503-87-7

Basic information

• Product Name: 2-Thiohydantoin
• Synonyms: 2-THIOHYDANTION;2-THIOHYDANTOIN;2-Thioguidanthion;2-thio-hydantoi;2-thioxo-4-imidazolidinon;2-Thioxo-4-imidazolidinone;2-Thioxo-4-imidazolinone;4-Imidazolidinone,2-thioxo-
• CAS NO: 503-87-7
• Molecular Formula: C₃H₄N₂OS
• Molecular Weight: 116.14
• EINECS: 207-977-4
• Product Categories: Ring Systems;Building Blocks;Heterocyclic Building Blocks;Imidazolines/Imidazolidines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 503-87-7.mol

Chemical Properties

• Melting Point: 229-231 °C (dec.)(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: White/Crystalline Powder
• Density: 1.346 (estimate)
• Vapor Density: 4 (vs air)
• Refractive Index: 1.6550 (estimate)
• Storage Temp.: Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.50±0.10(Predicted)
• CAS DataBase Reference: 2-Thiohydantoin(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiohydantoin(503-87-7)
• EPA Substance Registry System: 2-Thiohydantoin(503-87-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: MU4200000
• TSCA: Yes
• Hazardous Substances Data: 503-87-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Thiohydantoin is used as a reactant for the synthesis of drugs with antidiabetic activity, helping to develop medications that can manage and treat diabetes.
Used in Antimicrobial Applications:
In the pharmaceutical industry, 2-Thiohydantoin is also used as a reactant for the synthesis of barbituric acid and thiohydantoin derivatives with antimicrobial activity, contributing to the development of antibiotics and antifungal agents.
Used in Anticancer Applications:
2-Thiohydantoin is used as a reactant for the synthesis of possible anticancer agents, playing a role in the development of new treatments for cancer.
Used in Fibroblast Growth Factor Receptor 1 Kinase Inhibitors:
2-Thiohydantoin is used as a reactant for the synthesis of fibroblast growth factor receptor 1 kinase inhibitors, which are important in the treatment of various diseases, including cancer.
Used in HIV-1 Integrase Inhibitors:
In the pharmaceutical industry, 2-Thiohydantoin is used as a reactant for the synthesis of HIV-1 integrase inhibitors, which are crucial in the development of antiretroviral drugs for the treatment of HIV/AIDS.
Used in Chemical Industry:
2-Thiohydantoin is used as a reactant for persilylation, a chemical process that involves the introduction of a silyl group into a molecule, which is important in various chemical reactions and synthesis.

InChI:InChI=1/C3H4N2OS/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7)

Upstream product

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• 7245-61-6 N-[(benzoylamino)thioxomethyl]glycine 
• 4743-52-6 N-(o-carboxybenzoyl)glycine 
• 1147550-11-5 ammonium thiocyanate 
• 861364-40-1 1-hippuroyl-2-thioxo-imidazolidin-4-one 
• 102451-51-4 1-(N-hippuroyl-glycyl)-2-thioxo-imidazolidin-4-one 
• 24066-82-8 ethyl 2-isothiocyanatoacetate 
• 24197-65-7 S-phenyl α-chlorothioacetate 
• 17356-08-0 thiourea 
• 333-20-0 potassium thioacyanate 
• 459-73-4 GlyOEt*HCl 
• 591-08-2 acetylthiourea 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 110830-18-7 (5Z)-5-(furan-2-ylmethylene)-2-thioxoimidazolidin-4-one 
• 583-46-0 5-benzylidene-2-thiohydantoin 
• 10258-18-1 (5Z)-5-((1H-indol-3-yl)methylene)-2-thioxoimidazolidin-4-one 
• 28824-65-9 5-Piperonyliden-2-thiohydantoin 
• 6288-76-2 5-(3-methyl-cyclohexyLiDene)-2-thioxo-imidazolidin-4-one 
• 91121-77-6 5-cyclohexanone-2-thiohydantoin 
• 37428-88-9 5-(4-chloro-benzylidene)-2-thioxo-imidazolidin-4-one 

Relevant articles and documents

A simple synthesis of 2-thiohydantoins

2-Thiohydantoin derivatives are produced by heating a mixture of thiourea and an a-amino acid. The method described offers the advantages of simplicity, low cost, easy work-up and scalability.

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.

Utility of 3-(thiophen-2-yl)prop-2-enoyl isothiocyanate in heterocyclic synthesis

Convenient syntheses of quinazoline, benzothiazole, thiadiazole, imidazole, and thiourea derivatives starting from 3-(thiophen-2-yl)prop-2-enoyl isothiocyanate are described. The structures of the synthesized compounds are confirmed from their microanalytical and spectral data. Some of the products are examined for their antibacterial activity against Gram-positive and Gram-negative bacteria and fungi.

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.

Inhibition of Cancer-Associated Mutant Isocitrate Dehydrogenases by 2-Thiohydantoin Compounds

Somatic mutations of isocitrate dehydrogenase 1 (IDH1) at R132 are frequently found in certain cancers such as glioma. With losing the activity of wild-type IDH1, the R132H and R132C mutant proteins can reduce α-ketoglutaric acid (α-KG) to d-2-hydroxyglutaric acid (D2HG). The resulting high concentration of D2HG inhibits many α-KG-dependent dioxygenases, including histone demethylases, to cause broad histone hypermethylation. These aberrant epigenetic changes are responsible for the initiation of these cancers. We report the synthesis, structure-activity relationships, enzyme kinetics, and binding thermodynamics of a novel series of 2-thiohydantoin and related compounds, among which several compounds are potent inhibitors of mutant IDH1 with Ki as low as 420 nM. X-ray crystal structures of IDH1(R132H) in complex with two inhibitors are reported, showing their inhibitor-protein interactions. These compounds can decrease the cellular concentration of D2HG, reduce the levels of histone methylation, and suppress the proliferation of stem-like cancer cells in BT142 glioma with IDH1 R132H mutation.

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.

Thiohydantoins: Selective N- and S-functionalization for Liebeskind-Srogl reaction study

Thiohydantoins formed by the Schlack-Kumpf protocol were selectively functionalized at the nitrogen, sulfur, or carbon atom to test the Liebeskind-Srogl reaction possibilities. Georg Thieme Verlag Stuttgart. New York.

Facile synthesis of hydantoins and thiohydantoins in aqueous solution

A series of hydantoins and thiohydantoins have been synthesized in water at room temperature from urea (or N-methylurea, or thiourea) and simple aldehydes (as glyoxal, and its simple derivatives) in the presence of phosphoric anhydride. The reaction time is 10 min using an equimolar amount of P 4O10 with respect to the other reagents, but the reaction occurs also, even if with longer reaction times, with very small amounts of P4O10. In addition, this method provides a clean and 'green' approach to hydantoins, compounds of great interest in biological and pharmacological fields.

α-Thioureidoalkylation of urea heteroanalogs

α-Thioureidoalkylation of urea heteroanalogs such as thiosemicarbazide, amino-guanidine, sulfamide, and sulfonamides with 4,5-dihydroxyimidazolidine-2-thiones has been studied. Previously unknown 4,5-bis[thiosemicarbazido(guanidinoamino)]imidazolidine-2-thiones, 5,7-dialkylperhydroimidazo[4,5- e][1,2,4]triazine-3,6-dithiones, 4,6-diethyl-5(3H)-thioxotetrahydro-1 H-imidazo[4,5- c][1,2,5]thiadiazole 2,2-dioxide, and 1,3-dialkyl-4-[guanidinoimino(arylsulfonylimino)]imidazolidine- 2-thiones have been synthesized.