26526-57-8Relevant articles and documents
5-Adamantan thiadiazole-based thiazolidinones as antimicrobial agents. Design, synthesis, molecular docking and evaluation
Fesatidou, Maria,Zagaliotis, Panagiotis,Camoutsis, Charalampos,Petrou, Anthi,Eleftheriou, Phaedra,Tratrat, Christophe,Haroun, Micheline,Geronikaki, Athina,Ciric, Ana,Sokovic, Marina
, p. 4664 - 4676 (2018)
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.
Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies
Jakovljevi?, Katarina,Joksovi?, Milan D.,Botta, Bruno,Jovanovi?, Ljiljana S.,Avdovi?, Edina,Markovi?, Zoran,Mihailovi?, Vladimir,Andri?, Marijana,Trifunovi?, Sne?ana,Markovi?, Violeta
, p. 585 - 598 (2019/07/05)
A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole am
Adamantane Derivatives IV: Unexpected Debenzylation on Ring Closure of 1-(1-Adamantylcarbonyl)-4-benzylthiosemicarbazide with Sulphuric Acid
El-Emam, A. A.,Lehmann, J.
, p. 587 - 592 (2007/10/02)
Cyclization of 1-(1-adamantylcarbonyl)-4-substituted thiosemicarbazides 2a-e with sulphuric acid at ambient temperature or by heating with phosphorus oxychloride yielded the corresponding 2-(1-adamantyl)-5-amino-1,3,4-thiadiazoles 3a-e.Cyclization of 1-(1-adamantylcarbonyl)-4-benzylthiosemicarbazide 2f with sulphuric acid gave the debenzylated product 2-(1-adamantyl)-5-amino-1,3,4-thiadiazole 4.On the other hand, cyclization of 2f using phosphorus oxychloride yielded 2-(1-adamantyl)-5-benzylamino-1,3,4-thiadiazole 3f. - Keywords: Adamantanes; Debenzylation; 1,3,4-Thiadiazoles.