Microwave-assisted synthesis of nicotinonitrile and/or arene-linked bis(chromene-thiazoles) as new VRE and MRSA inhibitors. Issue 24 (17th December 2022)

• Record Type: Journal Article
• Authors: Mekky, Ahmed E. M.; Sanad, Sherif M. H.
• Is Part Of: Synthetic communications. Volume 52:Issue 24(2022)
• Page Start: 2276
• Page End: 2290
• Publication Date: 2022-12-17
• Subjects: Hantzsch thiazole synthesis -- microwave-assisted reactions -- MRSA inhibitors -- multicomponent reactions -- VRE inhibitors; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2022.2144378
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: Two series of nicotinonitrile and/or arene-linked bis(thiazoles) possessing chromene units are efficiently prepared in this study. A one-pot protocol was designed to prepare the target hybrids involved in the reaction of the respective salicylaldehydes, 2-cyanoethanethioamide, and the appropriate bis(α-haloketone). The reaction was irradiated by microwaves at 100 °C for 40–90 min in dioxane and mediated by piperazine to produce the desired products in 84–95% yields. Nicotinonitrile-linked hybrids 2b, and 2c attached to 6-(4-chlorophenyl) or 6-(4-nitrophenyl) units, respectively, had the best antibacterial activity, particularly against Staphylococcus aureus, and Enterococcus faecalis strains. They showed equipotent efficacy to ciprofloxacin with MIC/MBC values in the ranges from 5.9 to 12.0 µM. Additionally, 2c demonstrated comparable inhibitory activity to linezolid against MRSA and VRE strains with MIC/MBC values ranging from 2.9 to 11.8 µM. The Ames mutagenicity test was used to conclude that 2c was not mutagenic to the Salmonella strains. Graphical Abstract: UF0001