Web of Science (Emerging Sources Citation Index), Scopus, ISC

Document Type : Original Research Article

Authors

1 Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad, Baghdad, Iraq

2 Department of Pharmaceutical Chemistry, College of Pharmacy, University of Mosul, Mosul, Iraq

3 Department of Pharmacology and Toxicology, College of Pharmacy, University of Baghdad , Baghdad, Iraq

Abstract

In this research, acetone dicarboxylic acid generated from citric acid was employed in the Pechmann coupling reaction to produce a novel multifunctional benzodipyrone precursor (CSY1). The latter was reacted with a variety of substituted phenols to produce the six CSY1-based derivatives symbolized here as CSY2-CSY7. The chemical structures of the precursor and its based derivative were efficiently recognized by examining the acquired spectral charts. Our compounds' cytotoxic, antimicrobial, and hypoglycemic activities were tested in vitro. The initial activity was evaluated against six tumorigenic cell lines utilizing an IC50 matrix. The antibacterial activity of six aerobic gram-negative bacteria, four anaerobic bacteria, two fungi, and one non-pathogenic bacterial strain was assessed using a broth-dilution test. Furthermore, the hypoglycemic activity on yeast α-glucosidase and porcine α-amylase, two types of blood glucose-controlling enzymes, was calculated. According to the findings of the initial activity, our compounds, notably CSY4, displayed a potent-to-moderate wide-range of cytotoxic properties. This action is accompanied by a low risk of normal cell toxicity. Furthermore, these compounds showed promising antibacterial properties, particularly CSY5 for aerobic gram-negative bacteria, CSY2 for anaerobic bacteria, and CSY1 for pathogenic fungi. This promise is supported by our chemicals' relative safety when it comes to the bacteria of the normal flora. The compounds also had moderate-to-weak inhibitory effects on the blood glucose-controlling enzymes tested, with CSY2 and CSY3 having the strongest hypoglycemic potential. Our molecules, according to the results, could provide unique bioactive platforms that might open up new avenues for the identification of novel therapeutically active drugs.

Graphical Abstract

Synthesis and Biomedical Activities of Novel Multifunctional Benzodipyrone-based Derivatives

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