Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl/Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules as Antioxidant and Antibacterial Agents

Fevzi Aytemiz; Haydar Yüksek

doi:10.17798/bitlisfen.1655093

Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl/Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules as Antioxidant and Antibacterial Agents

Abstract

In this study, a total of nine new 2-[(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)azomethine]phenyl 2,5-dichlorobenzenesulfonates (4a-i) were synthesized through the reactions of 2-formylphenyl 2,5-dichlorobenzenesulfonate (3) with 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2a-i). The compounds 4a, 4e, 4g and 4h were successfully synthesized with yields exceeding 90%. Compounds 4a-i were elucidated using 1H, 13C NMR and IR spectroscopic methods. The spectroscopic data were compared with the literature, and the results were found to be consistent. The antioxidant effects of compounds 4a–i were investigated using three different methods, and it was found that compounds 4a-i showed metal chelation activity close to that of α-tocopherol, which was used as the standard. Additionally, the antimicrobial properties of the compounds 4a–i were evaluated using the agar well diffusion method against six different bacterial strains. The antimicrobial properties of the new compounds (4a-i) were compared with those of standard antibiotics such as neomycin, streptomycin, and ampicillin. It was observed that compound 4a exhibited better antimicrobial activity than neomycin and streptomycin, and comparable activity to ampicillin.

Keywords

Supporting Institution

Kafkas University Scientific Research Projects Coordination Unit

Project Number

2019-FM-09

Ethical Statement

The study is complied with research and publication ethics.

Thanks

This study was supported by Kafkas University Scientific Research Projects Coordination Unit (Doctoral Thesis Project, Project Number: 2019-FM-09).

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Details

Primary Language

English

Subjects

Organic Chemical Synthesis, Biologically Active Molecules

Journal Section

Research Article

Authors

Fevzi Aytemiz ^*
0000-0002-5982-9038
Türkiye

Haydar Yüksek
0000-0003-1289-1800
Türkiye

Publication Date

September 30, 2025

Submission Date

March 10, 2025

Acceptance Date

September 20, 2025

Published in Issue

Year 2025 Volume: 14 Number: 3

DOI

https://doi.org/10.17798/bitlisfen.1655093

IZ

https://izlik.org/JA47AH57ZN

Cite

RIS / Bibtex

APA

Aytemiz, F., & Yüksek, H. (2025). Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl/Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules as Antioxidant and Antibacterial Agents. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, 14(3), 1453-1468. https://doi.org/10.17798/bitlisfen.1655093

AMA

1.Aytemiz F, Yüksek H. Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl/Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules as Antioxidant and Antibacterial Agents. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi. 2025;14(3):1453-1468. doi:10.17798/bitlisfen.1655093

Chicago

Aytemiz, Fevzi, and Haydar Yüksek. 2025. “Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules As Antioxidant and Antibacterial Agents”. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi 14 (3): 1453-68. https://doi.org/10.17798/bitlisfen.1655093.

EndNote

Aytemiz F, Yüksek H (September 1, 2025) Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl/Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules as Antioxidant and Antibacterial Agents. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi 14 3 1453–1468.

IEEE

[1]F. Aytemiz and H. Yüksek, “Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl/Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules as Antioxidant and Antibacterial Agents”, Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, vol. 14, no. 3, pp. 1453–1468, Sept. 2025, doi: 10.17798/bitlisfen.1655093.

ISNAD

Aytemiz, Fevzi - Yüksek, Haydar. “Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules As Antioxidant and Antibacterial Agents”. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi 14/3 (September 1, 2025): 1453-1468. https://doi.org/10.17798/bitlisfen.1655093.

JAMA

1.Aytemiz F, Yüksek H. Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl/Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules as Antioxidant and Antibacterial Agents. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi. 2025;14:1453–1468.

MLA

Aytemiz, Fevzi, and Haydar Yüksek. “Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules As Antioxidant and Antibacterial Agents”. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, vol. 14, no. 3, Sept. 2025, pp. 1453-68, doi:10.17798/bitlisfen.1655093.

Vancouver

1.Fevzi Aytemiz, Haydar Yüksek. Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl/Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules as Antioxidant and Antibacterial Agents. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi. 2025 Sep. 1;14(3):1453-68. doi:10.17798/bitlisfen.1655093