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Introduction to 5-Amino-1-Methyl-1,2,3,4-Tetrahydropyrimidine-2,4-Dione (CAS No. 23899-79-8)

5-Amino-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione, with the CAS number 23899-79-8, is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound belongs to the class of pyrimidines and is characterized by its unique structure and potential biological activities. In this article, we will delve into the chemical properties, synthesis methods, biological applications, and recent research advancements of 5-amino-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione.

Chemical Structure and Properties

5-Amino-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione is a cyclic compound with a molecular formula of C₇H₁₀N₄O₂. Its molecular weight is approximately 178.18 g/mol. The compound features a tetrahydropyrimidine ring with an amino group and a methyl group attached to the nitrogen atoms at positions 5 and 1, respectively. The presence of these functional groups imparts unique chemical properties to the molecule. For instance, the amino group can participate in hydrogen bonding and other intermolecular interactions, while the methyl group can influence the compound's lipophilicity and solubility.

Synthesis Methods

The synthesis of 5-amino-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione has been extensively studied due to its potential applications in drug development. One common synthetic route involves the reaction of urea with a suitable amine and aldehyde under appropriate conditions. For example, a typical synthesis method involves the condensation of urea with ethyl acetoacetate and formaldehyde in an acidic medium followed by cyclization to form the desired product. Recent advancements in green chemistry have also led to the development of more environmentally friendly synthetic methods that minimize waste and reduce energy consumption.

Biological Activities and Applications

5-Amino-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione has shown promising biological activities that make it a valuable candidate for various pharmaceutical applications. One of its key properties is its ability to act as an inhibitor of specific enzymes involved in metabolic pathways. For instance, studies have demonstrated that this compound can inhibit the activity of dihydroorotate dehydrogenase (DHODH), an enzyme crucial for pyrimidine biosynthesis in cells. This inhibition can have therapeutic implications in diseases such as cancer and autoimmune disorders.

In addition to its enzymatic inhibition properties, 5-amino-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione has also been investigated for its potential as an antiviral agent. Research has shown that it can interfere with viral replication processes by targeting specific viral proteins or enzymes. This makes it a potential candidate for the development of antiviral drugs against various viral infections.

Clinical Trials and Research Advancements

The potential therapeutic applications of 5-amino-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione have led to several clinical trials aimed at evaluating its safety and efficacy. Recent studies have focused on its use as a treatment for cancer and autoimmune diseases. For example, preclinical studies have shown that this compound can induce apoptosis in cancer cells while sparing normal cells. These findings have paved the way for further clinical investigations.

In parallel with clinical trials, ongoing research is exploring new derivatives and analogs of 5-amino-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione. Scientists are using computational methods such as molecular docking and virtual screening to identify compounds with enhanced biological activities and improved pharmacokinetic properties. These efforts aim to optimize the therapeutic potential of this class of compounds.

Conclusion

5-Amino-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (CAS No. 23899-79-8) is a promising compound with diverse biological activities that make it a valuable candidate for pharmaceutical research and development. Its unique chemical structure and properties enable it to interact with various biological targets effectively. Ongoing research continues to uncover new applications and derivatives of this compound, highlighting its potential as a therapeutic agent in various medical conditions.

• 57381-15-4(5-Amino-3-methyl-1H-pyrimidine-2,4-dione)
• 56012-71-6(Urea,N-methyl-N'-(1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)-)
• 17749-91-6(2,4(1H,3H)-Pyrimidinedione, 5-(dimethylamino)-1,3-dimethyl-)
• 289900-59-0(1,3-dimethyl-5-(methylamino)-1,2,3,4-tetrahydropyrimidine-2,4-dione)
• 89073-59-6(5-amino-1,3-diethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione)
• 49738-24-1(5-amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione)
• 1551205-23-2(5-amino-1-[2-(4-methylpiperazin-1-yl)ethyl]pyrimidine-2,4-dione)
• 613241-17-1(2,4(1H,3H)-Pyrimidinedione, 1-ethyl-3-methyl-5-(methylamino)-)
• 860574-41-0(Uracil, 5-amino-3-ethyl (1CI))
• 193014-80-1([1(2H),5'-Bipyrimidine]-2,2',4,4'(1'H,3H,3'H)-tetrone, 3,3'-dimethyl-)