503-86-6

Basic information

• Product Name: 2-amino-1,5-dihydro-4H-imidazol-4-one
• Synonyms: 2-amino-1,5-dihydro-4H-imidazol-4-one;2-iminoimidazolidin-4-one;2-Amino-1-imidazoline-4-one;2-Amino-2-imidazoline-4-one;2-amino-1,4-dihydroimidazol-5-one;2-azanyl-1,4-dihydroimidazol-5-one;4H-IMidazol-4-one,2-aMino-3,5-dihydro-
• CAS NO: 503-86-6
• Molecular Formula: C₃H₅N₃O
• Molecular Weight: 99.0913
• EINECS: 207-976-9
• Mol File: 503-86-6.mol

Chemical Properties

• Melting Point: 208-210 °C(Solv: ethanol (64-17-5))
• Boiling Point: 210.2°Cat760mmHg
• Flash Point: 80.9°C
• Appearance: /
• Density: 1.79g/cm³
• Vapor Pressure: 0.195mmHg at 25°C
• Refractive Index: 1.756
• PKA: 10.63±0.20(Predicted)
• CAS DataBase Reference: 2-amino-1,5-dihydro-4H-imidazol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-1,5-dihydro-4H-imidazol-4-one(503-86-6)
• EPA Substance Registry System: 2-amino-1,5-dihydro-4H-imidazol-4-one(503-86-6)

Safety Data

• Hazardous Substances Data: 503-86-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-amino-1,5-dihydro-4H-imidazol-4-one is utilized as a key intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique structure and reactivity allow for the creation of a wide range of medicinal compounds with diverse therapeutic applications.
Used in Agrochemical Production:
In the agrochemical sector, 2-amino-1,5-dihydro-4H-imidazol-4-one serves as a vital component in the development of crop protection agents and other agricultural chemicals. Its incorporation enhances the effectiveness of these products, contributing to improved agricultural yields and pest control.
Used as a Catalyst in Organic Transformations:
2-amino-1,5-dihydro-4H-imidazol-4-one is employed as a catalyst in various organic reactions, facilitating and accelerating the processes to achieve desired outcomes more efficiently. Its use in catalysis underscores its importance in the field of organic chemistry.
Used in the Preparation of Heterocyclic Compounds:
As a reagent, 2-amino-1,5-dihydro-4H-imidazol-4-one is instrumental in the synthesis of heterocyclic compounds, which are prevalent in many areas of chemistry, including pharmaceuticals, materials science, and natural products.
Used in Antimicrobial Applications:
2-amino-1,5-dihydro-4H-imidazol-4-one has been studied for its antimicrobial properties, making it a potential candidate for use in applications aimed at controlling microbial growth, such as in disinfectants and preservatives.
Used in Antitumor Research:
The antitumor potential of 2-amino-1,5-dihydro-4H-imidazol-4-one is under investigation, with its possible use in oncology for the development of novel therapeutic agents targeting cancer cells.

InChI:InChI=1/C3H5N3O/c4-3-5-1-2(7)6-3/h1H2,(H3,4,5,6,7)

Upstream product

• 352-97-6 guanidineacetic acid 
• 420-04-2 CYANAMID 
• 113-00-8 guanidine nitrate 
• 459-73-4 GlyOEt*HCl 
• 1161836-38-9 C₂HF₃O₂*C₆H₁₂N₄O₂ 
• 77287-34-4 formamide 
• 133910-48-2 1-carbobenzoxy-2-iminohydantoin 
• 131543-46-9 Glyoxal 
• 7732-18-5 water 
• 50-01-1 guanidine hydrochloride 
• 64-17-5 ethanol 

Downstream Products

• 25046-23-5 1-acetylhydantoin 
• 520-45-6 Dehydracetic acid 
• 144-62-7 oxalic acid 
• 113-00-8 guanidine nitrate 
• 349636-50-6 5-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)benzylidene]imidazolidine-2,4-dione 
• 352-97-6 guanidineacetic acid 
• 1263777-59-8 2-amino-5-{[5-(4-nitro-phenyl)-furan-2-yl]methylene}-3,5-dihydroimidazol-4-one 

Relevant articles and documents

Marine-derived 2-aminoimidazolone alkaloids. Leucettamine B-related polyandrocarpamines inhibit mammalian and protozoan DYRK & CLK kinases

A large diversity of 2-aminoimidazolone alkaloids is produced by various marine invertebrates, especially by the marine Calcareous sponges Leucetta and Clathrina. The phylogeny of these sponges and the wide scope of 2-aminoimidazolone alkaloids they produce are reviewed in this article. The origin (invertebrate cells, associated microorganisms, or filtered plankton), physiological functions, and natural molecular targets of these alkaloids are largely unknown. Following the identification of leucettamine B as an inhibitor of selected protein kinases, we synthesized a family of analogues, collectively named leucettines, as potent inhibitors of DYRKs (dual-specificity, tyrosine phosphorylation regulated kinases) and CLKs (cdc2-like kinases) and potential pharmacological leads for the treatment of several diseases, including Alzheimer’s disease and Down syndrome. We assembled a small library of marine sponge- and ascidian-derived 2-aminoimidazolone alkaloids, along with several synthetic analogues, and tested them on a panel of mammalian and protozoan kinases. Polyandrocarpamines A and B were found to be potent and selective inhibitors of DYRKs and CLKs. They inhibited cyclin D1 phosphorylation on a DYRK1A phosphosite in cultured cells. 2-Aminoimidazolones thus represent a promising chemical scaffold for the design of potential therapeutic drug candidates acting as specific inhibitors of disease-relevant kinases, and possibly other disease-relevant targets.

