
E
)-2-(4-((1-(2,6-dimethylphenyl)-1
H
-1,2,3-triazol-4-yl)methoxy)benzylidene)hydrazine carboxamide (
4c
), and (
E
)-2-(4-((1-(2-methoxyphenyl)-1-
H
-1,2,3-triazol-4-yl)methoxy)benzylidene)hydrazine-carboxamide (
4e
) exhibit excellent scavenging ability, especially with IC
50
= 1.57 ± 1.66 mg/mL (
4c
) and IC
50
= 1.82 ± 0.15 mg/mL (
4e
) with 1,1-diphenyl-2-picrylhydrazyl radical and IC
50
= 1.90 ± 1.33 mg/mL (
4c
) with 2,2′-Azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) as compared to the standards butylhydroxytoluene (IC
50
= 1.60 ± 1.98 mg/mL) and Trolox (IC
50
= 1.45 ± 1.33 mg/mL), respectively. The antimicrobial assay results, show that compounds
4c
and
4e
highlighted the most interesting profile with the potent activity was obtained against
S. enteritidis
(1.56-fold) and then
M. luteus
(1.45-fold) which are significantly higher than the positive control, chloramphenicol. By the other hand, the synthesized semicarbazone derivatives met the Lipinski’s rule criteria by presenting good drug likeness and bioactivity scores. The structure–property–activity relationships have been carried out in order to determine the effect of various substituents on the molecular and the biological properties. All these investigations confirm that our synthetic semicarbazone can be explored for generating new potential drug with good oral bioavailability.
Graphical abstract