Methyl 2-[[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]thio]acetate
[CAS# 1533519-85-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Methyl 2-[[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]thio]acetate
• Molecular Formula: C₁₈H₁₇N₃O₂S
• Molecular Weight: 339.41
• CAS Registry Number: 1533519-85-5
• EC Number: 938-816-2
• SMILES: COC(=O)CSC1=NN=CN1C2=CC=C(C3=CC=CC=C32)C4CC4

Properties

• Solubility: Insoluble (6.8E^-4 g/L) (25 °C), Calc.^*
• Density: 1.38±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

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

Safety Data

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

Discovery and Applications

Methyl 2-[[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]thio]acetate is a chemical compound of interest due to its unique molecular structure and its potential applications in medicinal chemistry. The compound belongs to the class of thioether-substituted triazoles, a group known for their diverse biological activities. The discovery and development of such compounds have been driven by the need for novel agents with improved pharmacological profiles, particularly in the fields of antifungal and anticancer research.

The synthesis of methyl 2-[[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]thio]acetate typically involves the reaction of a triazole derivative with a thioether group, followed by esterification with methyl acetate. This synthetic route not only provides a method for the introduction of functional groups but also enables the formation of a compound with a specific structure, including the cyclopropyl-naphthalene moiety attached to the triazole ring. This unique structural feature enhances the compound’s potential for biological activity, as the combination of heterocyclic and aromatic systems can modulate the compound’s interactions with cellular targets.

Methyl 2-[[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]thio]acetate has been investigated for its potential antifungal properties. The triazole ring, a well-known pharmacophore in antifungal drug development, inhibits the synthesis of ergosterol, an essential component of fungal cell membranes. By disrupting the integrity of the fungal membrane, the compound exerts its antifungal effects. The addition of the cyclopropyl-naphthalene group could further enhance its activity, possibly improving its binding affinity to fungal targets and expanding the spectrum of activity.

Additionally, the compound is being explored for its potential anticancer properties. Triazole-based compounds are increasingly recognized for their ability to interfere with various cellular processes, such as cell proliferation, apoptosis, and angiogenesis, all of which are important in the development and progression of cancer. The unique substitution pattern in methyl 2-[[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]thio]acetate may enhance its interactions with cancer cell signaling pathways, positioning it as a promising candidate in anticancer drug discovery.

In conclusion, methyl 2-[[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]thio]acetate represents a promising class of triazole-based compounds with potential applications in the treatment of fungal infections and cancer. Further studies are required to fully explore its pharmacological profile and therapeutic potential, which could lead to the development of more selective and effective therapeutic agents.

References

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