Synthesis of novel conjugated benzofuran-triazine derivatives: Antimicrobial and in-silico molecular docking studies

Zahra Riyahi; Parvin Asadi; Farshid Hassanzadeh; Elahe Khodamoradi; Alexa Gonzalez; Mahmood Karimi Abdolmaleki

doi:10.1016/j.heliyon.2023.e18759

Synthesis of novel conjugated benzofuran-triazine derivatives: Antimicrobial and in-silico molecular docking studies

Heliyon. 2023 Jul 27;9(8):e18759. doi: 10.1016/j.heliyon.2023.e18759. eCollection 2023 Aug.

Authors

Zahra Riyahi¹, Parvin Asadi^{2

3}, Farshid Hassanzadeh², Elahe Khodamoradi⁴, Alexa Gonzalez⁵, Mahmood Karimi Abdolmaleki⁶

Affiliations

¹ Department of Chemistry, Shahreza Branch, Islamic Azad University, P.O. Box 311-86145, Shahreza, Isfahan, Iran.
² Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, 81746-73461, Iran.
³ Isfahan Pharmaceutical Sciences Research Center, Isfahan University of Medical Sciences, Isfahan, Iran.
⁴ Department of Pharmaceutical Biotechnology, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran.
⁵ Department of Nursing, Texas A&M International University, Laredo, TX 78041, USA.
⁶ Department of Physical and Environmental Sciences, Texas A&M University-Corpus Christi, 6300 Ocean Drive, Corpus Christi, TX 78412, USA.

Abstract

Two new developments of antibacterial agents, a series of benzofuran-triazine based compounds (8a-8h) were designed and synthesized. The derivatives were prepared through conventional chemical reactions and structurally characterized with FT-IR, ¹H and ¹³C NMR techniques. The antibacterial activity of the synthesized derivatives was assessed against gram-positive bacterial strains (Bacillus subtilis, and Staphylococcus aureus) and gram-negative bacterial strains (Salmonella entritidis and Escherichia coli). Compound 8e, with the MIC value of 125-32 μg/μl against all the examined strains of bacteria, was the most active antibacterial compound. The synthesized derivatives were also studied for docking to the binding sites of dihydrofolate reductase (DHFR) receptor which has a key role in drug resistance associated with bacterial infections. The synthesized compounds showed good interaction with the targets through hydrogen bonding and hydrophobic interactions. According to antibacterial and docking studies, compound 8e could be introduced as a candidate for development of antibacterial compounds.

Keywords: Anti-bacterial agent; Benzofuran; In-silico study; Triazine.