15231-27-3

Usage

Main properties

1. Chemical compound
2. Belongs to the class of pyrimidine derivatives
3. Contains an amino group at the 2-position
4. Contains a carbonyl group at the 4-position
5. Potential biological activities
6. Involved in various biochemical processes
7. Used as a building block in synthesis of pharmaceutical drugs and agrochemicals
8. Structural analogs investigated for potential use as anticancer and antiviral agents

Specific content

2-amino-5,6-dihydro-3H-pyrimidin-4-one is a chemical compound belonging to the class of pyrimidine derivatives.
It contains an amino group at the 2-position and a carbonyl group at the 4-position of the pyrimidine ring.
The compound has potential biological activities and is involved in various biochemical processes.
It can be used as a building block in the synthesis of pharmaceutical drugs and agrochemicals.
Structural analogs of the compound have been investigated for their potential as anticancer and antiviral agents.

InChI:InChI=1/C4H7N3O/c5-4-6-2-1-3(8)7-4/h1-2H2,(H3,5,6,7,8)

Upstream product

• 113-00-8 guanidine nitrate 
• 292638-85-8 acrylic acid methyl ester 
• 353-09-3 3-guanidinopropionic acid 

Downstream Products

• 1338095-62-7 1-(3-bromophenyl)-3-(4-oxo-1,4,5,6-tetrahydropyrimidin-2-yl)urea 
• 1338095-66-1 1-(3-cyanophenyl)-3-(4-oxo-1,4,5,6-tetrahydropyrimidin-2-yl)urea 
• 1338095-64-9 1-(3-methylphenyl)-3-(4-oxo-1,4,5,6-tetrahydropyrimidin-2-yl)urea 
• 1338095-61-6 1-(3-chlorophenyl)-3-(4-oxo-1,4,5,6-tetrahydropyrimidin-2-yl)urea 
• 1338095-65-0 3-(4-oxo-1,4,5,6-tetrahydropyrimidin-2-yl)-1-(3-(trifluoromethyl)phenyl)urea 

Relevant academic research and scientific papers

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.

FACILE SYNTHESIS OF 2-AMINO-4(1H)-PYRIMIDINONE DERIVATIVES: CYCLIZATION OF N-SUBSTITUTED GUANIDINES WITH α,β-UNSATURATED ESTERS

2-Amino-5,6-dihydropyrimidin-(1H)-4-one derivatives containing guanidine moiety (3) have been synthesized in excellent yields by the cyclization of free N-substituted guanidines with α,β-unsaturated esters such as methyl acrylate and methyl methacrylate derivatives under mild conditions.