5-(2-Fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione
[CAS# 1150560-59-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 5-(2-Fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione
• Molecular Formula: C₂₀H₁₅F₅N₂O₃
• Molecular Weight: 426.34
• CAS Registry Number: 1150560-59-0
• EC Number: 855-578-4
• SMILES: CC1=C(C(=O)NC(=O)N1CC2=C(C=CC=C2F)C(F)(F)F)C3=C(C(=CC=C3)OC)F

Properties

• Solubility: Insoluble (3.1E^-5 g/L) (25 ºC), Calc.^*
• Density: 1.401±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.538, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Hazard Statements: H319-H360
• Precautionary Statements: P203-P264+P265-P280-P305+P351+P338-P318-P337+P317-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	2	H361
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

5-(2-Fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione is a chemical compound that has gained attention due to its complex molecular structure and potential applications in medicinal chemistry. This molecule consists of a pyrimidinedione core with multiple substituted aromatic rings, including a fluoro group, a trifluoromethyl group, and a methoxy group. Such a structure provides a unique combination of electronic properties that can influence its biological activity and chemical reactivity, making it a valuable compound for research and development in pharmaceutical and material science fields.

The discovery of this compound is part of a broader effort to design pyrimidine derivatives with enhanced bioactivity. Pyrimidinediones are known for their ability to interact with various enzymes and biological targets, and the introduction of halogenated and methoxy-substituted phenyl rings can further optimize their efficacy. The fluoro and trifluoromethyl groups in the structure enhance the molecule's stability, lipophilicity, and metabolic resistance, characteristics that are essential for developing drugs with favorable pharmacokinetic properties. These modifications also help the compound achieve a more potent interaction with specific enzymes or receptors involved in disease processes, such as in cancer or inflammation.

The pharmaceutical applications of 5-(2-fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione have shown promise in the development of anticancer, anti-inflammatory, and antimicrobial agents. Pyrimidine derivatives are well-studied for their ability to inhibit kinases and other signaling molecules critical for the growth and proliferation of cancer cells. The introduction of a methoxy group and halogenated phenyl rings is believed to further increase the selectivity and potency of these compounds, making them promising candidates for targeted therapies.

Additionally, the compound’s ability to inhibit specific enzymes that contribute to the inflammatory process positions it as a potential therapeutic agent in the treatment of diseases such as rheumatoid arthritis and inflammatory bowel disease. The trifluoromethyl and fluoro groups contribute to the compound’s high metabolic stability, which is essential for drugs designed to maintain efficacy over extended periods in the body.

Beyond pharmaceuticals, this compound's unique molecular structure and the properties of its functional groups make it an interesting candidate for material science applications. The trifluoromethyl groups, in particular, provide stability and resistance to chemical degradation, which can be beneficial in the development of high-performance materials such as liquid crystals, organic semiconductors, and polymers. The fluoro and methoxy groups allow for fine-tuning of the molecule's electronic properties, opening up possibilities for use in advanced materials that require precise control over conductivity and optical behavior.

The ongoing research on 5-(2-fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione continues to explore its full potential. Scientists aim to modify its structure further to optimize its bioactivity and broaden its applications, making it an important compound in the development of new therapeutic agents and materials.

References

2018. Elagolix sodium. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-05-0135