Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine.

Teran Teran,Heredia-Moya Heredia-Moya,Beske Beske,Pérez-Barrera Pérez-Barrera,Dobronski Dobronski,Poveda Poveda,Guevara Guevara,Araya-Maturana Araya-Maturana,Mora Mora,Rojas-Silva Rojas-Silva,Barreiro-Costa Barreiro-Costa

doi:10.3390/molecules24152696

Abstract

Our main interest is the characterization of compounds to support the development of alternatives to currently marketed drugs that are losing effectiveness due to the development of resistance. Schiff bases are promising biologically interesting compounds having a wide range of pharmaceutical properties, including anti-inflammatory, antipyretic, and antimicrobial activities, among others. In this work, we have synthesized 12 Schiff base derivatives of 4-aminoantipyrine. In vitro antimicrobial, antioxidant, and cytotoxicity properties are analyzed, as well as in silico predictive adsorption, distribution, metabolism, and excretion (ADME) and bioactivity scores. Results identify two potential Schiff bases: one effective against E. faecalis and the other with antioxidant activity. Both have reasonable ADME scores and provides a scaffold for developing more effective compounds in the future. Initial studies are usually limited to laboratory in vitro approaches, and following these initial studies, much research is needed before a drug can reach the clinic. Nevertheless, these laboratory approaches are mandatory and constitute a first filter to discriminate among potential drug candidates and chemical compounds that should be discarded.

Highlights

In the last decades, antibiotic resistances have been described in several microorganisms, including those having multiresistance phenotypes [1,2,3,4]
These signals are like those reported in the literature, and as expected, the azomethine proton for all compounds with electron-donating groups are shifted to a higher field relative to 3a, except for 3b, which shows a signal at 9.70 ppm, possibly due to an intramolecular hydrogen bond with the hydroxyl group
We synthesized a series of Schiff base derivatives of 4-aminoantipyrine and tested their cytotoxic properties against selected bacteria, fungi, and leishmania parasites, as well their antioxidant/oxidative activities

Summary

Introduction

Antibiotic resistances have been described in several microorganisms, including those having multiresistance phenotypes [1,2,3,4]. This is an alarming situation, as noted by the World. Other authors have suggested the development of new antibiotic classes with novel chemical properties not present in existing classes of antibiotics [6]. In this context, Schiff bases offer an alternative that has not been adequately explored.

Methods

Results

Conclusion