Potential antibacterial and antifungal activities of novel sulfamidophosphonate derivatives bearing the quinoline or quinolone moiety

Abstract

A series of new α‐sulfamidophosphonate/sulfonamidophosphonate ( 4a – n ) and cyclosulfamidophosphonate ( 5a – d ) derivatives containing the quinoline or quinolone moiety was designed and synthesized via Kabachnik–Fields reaction in the presence of ionic liquid under ultrasound irradiation. This efficient methodology provides new 1,2,5‐thiadiazolidine‐1,1‐dioxide derivatives 5a – d in one step and optimal conditions. The molecular structures of the novel compounds 4a – n and 5a – d were confirmed using various spectroscopic methods. All these compounds were evaluated for their in vitro antibacterial activity against Gram‐negative ( Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) and Gram‐positive ( Staphylococcus aureus ATCC 27923) bacteria, in addition to three clinical strains ( E. coli 1, P. aeruginosa 1, and S. aureus 1). Most of the tested compounds showed more potent inhibitory activities against both Gram‐positive and ‐negative bacteria compared with the sulfamethoxazole reference. The following compounds, 4n , 4f , 4g , 4m , 4l , 4d , and 4e , are the most active sulfamidophosphonate derivatives. Furthermore, these molecules gave interesting zones of inhibition varying between 28 and 49 mm, against all tested bacterial strains, with a low minimum inhibitory concentration (MIC) value ranging from 0.125 to 8 μg/ml. All the synthesized derivatives were also evaluated for their in vitro antifungal activity against Fusarium oxyporum f. sp. lycopersici and Alternaria sp. The results revealed that all the synthesized compounds exhibited excellent antifungal inhibition and the compounds 4f , 4g , 4m , and 4i were the most potent derivatives with MIC values ranging from 0.25 to 1 µg/ml against the two tested fungal strains. The strongest inhibition of bacteria and fungi strains was detected by the effect of quinolone and sulfamide moieties.

Synthesis and potential antimicrobial activity of novel α-aminophosphonates derivatives bearing substituted quinoline or quinolone and thiazole moieties

“…In continuation of our previous research project [48,49] toward the development and synthesis of novel biomolecule compounds contain α-aminophosphonate moiety in high yields and clean conditions, in this study, we reported and used our previous strategy for the synthesis of new α-aminophosphonate (9a-h) and (10i-l) derivatives using the ionic liquid [TEAA] under US irradiation. We have found that the ionic liquid [TEAA] presented several advantages for the synthesis of α-aminophosphonate derivatives, such as giving pure product without chromatography purification and excellent yield in short reaction time with a simple workup.…”

Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

“…A series of new α-sulfamidophosphonates and cyclosulfamidophosphonates incorporating quinoline or a quinolone moiety was synthesized by the Kabachnik–Fields reaction in the presence of a suitable ionic liquid under ultrasound irradiation [ 71 ].…”

Synthesis, Antimicrobial, and Antibiofilm Activities of Some Novel 7-Methoxyquinoline Derivatives Bearing Sulfonamide Moiety against Urinary Tract Infection-Causing Pathogenic Microbes

“…As a result of the literature review, some new quinoline derivatives that exhibited excellent antibacterial activity were used to design our target compounds, as shown in Figure 2. Bazin et al [51] reported the diethyl ((N-(4-bromophenyl) sulfamoyl) (2-chloro-8-methylquinolin-3-yl) methyl) phosphonate A to have a very potent activity against E. coli, with an MIC of 0.125 µg/mL. Moreover, the quinoline benzodioxole derivative B showed excellent antibacterial activity, with an MIC of 3.125 µg/mL against E. coli and S. aureus strains [52].…”