1627-30-1

Usage

Uses

Used in Pharmaceutical Industry:
4-METHYL-2H-[1,2,4]TRIAZINE-3,5-DIONE is used as a precursor in the synthesis of barbiturates for its potential sedative, hypnotic, and anticonvulsant properties. It serves as a key building block in the development of central nervous system depressants, which are essential in treating various conditions such as anxiety, insomnia, and seizures.
Used in Antimicrobial Applications:
4-METHYL-2H-[1,2,4]TRIAZINE-3,5-DIONE is studied for its potential antimicrobial properties, making it a candidate for use in the development of new antibiotics or antimicrobial agents. Its ability to target and inhibit the growth of harmful microorganisms could contribute to the fight against antibiotic-resistant bacteria and other pathogens.
Used in Anticancer Research:
4-METHYL-2H-[1,2,4]TRIAZINE-3,5-DIONE is being investigated for its potential anticancer properties, as it may have the ability to target and inhibit the growth of cancer cells. Its use in the development of new anticancer drugs could provide additional treatment options for patients and contribute to the advancement of cancer therapy.

InChI:InChI=1/C4H5N3O2/c1-7-3(8)2-5-6-4(7)9/h2H,1H3,(H,6,9)

Upstream product

• 4338-50-5 2-acetyl-2H,3H,4H,5H-[1,2,4]-triazin-3,5-dione 
• 74-88-4 methyl iodide 
• 104-15-4 toluene-4-sulfonic acid 
• 88512-99-6 2-acetyl-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione 

Relevant academic research and scientific papers

Synthesis, in vitro and in vivo evaluation of [O-methyl-11C] 2-{4-[4-(3-methoxyphenyl)piperazin-1-yl]-butyl}-4-methyl-2H-[1,2,4]-triazine-3, 5-dione: A novel agonist 5-HT1A receptor PET ligand

Synthesis and in vivo evaluation of 2-{4-[4-(3-methoxyphenyl)piperazin-1- yl]-butyl}-4-methyl-2H-[1,2,4]triazine-3,5-dione (5 or MMT), a high affinity and selective serotonin 5-HT1AR agonist PET tracer, are described. GTPγS assay shows that MMT

C?H Methylation of Iminoamido Heterocycles with Sulfur Ylides**

The direct methylation of N-heterocycles is an important transformation for the advancement of pharmaceuticals, agrochemicals, functional materials, and other chemical entities. Herein, the unprecedented C(sp2)-H methylation of iminoamido heterocycles as nucleoside base analogues is described. Notably, trimethylsulfoxonium salt was employed as a methylating agent under aqueous conditions. A wide substrate scope and excellent level of functional-group tolerance were attained. Moreover, this method can be readily applied to the site-selective methylation of azauracil nucleosides. The feasibility of gram-scale reactions and various transformations of the products highlight the synthetic potential of the developed method. Combined deuterium-labeling experiments aided the elucidation of a plausible reaction mechanism.

An improved synthesis of the 5-HT1A receptor agonist Eptapirone free base

Eptapirone free base, F11440,4-methyl-2-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-1,2,4-triazine-3,5(2H,4H)-dione, represents a potent and selective 5-HT1A receptor agonist with high efficacy and the potential to regulate anxiety disorders. Herein, we report a method to retro-synthesize eptapirone free base. The compound consists of heterocyclic aromatic portion and aliphatic portion, and the synthetic route consisted of a total of nine steps with an overall yield of 8.8% starting from the commercially available materials. The key steps in the synthetic method involved: (1) using sodium hydroxide and ethylene glycol as solvent resulted in a better cyclization and yield (61.6%) of 1,2,4-triazine-3,5(2H,4H)-dione; (2) an acceptable yield (63.1%) of 4-tert-butyl(pyrimidin-2-yl)piperazine-1-carboxylate was obtained under an optimized conditions of using triethylamine as a base, ethanol as a solvent, and a reaction temperature of 50?°C for 16?h with non-metal catalysis and less byproducts; (3) the reaction step of eptapirone could get a better yield (49.6%) with an optimized condition of potassium carbonate as a base, acetonitrile as a solvent, NaI as a catalyst, and a reaction temperature of 50?°C for 12?h by nucleophilic substitution reaction. The main advantages of this route were an acceptable product purity, the commercial availability of all starting materials and the absence of high temperature, high pressure and noble metal catalysts, which could result in more feasible commercial applications.

