Abstract
3-[(2-Hydroxyphenyl)amino]butanoic and 3-[(2-hydroxy-5-methyl(chloro)phenyl)amino]butanoic acids were converted to a series of derivatives containing hydrazide, pyrrole and chloroquinoxaline moieties. The corresponding benzo[b]phenoxazine derivatives were synthesized by the reaction of the obtained compounds with 2,3-dichloro-1,4-naphthoquinone. Five of the synthesized compounds exhibited good antimicrobial activity against Staphylococcus aureus and Mycobacterium luteum, whereas three compounds showed significant antifungal activity against Candida tenuis and Aspergillus niger.
Highlights
The frequency of bacterial and fungal infections is an important contemporary problem due to the emerging new infectious diseases and increasing multi-drug resistance of microbial pathogens [1]
3-[(2-Hydroxyphenyl)amino]butanoic acids 2a–c were obtained by the reaction of the corresponding amines 1a–c with crotonic acid (Scheme 1)
The screening of antimicrobial and antifungal activity of the synthesized compounds has revealed that benzo[b]phenoxazine derivatives 9a–c, 10c, and 12f are active against Gram-positive bacteria S. aureus and M. luteum at lower concentrations
Summary
The frequency of bacterial and fungal infections is an important contemporary problem due to the emerging new infectious diseases and increasing multi-drug resistance of microbial pathogens [1]. The widespread use of antibiotics has contributed to the growing infection rate since fungal infections occur after antibiotic therapy, which has the effect of killing the beneficial bacteria that normally suppress fungi. Β-Amino acids and their derivatives are structural units of various natural compounds, such as peptides, depsipeptides, lactones, alkaloids, and antibiotics. Cyanobacteria, fungi, and plants often incorporate β-amino acids into secondary metabolites. Many natural compounds characterized by potent biological activities are active thanks to the presence of β-amino acid substructure [2]. Benzoquinone and naphthoquinone fragments are often incorporated into the structure of natural biologically active compounds. The biological activity of quinones is related to their ability to accept one and/or two electrons to form the corresponding radical anion or dianion species, as well as the acid-base properties of the compounds. The variable capacity of quinone compounds to accept electrons is due to the electron-attracting (or donating) substituents at the quinone moiety, which modulate the redox properties responsible for the resulting oxidative stress [3]
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