6972-77-6

Usage

Uses

Used in Pharmaceutical Industry:
2-cyano-N-[(methylamino)carbonyl]acetamide is utilized as an intermediate for the synthesis of various drugs, playing a pivotal role in the development of new pharmaceuticals.
Used in Organic Compound Production:
2-cyano-N-[(methylamino)carbonyl]acetamide serves as a building block in the production of other organic compounds, contributing to the diversity and complexity of organic chemistry.
Used in Organic Chemistry Research:
2-cyano-N-[(methylamino)carbonyl]acetamide is employed as a reagent and catalyst in organic chemistry research, enabling the advancement of chemical reactions and the discovery of novel chemical processes.

InChI:InChI=1/C5H7N3O2/c1-7-5(10)8-4(9)2-3-6/h2H2,1H3,(H2,7,8,9,10)

Upstream product

• 4674-68-4 methylcyanamide 
• 372-09-8 cyanoacetic acid 
• 598-11-8 methyluronium nitrate 
• 598-50-5 N-Methylurea 
• 60-29-7 diethyl ether 

Downstream Products

• 2434-53-9 6-amino-1-methyluracil 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 6972-78-7 6-amino-1-methyl-5-nitrosouracil 
• 6632-68-4 6-amino-1,3-dimethyl-5-nitroso-1H-pyrimidine-2,4-dione 
• 23899-79-8 1-methyl-5-amino-2,4(1H,3H)pyrimidinedione 
• 1076-22-8 3-methylxanthine 
• 6972-82-3 5,6-diamino-1-methyluracil 
• 50996-12-8 6-amino-1-methyl-5-nitro-1H-pyrimidine-2,4-dione 
• 63981-33-9 6-amino-1-methyl-3-propyl-1,3-dihydropyrimidine-2,4-dione 

Relevant academic research and scientific papers

Preparation method of theobromine

The invention discloses a preparation method of theobromine, and relates to the technical field of preparation of heterocyclic compounds containing purine ring systems. The method comprises the following steps: adding oxalyl chloride into cyanoacetic acid and a solvent at the temperature of -10-20 DEG C, concentrating to remove the solvent and oxalyl chloride after reaction, adding monomethylureaand the solvent at the temperature of 0-30 DEG C, adding alkali as an acid-binding agent, adding water after reaction, stirring, and filtering to obtain monomethyl cyanoacetylurea; adding water to dissolve cyanuric chloride, adding liquid caustic soda to adjust the pH value to 8-11, and reacting at 80-100 DEG C to generate methyl 4AU; dissolving monomethyl 4AU in formic acid, adding sodium nitrite, reacting at room temperature, adding a catalyst, keeping the temperature at 30-70 DEG C, recovering the catalyst after the reaction is finished, and concentrating mother liquor to recover formic acid, thereby obtaining monomethyl FAU; adding water and liquid caustic soda into monomethyl FAU, carrying out ring-closure reaction, and then adding acid to adjust to be neutral, so as to obtain 3-methyl xanthine; and carrying out a methylation reaction on 3-methylxanthine, and refining to obtain theobromine. The method has the advantages of few reaction steps, few side reactions, high yield and stable product quality.

Synthesis and lipid-lowering evaluation of 3-methyl-1 H-purine-2,6-dione derivatives as potent and orally available anti-obesityagents

Obesity accompanied with metabolic disorder is often complicated with a strong link of dyslipidemia and insulin resistance, whose indicator is the excess accumulation of triglycerides (TG) in cells. Consideration the idea of lipid-lowering and improving insulin resistance, 34 novel compounds by combination the xanthine scaffold with the chain of Rosiglitazone have been synthesized. Among them, several compounds showed efficiency on reducing TG in 3T3-L1 adipoctyes, and 11c exhibited the most optimal capacity in lipid-lowering and improving obese clinical symptoms in DIO mice. Furthermore, the hydrochloride of 11c (11c·HCl) showed excellent bioavailability, 58.94%, over 2 folds than that (28.03%) of 11c, and the anti-obesity effect of 11c·HCl at 50 mg/kg dose was better than that of Metformin at 150 mg/kg dose in DIO mice, almost reversed HFD to a normal level. Thus, 11c·HCl might be a potent and orally available anti-obesity agent via alleviating the obese clinical symptoms, body fat, improving serum parameters and insulin resistance and TG clearance in liver.

Ionic liquid mediated one-pot synthesis of 6-aminouracils

A novel, one-pot synthesis of 6-aminouracils via in situ generated ureas and cyanoacetylureas in the presence of an ionic liquid catalyst, 1,1,3,3-tetramethylguanidine acetate, is described. The catalyst can be recycled for five consecutive runs without loss of activity. The mechanism for the ring closure of cyanoacetylurea to 6-aminouracil is also discussed.

Structure-based optimization of potent and selective inhibitors of the tyrosine kinase erythropoietin producing human hepatocellular carcinoma receptor B4 (EphB4)

The tyrosine kinase EphB4 is an attractive target for drug design because of its recognized role in cancer-related angiogenesis. Recently, a series of commercially available xanthine derivatives were identified as micromolar inhibitors of EphB4 by high-throughput fragment-based docking into the ATP-binding site of the kinase domain. Here, we have exploited the binding mode obtained by automatic docking for the optimization of these EphB4 inhibitors by chemical synthesis. Addition of only two heavy atoms, methyl and hydroxyl groups, to compound 4 has yielded the single-digit nanomolar inhibitor 66, with a remarkable improvement of the ligand efficiency from 0.26 to 0.37 kcal/(mol per non-hydrogen atom). Compound 66 shows very high affinity for a few other tyrosine kinases with threonine as gatekeeper residue (Abl, Lck, and Src). On the other hand, it is selective against kinases with a larger gatekeeper. A 45 ns molecular dynamics (MD) simulation of the complex of EphB4 and compound 66 provides further validation of the binding mode obtained by fragment-based docking. 2009 American Chemical Society.