1-[[(2R,3S)-2-(2,5-Difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole
[CAS# 241479-73-2]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Antifungal drugs
• Name: 1-[[(2R,3S)-2-(2,5-Difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole
• Synonyms: (2R,3S)-2-(2,5-Difluorophenyl)-3-methyl-[(1H-1,2,4-triazol-1-yl)methyl]oxirane
• Molecular Formula: C₁₂H₁₁F₂N₃O
• Molecular Weight: 251.23
• CAS Registry Number: 241479-73-2
• SMILES: C[C@H]1[C@](O1)(CN2C=NC=N2)C3=C(C=CC(=C3)F)F

Properties

• Solubility: Practically insoluble (0.065 g/L) (25 °C), Calc.^*
• Density: 1.41±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.613, Calc.^*
• Boiling Point: 386.5±52.0 °C (760 mmHg), Calc.^*
• Flash Point: 187.6±30.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

1-[[(2R,3S)-2-(2,5-Difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole is a chemical compound with significant potential in the field of medicinal chemistry. It is a member of the triazole family, which is known for its bioactivity in a range of therapeutic areas. This compound, characterized by a triazole ring and an epoxide group, represents an intriguing scaffold for drug discovery, particularly due to its structural features that enable interactions with various biological targets.

The discovery of this compound was part of efforts to develop new agents for the treatment of diseases caused by bacterial, fungal, and viral infections. The triazole ring, which is known for its stability and ability to form hydrogen bonds, plays a key role in binding to the target enzyme or receptor, thereby exerting its pharmacological effects. The presence of the oxirane (epoxide) group adds another layer of reactivity, which may contribute to its interactions with biological systems, particularly in enzyme inhibition or cellular signaling pathways.

The application of 1-[[(2R,3S)-2-(2,5-Difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole is primarily in the area of drug design and discovery. One of the most promising applications lies in its potential as an antifungal agent. Triazoles are widely recognized for their ability to inhibit fungal growth by targeting enzymes involved in the synthesis of ergosterol, a critical component of fungal cell membranes. The structural features of this compound make it a candidate for the development of new antifungal agents that can overcome resistance mechanisms often encountered in current treatments.

In addition to its antifungal activity, 1-[[(2R,3S)-2-(2,5-Difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole is being explored for its potential antiviral properties. Recent studies have shown that triazole derivatives can inhibit viral replication by interfering with the enzymatic processes essential for viral life cycles. This suggests that the compound could be useful in treating viral infections, particularly in cases where conventional antiviral treatments are ineffective or where resistance has developed.

The compound’s ability to interact with specific biological targets has also led to its consideration in the context of cancer treatment. Some triazole derivatives have shown anticancer activity by inhibiting enzymes involved in cell division and survival, making this compound a potential candidate for further research in oncology.

Furthermore, the fluorine substitution in the aromatic ring enhances the compound's lipophilicity and metabolic stability, properties that are desirable in drug development. Fluorine atoms can also influence the compound’s binding affinity to biological receptors, making this compound a valuable tool for further optimization in drug discovery.

While 1-[[(2R,3S)-2-(2,5-Difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole has demonstrated promising activity in preliminary studies, its full potential is yet to be realized. Researchers are continuing to explore its pharmacological properties, optimize its structure, and evaluate its effectiveness in preclinical and clinical trials. If successful, this compound could provide a new option in the treatment of infections and other diseases, particularly in the face of increasing resistance to existing drugs.

In conclusion, 1-[[(2R,3S)-2-(2,5-Difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole is a chemical compound with diverse applications in medicinal chemistry. Its structural features make it a promising candidate for the development of new antifungal, antiviral, and potentially anticancer therapies. Continued research into its properties and applications may lead to the development of effective new treatments for a variety of diseases.

References

none