584-26-9

Usage

Uses

Used in Chemical Synthesis:
1-Acetyl-2-thiohydantoin is used as a synthetic intermediate for the preparation of various chemical compounds. Its unique structural properties allow it to be a valuable building block in the synthesis of complex organic molecules, particularly in the pharmaceutical and chemical industries.
Used in Pharmaceutical Industry:
1-Acetyl-2-thiohydantoin is used as a key component in the development of new pharmaceutical drugs. Its structural versatility enables it to be incorporated into drug molecules, potentially leading to the discovery of novel therapeutic agents with improved efficacy and reduced side effects.
Used in Research and Development:
1-Acetyl-2-thiohydantoin is used as a research compound in academic and industrial laboratories. Its unique chemical properties make it an interesting subject for studying reaction mechanisms, exploring new synthetic routes, and understanding the relationship between molecular structure and biological activity.
Used in Material Science:
1-Acetyl-2-thiohydantoin is used as a component in the development of new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of materials with enhanced properties, such as improved stability, reactivity, or selectivity in various applications.

InChI:InChI=1/C5H6N2O2S/c1-3(8)7-2-4(9)6-5(7)10/h2H2,1H3,(H,6,9,10)

Upstream product

• 1147550-11-5 ammonium thiocyanate 
• 108-24-7 acetic anhydride 
• 56-40-6 glycine 
• 543-24-8 N-acetylglycine 
• 503-87-7 2-thiohydantoin 
• 2620-63-5 2-acetamidoacetamide 
• 463-56-9 thiocyanic acid 

Downstream Products

• 583-46-0 5-benzylidene-2-thiohydantoin 
• 6318-40-7 (5Z)-5-(4-hydroxybenzylidene)-2-thioxoimidazolidin-4-one 
• 95474-45-6 5-p-methoxybenzylidene-2-thiohydantoin 
• 64419-93-8 (Z)-5-ethylidene-2-thioxoimidazolidin-4-one 
• 128365-97-9 4-(N,N-dimethylaminomethylene)-2-thiohydantoin 
• 128365-98-0 4-(β-methyl-N,N-dimethyl)aminomethylene-2-thiohydantoin 
• 51675-47-9 2-(carbamothioylamino)acetic acid 
• 503-87-7 2-thiohydantoin 
• 461-72-3 2,4-imidazolidinedione 
• 99985-06-5 C₁₁H₁₀N₂O₃S 
• 6318-40-7 C₁₀H₈N₂O₂S 
• 1447755-95-4 5-(4-(difluoromethoxy)-3-hydroxybenzylidene)-2-thioxoimidazolidin-4-one 
• 1356003-46-7 1-acetyl-2-(benzylsulfanyl)-4,5-dihydro-1H-imidazol-4-one 

Relevant academic research and scientific papers

Discovery of a structurally novel, drug-like and potent inhibitor of peptidylarginine deiminase

The synthesis and biological properties of a structurally novel, potent and non-peptidic inhibitor of peptidylarginine deiminase are described. The novel drug-like PAD inhibitor contains a 3,5-dihydroimidazol-4-one ring that replaces the acyclic guanidine-binding unit present in arginine residues. This new drug-like PAD inhibitor was effective at 100 nM or below and could have relevance to diseases in which PAD expression is up-regulated, including rheumatoid arthritis, cancer, multiple sclerosis, and neural injury.

1-Acetyl-2-thiohydantoin

In the title compound (1-acetyl-4-oxoimidazolidine-2-thione, C5H6N2O2S), the plane of the acetyl group forms an angle of 6.7° with the essentially planar thiohydantoin ring. N - H...O hydrogen bonds create quasiplanar chains of molecules along the y axis.

Benzylidene 2-aminoimidazolones derivatives: Synthesis and in vitro evaluation of anti-tumor carcinoma activity

A series of benzylidene 2-aminoimidazolones derivatives were synthesized. Most compounds displayed strong inhibitory activity on the proliferation of human HepG2 cells in vitro. The active compounds were further evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against five human cancer cell lines in vitro. Compound 2b exhibited the strongest antitumor activities with IC50 values ranging from 12.87-17.10 μM which were nearly 1-3.5 fold less than that of 5-FU (IC50=18.39-56.12 μM) in vitro. Furthermore, compound 2b could induce SMMC-7721 cell apoptosis in a dose-dependent manner. Therefore, our novel findings may provide a new framework for the design of new benzylidene 2-aminoimidazolones derivatives for the treatment of cancer.

Synthesis and antimicrobial activity of thiohydantoins obtained from L-amino acids

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.

