1-[[2-Fluoro-6-(trifluoromethyl)phenyl]methyl]-5-iodo-6-methyl-2,4(1H,3H)-pyrimidinedione
[CAS# 1150560-54-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 1-[[2-Fluoro-6-(trifluoromethyl)phenyl]methyl]-5-iodo-6-methyl-2,4(1H,3H)-pyrimidinedione
• Molecular Formula: C₁₃H₉F₄IN₂O₂
• Molecular Weight: 428.12
• CAS Registry Number: 1150560-54-5
• EC Number: 687-893-6
• SMILES: CC1=C(C(=O)NC(=O)N1CC2=C(C=CC=C2F)C(F)(F)F)I

Properties

• Solubility: Insoluble (1.1E^-3 g/L) (25 °C), Calc.^*
• Density: 1.88±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.600, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H302-H312-H315-H320-H332-H361
• Safety Statements: P203-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P318-P321-P330-P332+P317-P337+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2B	H320
Reproductive toxicity	Repr.	2	H361
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

1-[[2-Fluoro-6-(trifluoromethyl)phenyl]methyl]-5-iodo-6-methyl-2,4(1H,3H)-pyrimidinedione is a compound of interest in the fields of medicinal chemistry and material science. The molecule features a pyrimidinedione ring fused with a phenylmethyl group containing a trifluoromethylated aromatic moiety and a fluoro group, along with an iodine substituent at the 5-position. This unique structural arrangement imparts significant chemical and biological activity, making it a target for synthetic efforts aimed at designing novel pharmaceuticals and functional materials.

The discovery of 1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-5-iodo-6-methyl-2,4(1H,3H)-pyrimidinedione was part of ongoing research into pyrimidine derivatives with enhanced bioactivity. Pyrimidinediones are well-known for their ability to act as enzyme inhibitors, particularly targeting kinases and other signaling molecules involved in various diseases. The incorporation of electron-withdrawing groups such as trifluoromethyl and fluoro in the aromatic ring increases the compound's potency by enhancing its ability to interact with biological receptors and enzymes through non-covalent interactions.

Pharmaceutical applications of 1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-5-iodo-6-methyl-2,4(1H,3H)-pyrimidinedione are primarily centered around its role as a potential anticancer or antiviral agent. The iodine atom in the molecule provides a valuable point for further modification, while the trifluoromethyl group boosts the molecule's metabolic stability and lipophilicity. These features are especially important for the development of orally bioavailable drugs with good pharmacokinetic profiles. Studies have demonstrated that pyrimidine derivatives can inhibit certain cancer-related enzymes, and this compound is being explored for its potential to block specific signaling pathways that are activated in cancer cells.

In addition to its therapeutic potential, the compound's unique structural features make it suitable for use in material science. The trifluoromethyl group imparts enhanced stability and resistance to degradation, which is beneficial in the development of high-performance materials, including liquid crystals and polymers. This makes 1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-5-iodo-6-methyl-2,4(1H,3H)-pyrimidinedione a promising candidate for the design of materials with specific electronic and optical properties.

The molecular design of this compound also allows it to serve as a precursor in the synthesis of other biologically active molecules. By modifying the pyrimidine core or substituting other functional groups on the aromatic ring, chemists can create a library of analogs to further explore structure-activity relationships and optimize bioactivity.

The discovery and applications of 1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-5-iodo-6-methyl-2,4(1H,3H)-pyrimidinedione highlight the importance of fluorine chemistry in developing potent and selective bioactive compounds, with wide-reaching implications in drug design and material innovation.

References

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