Novel prodrugs with a spontaneous cleavable guanidine moiety

Water-soluble prodrug strategy is a practical alternative for improving the drug bioavailability of sparingly-soluble drugs with reduced drug efficacy. Many water-soluble prodrugs of sparingly-soluble drugs, such as the phosphate ester of a drug, have been reported. Recently, we described a novel water-soluble prodrug based on O–N intramolecular acyl migration. However, these prodrug approaches require a hydroxy group in the structure of their drugs, and other prodrug approaches are often restricted by the structure of the parent drugs. To develop prodrugs with no restriction in the structure, we focused on a decomposition reaction of arginine methyl ester. This reaction proceeds at room temperature under neutral conditions, and we applied this reaction to the prodrug strategy for drugs with an amino group. We designed and synthesized novel prodrugs of representative sparingly soluble drugs phenytoin and sulfathiazole. Phenytoin and sulfathiazole were obtained as stable salt that were converted to parent drugs under physiological conditions. Phenytoin prodrug 3 showed a short half-life (t1/2) of 13?min, whereas sulfathiazole prodrug 7 had a moderate t1/2of 40?min. Prodrugs 3 and 7 appear to be suitable for use as an injectable formulation and orally administered drug, respectively.

Meteorites as catalysts for prebiotic chemistry

From outer space: Twelve meteorite specimens, representative of their major classes, catalyse the synthesis of nucleobases, carboxylic acids, aminoacids and low-molecular-weight compounds from formamide (see figure). Different chemical pathways are identified, the yields are high for a prebiotic process and the products come in rich and composite panels.

Syntheses of N-acylisoxazolidine derivatives, related to a partial structure found in zetekitoxin AB, A golden frog poison

Syntheses of four N-acylisoxazolidine derivatives related to a partial structure of zetekitoxin AB were described. 13C NMR spectra of these compounds could not explain an unusual chemical shift observed in the N-acylisoxazolidine moiety of zete

Decomposition of 1-(ω-aminoalkanoyl)guanidines under alkaline conditions

The decomposition of some NG-(ω-aminoalkanoyl)argininamides, which are key intermediates for the preparation of radiolabeled and fluorescent neuropeptide Y receptor ligands, prompted us to synthesize a small series of simple 1-(ω-aminoalkanoyl)guanidines, and to investigate these model compounds for stability in alkaline buffers. The degradation of acylguanidines was monitored by time resolved UV spectroscopy. The most labile compound, 1-(5-aminopentanoyl)guanidine, decomposed with a half life of 19 s to yield piperidin-2-one (pH 10.4 at 25 °C). In contrast the half life of 1-(6-aminohexanoyl)guanidine is 7.7 h, which is comparable to the hydrolysis of acetylguanidine (t1/2 = 9.6 h) in alkaline solution.

Isolation of a novel protein tyrosine phosphatase inhibitor, 2-methyl-fervenulone, and its precursors from Streptomyces

High-throughput screening identified an extract from Streptomyces sp. IM 2096 with inhibitory activity toward several protein tyrosine phosphatases (PTPs). Four 1,2,4-triazine compounds 2096A-D (1-4) were isolated from this extract and their structures elucidated by interpretation of spectroscopic data and confirmed by degradation and synthesis. The novel glycocyamidine derivatives 1 and 2 are diastereomers and may interconvert. Both are inactive in the PTP inhibition assay. Compounds 1 and 2 are unstable and partially decompose to 3 and glycocyamidine (5) at room temperature. Compound 3, known as MSD-92 or 2-methyl-fervenulone, is a broad-specificity PTP inhibitor with comparable potency to vanadate. The imidazo[4,5-e]-1,2,4-triazine (4), inactive in the PTP-inhibition assay, may be a degradation product of 3.

Synthesis and Anticonvulsant Activity of 2-Iminohydantoins

Iminohydantoins selectively substituted at position C-5 and their 1-carbobenzoxy derivatives have been synthesized, and their anticonvulsant activity was evaluated in mice.In general, the more lipophilic 1-carbobenzoxy iminohydantoins were more potent than the unsubstituted counterparts.Evaluation of the individual enantiomers of the chiral iminohydantoins showed that the anticonvulsant activity resided primarily in the S isomers.In this study, (S)-(+)-1-carbobenzoxy-5-isobutyl-2-iminohydantoin (9a) was the most active member.This compound was not nearly as active as phenythoin against electrically induced convulsions, but was also active against pentylenetetrazole-induced seizures, suggesting a broader clinical potential.The closest analogue of phenytoin, viz., 5,5-diphenyl-2-iminohydantoin (1), failed to show any significant activity.Methylation on N-3 or the imino nitrogen of 1 also did not provide a compound with substantial activity. 2-Thiophenytoin was not active against electoshock seizures and showed only a weak activity against pentylenetetrazole.This study suggested that the structure-activity relationship of 2-iminohydantoins was quite different from that of 2-hydantoins.