Design and synthesis of biaryloxazolidinone derivatives containing a rhodanine or thiohydantoin moiety as novel antibacterial agents against Gram-positive bacteria

Novel biaryloxazolidinone derivatives containing a rhodanine or thiohydantoin moiety were designed, synthesized and evaluated for their antibacterial activity. The key compounds 7 and 9 were synthesized by the knoevenagel condensation of intermediate aldehyde 5 with rhodanine derivatives 6a?6b. The preliminary study showed that compounds 7, 9 and 10e exhibited potent antibacterial activity with MIC values of 0.125 μg/mL against S. aureus, MRSA, MSSA, LREF and VRE pathogens, using linezolid and radezolid as the positive controls. The most promising compound 10e exhibited potent antibacterial activity against tested clinical isolates of MRSA, MSSA, VRE and LREF with MIC values in the range of 0.125–0.5 μg/mL, and the potency of 10e against clinical isolates of LREF was 64-fold higher than that of linezolid. Moreover, compound 10e was non-cytotoxic with an IC50 value of 91.04 μM against HepG2 cell. Together, compound 10e might serve as a novel antibacterial agent for further investigation.

Highly efficient microwave synthesis of rhodanine and 2-thiohydantoin derivatives and determination of relationships between their chemical structures and antibacterial activity

Here we report studies on the synthesis of 12 new heterocyclic derivatives that differ in three structural motifs and the simultaneous evaluation of the impact of these three variables on the biological properties. The examined compounds are based on rhodanine and 2-thiohydantoin cores equipped with hydrogen or carboxymethyl substituents at the N-3 position and linked to a triphenylamine moiety through 1,4-phenylene, 1,4-naphthalenylene and 1,9-anthracenylene spacers at the C-5 position of the heterocycles. All the compounds were synthesized very quickly, selectively and in high yields according to the developed microwave-assisted Knoevenagel condensation protocol, and they were characterized thoroughly with NMR, FT-IR and ESI-HRMS techniques. The derivatives were tested for their activity against selected strains of Gram-positive and Gram-negative bacteria and yeast. Two compounds showed good activity against Gram-positive bacteria, and all of them showed low cytotoxicity against three cell lines of the human immune system. Based on membrane permeability assays it was demonstrated that the active compounds do not penetrate the cell membrane, and thus they must act on the bacterial cell surface. Finally, we proved that the evaluated structure modifications had a synergistic effect and the simultaneous presence of a 1,4-phenylene spacer and carboxymethyl group at N-3 caused the highest boost in antimicrobial activity.

Heterocycle-containing biaryl oxazolidinone compound and preparation method thereof

The invention relates to a heterocycle-containing biaryl oxazolidinone compound with the structural formula as shown in the figure I in the specification, or an optical isomer and a pharmaceutically acceptable salt and/or solvate thereof, a preparation method for the heterocycle-containing biaryl oxazolidinone compound as well as the optical isomer and the pharmaceutically acceptable salt and/or solvate thereof, and a pharmaceutical composition containing the compound. According to the heterocycle-containing biaryl oxazolidinone compound, the substituent groups R1, R2, R3, R4 and A-ring have the meanings given in the specification. The invention also relates to application of the compound as well as the pharmaceutically acceptable salt and solvate or a prodrug thereof as an antibacterial drug in treatment, especially in treatment of gram-positive bacterial infection and mycobacterium tuberculosis infection. (Please see the figure I in the specification for the structural formula of theheterocyclic ring-containing biaryl oxazolidinone compound.).

A heterocyclic compound and use thereof

The invention relates to a heterocyclic compound as shown in a general formula I which is described in the specification and application of the heterocyclic compound as a plant disease resistance activator. In the general formula I, R1 is selected from the group consisting of hydrogen, a C1-C6 alkyl group and a C3-C6 cycloalkyl group, R2 is selected from the group consisting of hydrogen, a C1-C6 alkyl group, a substituted or non-substituted C1-C14 aryl group and a five-membered or six-membered heterocycle containing nitrogen, oxygen and sulfur, and n is a positive integer in a range of 2 to 4. The compound provided by the invention inhibits pathogens through inducing a plant to generate disease resistance against pathogens instead of directly killing or inhibiting pathogens. The compound provided by the invention has the advantages of systematicness, persistence, broad spectrum activity, security, etc., enables the usage amount of highly toxic pesticides to be reduced and is friendly to the environment; so the compound has great industrial and commercial prospects and a great market value.

Compound capable of inhibiting activity of NEDD8 kinase as well as preparation method and pharmaceutical application of compound

The invention belongs to the field of medicines and in particular relates to a compound with the structure of a formula I, a stereomer of the compound or pharmaceutically acceptable salts of the compound as well as a preparation method of the compound and application of the compound to preparation of anti-tumor medicines. A pharmacological experiment result shows that the compound can be used for inhibiting the activity of NEDD8 kinase and has the inhibition effect on proliferation of a plurality of types of tumor cells, so that the compound can be used as an NEDD8 kinase activity inhibitor for preparing the anti-tumor medicines. The formula I is shown in the description.

PEPTIDYLARGININE DEIMINASES (PAD) INHIBITORS

The present invention relates to compounds of the formula (I): as inhibitors of peptidylarginine deiminases (PADs). It also concerns their use in therapy, particularly in the prophylaxis or treatment of neural injury, and other conditions including cancer, multiple sclerosis, glaucoma, arthritis, rheumatoid arthritis lupus, Alzheimer's disease, and ulcerative colitis.