Full synthesis method of eptapirone

The invention discloses a full synthesis method of eptapirone. The full synthesis method comprises the following steps: (1) taking aminourea hydrochloride and trichloracetic aldehyde as raw materialsand carrying out a series of reaction to obtain 2-[2-(aminocarbonyl)hydrazono](CD-1); (2) synthesizing 6-azauracil(CD-2) by the 2-[2-(aminocarbonyl)hydrazono] under the action of sodium hydroxide; (3)taking the 6-azauracil and acetic anhydride to react to obtain 2-acetyl-2H-[1,2,4]triazine-3,5(2H,4H)-diketone(CD3); (4) taking the 2-acetyl-2H-[1,2,4]triazine-3,5(2H,4H)-diketone to react to obtain3-methyl-6-azauracil(CD-4); (5) taking the 3-methyl-6-azauracil to react to obtain 2-(4-chlorobutyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-diketone(CD-5); (6) taking 2-bromopyrimidine, 1-Boc-piperazine and triethylamine to react to obtain 4-(pyrimidine-2-yl)piperazine-1-tert-butyl formate(CD-6); furthermore, reacting to obtain 2-(1-piperazinyl)pyrimidine hydrochloride (1 to 1)(CD-7); (7) taking the 2-(4-chlorobutyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-diketone in step (5) to react with the 2-(1-piperazinyl)pyrimidine hydrochloride in step (6) to obtain the eptapirone(CD-8). The product disclosed by the invention is high in purity and yield and is suitable for industrialized production.

Synthesis and in vivo validation of [O-methyl-11C]2-{4-[4-(7- methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3, 5-dione: A novel 5-HT1A receptor agonist positron emission tomography ligand

Antagonist 5-HT1A PET ligands are available, but an agonist ligand would give more information about signal transduction capacity. Synthesis and in vivo evaluation of [O-methyl-11C]2-{4-[4-(7- methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3, 5-dione (10), a potential high affinity (Ki = 1,36 nM) 5-HT 1A agonist PET tracer is described. Piperazine 10 is a 5-HT 1A agonist with an EC50 comparable to serotonin, based on cAMP formation and GTPγS binding assays. Radiosynthesis of [ 11C]10 has been achieved by reacting 2-{4-[4-(7-hydroxynaphthalen-1- yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3,5-dione (9) and [ 11C]CH3OTf in 25 ± 5% (n = 15) yield at the end of synthesis (EOS). The chemical and radiochemical purities of [11C]10 were >99% with a specific activity 1500 ± 300 Ci/mmol (n = 15). PET studies in anesthetized baboon demonstrate [11C]10 specific binding in brain regions rich in 5-HT1A receptors. Binding of [ 11C]10 was blocked by WAY100635 and 8-OH-DPAT. The regional brain volumes of distribution (VT) of [11C]10 in baboon correlate with [11C]WAY100635 VT in baboons. These data provide evidence that [11C]10 is the first promising agonist PET tracer for the 5-HT1A receptors.

Cyclohexane derivatives difunctionalised in 1,4 as ligands of 5T H1A receptors

The invention concerns novel cyclohexane derivatives difunctionalised in 1.4 of general formula (1) in which A represents a group such as (IIa) in which Ar itself represents an aromatic structure such as phenyl or pyrimidinyl optionally substituted by one

3,5-dioxo-(2H,4H)-1,2,4-triazine derivatives

Novel 3,5-dioxo-(2H,4H-triazine derivatives of general formula (I): wherein R1 is hydrogen, a C1 -C4 alkyl radical, phenyl C1 -C4 alkyl or phenyl, the phenyl ring being optionally substituted by one o