39806-38-7Relevant academic research and scientific papers
Hydrogen-bonding patterns in rac-1-acetyl-5-methyl-2-thioxoimidazolidin-4- one
Sulbaran, Maria E.,Delgado, Gerzon E.,Mora, Asiloe J.,Bahsas, Ali,Novoa De Armas, Hector,Blaton, Norbert
, p. o543-o545 (2007)
In the title compound, C6H8N2O2S, also known as N-acetyl-2-thio-hydantoin- alanine, the mol-ecules are joined by N - H...O hydrogen bonds, forming centrosymmetric R 2 2(8) dimers; these dimers are linked by C - H...O inter-actions to form R 2 2(10) rings, thus forming C 2 2(10) chains that run along the [101] direction. International Union of Crystallography 2007.
Synthesis and antimicrobial activity of thiohydantoins obtained from L-amino acids
Bispo, Marcelle de Lima Ferreira,Garbin, Renata Perugini Biasi,Macedo, Fernando,Nakazato, Gerson,Ogatta, Sueli Fumie Yamada,Ribeiro, Jhonatan Macedo,de Carvalho, Priscila Goes Camargo,de Fátima, ?ngelo
, p. 94 - 102 (2020)
Background: Thiohydantoins are an important class of heterocyclic compounds in drug discovery since they are related to a wide range of biological properties including antimicrobial activity. Objective: The objective of this study was to synthesize a series of thiohydantoins derived from L-aminoacids and to evaluated their inhibitory effect on the growth of Gram-negative and Gram-positive bacteria. Methods: All title compounds were synthetized by reaction of L-amino acids with thiourea or ammonium thiocyanate. Their antimicrobial activities were evaluated against bacterial strains by broth microdilution assays. The time-kill kinetics, the antibiofilm activity and the cytotoxicity to mammalian cells were determined for the compound that exhibited the best antimicrobial profile (1b). Results: Eleven thiohydantoins were readily obtained in good yields (52-95%). In general, thiohydantoins were more effective against Gram-positive bacteria. Compound 1b (derived from L-alanine) showed the best antibacterial activity against Staphylococcus epidermis ATCC 12228 and S. aureus BEC 9393 with MIC values of 940 and 1921 μM, respectively. The time-kill kinetics demonstrated time-dependent bactericidal effect in both strains for this derivative. Besides, 1b also exhibited antibacterial activity against biofilms of S. epidermidis ATCC 12228, leading to a 40% reduction in their metabolic activity compared to the untreated control. No cytotoxicity of 1b to mammalian cells was observed at MIC values. Conclusion: The data reported herein indicate relevant antimicrobial activity of thiohydantoins derived from L-aminoacid, mainly 1b, as potential pharmacophore to guide further chemical modification aiming at the search for new and improved antimicrobial agents.
New methods for the preparation of aryl 2-iminoimidazolidines
O'Donovan, Daniel H.,Rozas, Isabel
supporting information; experimental part, p. 4532 - 4535 (2012/10/07)
A divergent strategy for the synthesis of 1-aryl- and 2-aryl-2- iminoimidazolidines is presented. Cyclization of N-Boc-N′-aryl-N″- (2-hydroxyethyl)guanidines in the presence of methanesulfonyl chloride and triethylamine or sodium hydride at 0 °C affords the corresponding 2-iminoimidazolidines in good yields.
On formation of thiohydantoins from amino acids under acylation conditions
Reyes, Samuel,Burgess, Kevin
, p. 2507 - 2509 (2007/10/03)
Reactions of glycine, alanine, and phenylalanine with acetic anhydride and ammonium thiocyanate give the 1-acetyl-2-thiohydantoins 2a-c. These results appear to contradict prior literature reports pertaining to this reaction.
