Abstract
Abstract In this study, a series of azobenzothiazole dyes 4 were synthesized via diazotization of substituted benzothiazole derivatives followed by azo coupling with acetaminophen. The chemical structures of all synthesized compounds were confirmed using analytical data and spectroscopic techniques, including UV-visible, IR, mass spectra, and 1H- and 13C-NMR. The in situ formed diazobenzothiazole ions regiospecifically react with acetaminophen derivatives in the Hollemann-guided electrophilic aromatic substitution mechanism. The regio-orientations were established, on the one hand, by a rigorous interpretation of 1H-NMR spectra and, on the other hand, by the characteristic fragmentation patterns observed on the electrospray mass spectra. In the cases of 4a and 4b, multisubstitutions occurred. The antimicrobial activity of compound 4, along with all the starting materials, was investigated on Pseudomonas aeruginosa PA01, Staphylococcus aureus 18, Escherichia coli 64R, and S. aureus ATCC 25923. The results showed that this skeletal framework exhibited marked potency as antibacterial agents. The most active antibacterial agent against both targeted organisms was compound 4a′.
Highlights
In most of our societies, pain and discomfort are often treated with analgesics drugs [1]
To continue our search to find a better combination of pharmacophores within diazo molecules for pharmaceutical applications [16,17,18,19,20], we prepared a series of diazobenzothiazole ions, which were copulated with acetaminophen
The synthetic strategies adopted for the synthesis of the target compounds are depicted in Scheme 1
Summary
In most of our societies, pain and discomfort are often treated with analgesics drugs [1]. The most common side effects associated with the consumption of analgesic drugs are gastrointestinal disorders [4]. One of the advantages of acetaminophen is that it does not cause gastrointestinal problems like most other nonsteroidal anti-inflammatory drugs [1,6], and this is due to acetaminophen’s low affinity for cyclooxygenase (COX). Benzothiazoles are aromatic heterocycles known for their anti-inflammatory [9,10,11], antibacterial [12], antifungal [13], antiviral [14], and antidiabetic [15] activities. To continue our search to find a better combination of pharmacophores within diazo molecules for pharmaceutical applications [16,17,18,19,20], we prepared a series of diazobenzothiazole ions, which were copulated with acetaminophen
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