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A series of 1,2,3-triazoles coupled diaryl sulfone containing compounds were synthesized by the copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reaction in benign solvents under ultrasound irradiation. In situ formation of azides from α-bromoketones together with the CuAAC reaction in one pot allowed safe handling and good availability of azides for the development of a small library of compounds. The sonication reduced reaction time and increased yields compared to otherwise same conditions. All synthesized compounds were evaluated for antibacterial, antifungal and antioxidant activities. Compounds 3b, 6b and 9e-9g were found to be the most potent antifungal agents with minimal inhibitory concentration (MIC) at 25 µg/mL; moreover other compounds revealed good to moderate antimicrobial activity. Compound 8e showed an excellent antioxidant activity using a DPPH free radical scavenging assay. [ABSTRACT FROM AUTHOR]

Abstract: Reaction of aryloxyacetic acid hydrazides 1a,b with α-haloketones such as hydrazonoyl chlorides 2a,b; phenacyl bromides 6a,b; and 2-chloro-N-(1,3-thiazol-2-yl)acetamide 10 led to the formation N-(4-halophenyl)-2-[2-(aryloxyacetyl)hydrazinylidene]propanehydrazonoyl chloride 3a–d; (ethene-1,2-diyl)bis-2-(naphthalen-2-yloxy)acetohydrazides 9a,b; and 2-[(2-aryloxyacetyl)hydrazinyl)]-N-(1,3-thiazol-2-yl)acetamides 11a,b; respectively. The nucleophilic substitution reaction of 3a–d with thiophenol and sodium benzenesulfinate furnished the corresponding hydrazinylidenepropanehydrazonothioates 4a–d and sulfones 5a–d, respectively. The antimicrobial activities of the synthesized compounds were evaluated. The obtained data indicated that the majority of the tested compounds exhibited antibacterial activity while all those compounds showed antifungal activity. Sulfone 5d showed greater effect with all tested organism than well known antibacterial and antifungal agents with minimal inhibitory concentration (MIC) ranged between 4.125 and 16.5 μg/mL. [Copyright &y& Elsevier]

• A new set of hydronaphthalene-sulfonamides were synthesized in a facile approach. • Some of the synthesized agents reveal potent antimicrobial properties. • The promising candidates showed high level of safety towards the human normal cells. • 2D-QSAR model described the antimicrobial properties observed. In the present work, authors successfully prepared potent antimicrobial agents of new tetrahydronaphthalene-sulfonamide derivatives, derived from new easily synthetic route of 3-methoxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride 2. Preparation method of this compound has not been published yet, however it is available commercially expensively, which motivated us to innovate new efficient and facile method for its preparation. All the synthesized compounds were tested for in vitro antimicrobial inhibitory activities against a panel of Gram-positive, Gram-negative bacterial pathological strains and Candida Albicans. Compound 2 showed poor activity towards all of the tested pathogenic strains, but it is easily modified and converted from biologically inactive compound to highly active sulfonamide products 5a-f , or moderately active compounds 3a-k. Cytotoxic evaluation of the promising candidates 5d and 5e showed marked safety profile towards the human normal cells. QSAR study for the new compounds was carried out and was compatible with the antimicrobial results. [Display omitted] [ABSTRACT FROM AUTHOR]