5-Adamantan thiadiazole-based thiazolidinones as antimicrobial agents. Design, synthesis, molecular docking and evaluation.
2018
Аутори:
Fesatidou, MariaZagaliotis, Panagiotis
Camoutsis, Charalampos
Petrou, Anthi
Eleftheriou, Phaedra
Tratrat, Christophe
Haroun, Micheline
Geronikaki, Athina
Ćirić, Ana
Soković, Marina
Тип документа:
Чланак у часопису (Објављена верзија)
,
© 2018 Elsevier Ltd.
Метаподаци
Приказ свих података о документуАпстракт:
In continuation of our efforts to develop new compounds with antimicrobial properties we describe design, synthesis, molecular docking study and evaluation of antimicrobial activity of seventeen novel 2-{[5-(adamantan-1-yl)-1,3,4-thiadiazol-2-yl]-imino}-5-arylidene-1,3-thiazolidin-4-ones. All compounds showed antibacterial activity against eight Gram positive and Gram negative bacterial species. Twelve out of seventeen compounds were more potent than streptomycin and all compounds exhibited higher potency than ampicillin. Compounds were also tested against three resistant bacterial strains: MRSA, P. aeruginosa and E. coli. The best antibacterial potential against ATCC and resistant strains was observed for compound 8 (2-{[5-(adamantan-1-yl)-1,3,4-thiadiazol-2-yl]-imino}-5-(4-nitrobenzylidene)-1,3thiazolidin-4-one). The most sensitive bacterium appeared to be S. typhimirium, followed by B. cereus while L. monocitogenes and M. flavus were the most resistant. Compounds were also tested for their antifungal activity against eight fungal species. All compounds exhibited antifungal activity better than the reference drugs bifonazole and ketokonazole (3-115 times). It was found that compound 8 appeared again to be the most potent. Molecular docking studies on E. coli MurB, MurA as well as C. albicans CYP 51 and dihydrofolate reductase were used for the prediction of mechanism of antibacterial and antifungal activities confirming the experimental results.
Кључне речи:
Adamantan; Antibacterial; Antifungal; CYP51; Dihydrofolate reductase; Docking; MurA; MurB; Thiadiazole; ThiazolidinoneИзвор:
Bioorganic & Medicinal Chemistry, 2018
DOI: 10.1016/j.bmc.2018.08.004
PubMed: 30107969
WoS: 000442887900008
Scopus: 2-s2.0-85051407435
URI
https://www.sciencedirect.com/science/article/pii/S0968089618310277?via%3Dihubhttps://radar.ibiss.bg.ac.rs/handle/123456789/3127