(alphaS,betaR)-beta-(2,5-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanenitrile
[CAS# 241479-74-3]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: (alphaS,betaR)-beta-(2,5-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanenitrile
• Synonyms: (2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1,2,4-triazol-1-yl)butanenitrile
• Molecular Formula: C₁₃H₁₂F₂N₄O
• Molecular Weight: 278.26
• CAS Registry Number: 241479-74-3
• SMILES: C[C@@H](C#N)[C@](CN1C=NC=N1)(C2=C(C=CC(=C2)F)F)O

Properties

• Solubility: Very slightly soluble (0.16 g/L) (25 ºC), Calc.^*
• Density: 1.32±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.586, Calc.^*
• Boiling Point: 522.5±60.0 ºC (760 mmHg), Calc.^*
• Flash Point: 269.8±32.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

(alphaS, betaR)-beta-(2,5-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanenitrile is a synthetic compound that belongs to the triazole family, a class of compounds with notable biological activity. Its structural complexity, including a triazole ring, a hydroxyl group, a nitrile group, and a difluorophenyl substituent, gives it the potential for significant interactions with various biological targets, making it an interesting candidate for drug discovery and therapeutic development.

The discovery of (alphaS, betaR)-beta-(2,5-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanenitrile is part of ongoing efforts to design new molecules with specific pharmacological properties. The presence of a difluorophenyl group enhances the compound's lipophilicity, which may contribute to its ability to cross biological membranes effectively. The triazole ring, a known pharmacophore in medicinal chemistry, is critical for its bioactivity, particularly in its ability to form interactions with enzymes and receptors that are involved in various disease processes. The nitrile and hydroxyl groups further contribute to its chemical reactivity and potential for enzyme inhibition.

This compound has been primarily studied for its potential in the treatment of fungal infections, as triazoles are well-known for their antifungal activity. Triazoles inhibit the synthesis of ergosterol, a key component of fungal cell membranes, by targeting the enzyme lanosterol demethylase. Given the increasing issue of drug resistance in the treatment of fungal diseases, (alphaS, betaR)-beta-(2,5-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanenitrile could represent a novel agent capable of overcoming resistance mechanisms that limit the efficacy of current antifungal drugs.

In addition to its antifungal activity, the structural features of this compound suggest potential utility in the development of antiviral therapies. Triazole derivatives have been shown to interfere with viral replication in some cases, and (alphaS, betaR)-beta-(2,5-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanenitrile's ability to interact with enzymes essential for viral replication could make it a promising candidate for further investigation in antiviral drug design. The nitrile group could also play a role in enzyme inhibition, which is a key mechanism for many antiviral drugs.

The compound's ability to interact with biological targets, particularly enzymes involved in cell division and survival, suggests that it could also have applications in oncology. Research on triazole derivatives has shown potential in inhibiting enzymes related to cancer cell proliferation, making this compound a candidate for anticancer drug development. Its hydroxyl group could be involved in hydrogen bonding with target proteins, further enhancing its binding affinity to biological targets.

As with many drug candidates, (alphaS, betaR)-beta-(2,5-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanenitrile's effectiveness will need to be evaluated in preclinical and clinical studies. Further research is necessary to determine its toxicity, pharmacokinetics, and overall therapeutic potential. In addition, optimizing its structure to enhance its bioactivity, selectivity, and metabolic stability will be critical in advancing it as a viable drug candidate.

In conclusion, (alphaS, betaR)-beta-(2,5-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanenitrile is a promising compound with potential applications in the treatment of fungal and viral infections, as well as cancer. Its structural features make it an attractive candidate for further research, and its success in drug development could provide new therapeutic options in the face of increasing resistance to existing drugs.

References

2016. Isavuconazole. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-09-0093