16097-62-4 | 4-HYDROXY-2-(METHYLTHIO)-6-(TRIFLUOROMETHYL)PYRIMIDINE

CAS:16097-62-4 | 4-HYDROXY-2-(METHYLTHIO)-6-(TRIFLUOROMETHYL)PYRIMIDINE,Description

The compound of interest, 2-(Methylthio)-6-(trifluoromethyl)pyrimidin-4-ol, is a chemical entity that appears to be related to various pyrimidine derivatives with potential biological activities. Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring. The methylthio group (a sulfur-containing substituent) and the trifluoromethyl group are common modifications that can significantly alter the chemical and biological properties of the molecule.

Synthesis Analysis

The synthesis of related pyrimidine derivatives often involves multi-step reactions starting from simple precursors. For instance, the synthesis of dual thymidylate synthase and dihydrofolate reductase inhibitors involves the conversion of 2-amino-6-methylthieno[2,3-d]pyrimidin-4(3H)-one to various substituted compounds through reactions like the Ullmann reaction. Another example is the regioselectively controlled synthesis of N-substituted (trifluoromethyl)pyrimidin-2(1H)-ones, which are synthesized from the cyclocondensation reaction of 4-substituted 1,1,1-trifluoro-4-methoxybut-3-en-2-ones with nonsymmetric ureas or isothiourea sulfates. These methods highlight the versatility of pyrimidine chemistry and the ability to introduce various functional groups to achieve desired properties.

Molecular Structure Analysis

The molecular structure of pyrimidine derivatives can be complex and is often elucidated using techniques such as NMR, IR, Raman, and X-ray crystallography. For example, triorganotin(IV) complexes of a related pyrimidine derivative were characterized using these techniques, providing insights into the geometry and coordination of the tin atoms within the molecules. The molecular structure is crucial for understanding the reactivity and interaction of these compounds with biological targets.

Chemical Reactions Analysis

Pyrimidine derivatives can undergo various chemical reactions, which are essential for their biological activity. For example, the synthesis of 4-trifluoromethylpyrido[1,2-a]pyrimidin-2-ones involves the addition of substituted 2-aminopyridines to activated alkynoates, leading to the formation of trifluoromethyl substituted pyrimidines. These reactions are often carried out under mild conditions, which is advantageous for the synthesis of biologically active compounds.

Physical and Chemical Properties Analysis

The physical and chemical properties of pyrimidine derivatives, such as solubility, melting point, and stability, are influenced by the substituents on the pyrimidine ring. For instance, the introduction of a trifluoromethyl group can increase the metabolic stability of the compound. Additionally, the presence of a methylthio group can affect the compound's electronic properties and its interaction with biological molecules. Understanding these properties is essential for the development of pyrimidine derivatives as pharmaceutical agents.

Scientific Research Applications

Anti-inflammatory Applications

Pyrimidines, including structures similar to 2-(Methylthio)-6-(trifluoromethyl)pyrimidin-4-ol, have shown a wide range of biological activities, including anti-inflammatory properties. Research by Gondkar, Deshmukh, and Chaudhari (2013) outlines the synthesis and in-vitro anti-inflammatory activity of substituted tetrahydropyrimidine derivatives. These compounds exhibited potent in-vitro anti-inflammatory activity, highlighting the potential of pyrimidine derivatives in designing leads for anti-inflammatory drugs (Gondkar, Deshmukh, & Chaudhari, 2013).

Medicinal and Pharmaceutical Industries

The pyranopyrimidine core, closely related to the chemical structure , serves as a precursor in the medicinal and pharmaceutical industries due to its broad synthetic applications and bioavailability. Parmar, Vala, and Patel (2023) reviewed the synthesis of pyrano[2,3-d]pyrimidine scaffolds using diverse hybrid catalysts, showcasing the compound's applicability in developing lead molecules (Parmar, Vala, & Patel, 2023).

Anti-cancer Research

Pyrimidine derivatives have been extensively studied for their anticancer properties. Kaur et al. (2014) focused on pyrimidine-based scaffolds, demonstrating their potential in interacting with various enzymes, targets, and receptors to exhibit anticancer effects. This review emphasizes the significant interest in pyrimidine derivatives as potential anticancer agents (Kaur et al., 2014).

Optoelectronic Materials

In the realm of material science, the incorporation of pyrimidine and quinazoline fragments into π-extended conjugated systems has proven valuable for creating novel optoelectronic materials. Lipunova, Nosova, Charushin, and Chupakhin (2018) discussed the electroluminescent properties and applications of these derivatives in organic light-emitting diodes (OLEDs) and other electronic devices, showcasing the compound's versatility beyond medicinal applications (Lipunova et al., 2018).

Pharmacological Activities

Chiriapkin (2022) provided a comprehensive analysis of pyrimidine derivatives used in medical practice, covering a wide range of pharmacological activities from antiviral to antitumor effects. This analysis serves as a foundation for the further development of new biologically active compounds based on the pyrimidine core (Chiriapkin, 2022).

More Information

Uses