64419-93-8Relevant academic research and scientific papers
Combined DFT calculation, Hirshfeld surface analysis, and Energy framework study of non-covalent interactions in the crystal structure of (Z)-5-ethylidene-2-thiohydantoin determined by powder X-ray diffraction
Delgado, Gerzon E.,Mora, Asiloé J.,Seijas, Luis E.,Rincón, Luis,Marroquin, Gustavo,Cisterna, Jonathan,Cárdenas, Alejandro,Brito, Iván
, (2021)
The thiohydantoin core is used in the synthesis and development of new drugs. Furthermore, the study of these materials allows us to analyze the role that non-covalent interactions play in their supramolecular structure and how they can influence their pharmacological properties. Herein, a novel thiohydantoin compound, namely (Z)-5-ethylidene-2-thiohydantoin was synthesized and characterized by FT-IR, 1H-NMR, and 13C-NMR spectroscopy. Its crystal structure was determined and refined by powder X-ray diffraction techniques. This material crystallizes in the monoclinic system with space group P21/c, Z=4. The crystal packing is controlled by N–H···O, N–H···S and C–H···O hydrogen bond interactions, forming infinite two-dimensional sheets with graph-set motifs R22(8), R12(7), and R66(26). NCI calculations, Hirshfeld surface analysis, and the Energy framework study reproduce in good agreement the crystal packing exhibited by the X-ray diffraction study.
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 (2020/02/06)
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.
Studies in thiohydantoin chemistry. II: C-terminal sequencing of peptides
Casagranda, Franca,Duggan, Brendan M.,Kirkpatrick, Alan,Laslett, Robert L.,Wilshire, John F.K.
, p. 551 - 560 (2007/10/03)
An investigation has been carried out into the thiocyanate degradation (AcOH/Ac2O/HSCN) procedure as it relates to the C-terminal sequencing of peptides, particular emphasis being placed on the sequencing of amino acid residues containing sensi
Studies in Thiohydantoin Chemistry. I. Some Aspects of the Schlack-Kumpf Reaction
Duggan, Brendan M.,Laslett, Robert L.,Wilshire, John F. K.
, p. 541 - 550 (2007/10/03)
An investigation has been carried out into the Schlack-Kumpf reaction, i.e., the reaction of amino acids with a mixture of acetic anhydride, acetic acid and sodium thiocyanate (occasionally ammonium thiocyanate was used). particular emphasis was placed on
