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Synthesis and SPAR exploration of new semicarbazone-triazole hybrids in search of potent antioxidant, antibacterial and antifungal agents

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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)-1H-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 IC50 = 1.57 ± 1.66 mg/mL (4c) and IC50 = 1.82 ± 0.15 mg/mL (4e) with 1,1-diphenyl-2-picrylhydrazyl radical and IC50 = 1.90 ± 1.33 mg/mL (4c) with 2,2′-Azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) as compared to the standards butylhydroxytoluene (IC50 = 1.60 ± 1.98 mg/mL) and Trolox (IC50 = 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.

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Authors and Affiliations

  1. Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Faculty of Sciences of Monastir, University of Monastir, Avenue of the Environment, Monastir, 5019, Tunisia

    Jihed Brahmi & Kaïss Aouadi

  2. Laboratory of Plant Biotechnology Applied to Crop Improvement, Faculty of Sciences of Sfax, University of Sfax, B.P. 11713000, Sfax, Tunisia

    Sana Bakari & Adel Kadri

  3. Laboratory of Physico-Chemistry of Materials, Faculty of Sciences of Monastir, University of Monastir, Avenue of the Environment, 5019, Monastir, Tunisia

    Soumaya Nasri & Habib Nasri

  4. College of Science and Arts in Baljurashi, Al Baha University, P.O. Box 1988, Al Baha, Saudi Arabia

    Adel Kadri

  5. Department of Chemistry, Qassim University-College of Science, Buraidah, 51452, Saudi Arabia

    Kaïss Aouadi

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  1. Jihed Brahmi
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  2. Sana Bakari
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  3. Soumaya Nasri
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  4. Habib Nasri
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  5. Adel Kadri
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  6. Kaïss Aouadi
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Correspondence to Kaïss Aouadi.

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Brahmi, J., Bakari, S., Nasri, S. et al. Synthesis and SPAR exploration of new semicarbazone-triazole hybrids in search of potent antioxidant, antibacterial and antifungal agents. Mol Biol Rep 46, 679–686 (2019). https://doi.org/10.1007/s11033-018-4523-y

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  • DOI: https://doi.org/10.1007/s11033-018-4523-y

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