4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol
[CAS# 1533519-84-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Thiol/thiophenol
• Name: 4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol
• Molecular Formula: C₁₅H₁₃N₃S
• Molecular Weight: 267.35
• CAS Registry Number: 1533519-84-4
• EC Number: 943-285-5
• SMILES: C1CC1C2=CC=C(C3=CC=CC=C23)N4C=NNC4=S

Properties

• Solubility: Insoluble (6.7E^-3 g/L) (25 °C), Calc.^*
• Density: 1.41±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.775, Calc.^*
• Boiling Point: 484.4±38.0 °C (760 mmHg), Calc.^*
• Flash Point: 246.7±26.8 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P337+P317-P362+P364-P501

Discovery and Applications

4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol is a chemical compound that belongs to the class of triazoles, a group known for their diverse biological activities and applications in medicinal chemistry. This particular compound has garnered interest due to its potential in the development of pharmaceuticals, particularly as an agent with antifungal and anticancer properties. The discovery of this substance stems from ongoing research in the area of heterocyclic chemistry, where modifications to the triazole ring and the introduction of various substituents have been explored to enhance biological efficacy and specificity.

The synthesis of 4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol is typically achieved through a reaction involving the nucleophilic substitution of the appropriate halogenated triazole derivative with a cyclopropyl-naphthalene substituent. This structural modification is of particular interest, as the presence of both the triazole and the naphthalene ring systems may influence the compound’s interaction with biological targets, providing it with the potential to exhibit unique pharmacological effects.

In terms of application, 4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol has shown promise in the field of antifungal treatment. The triazole ring is a known pharmacophore in antifungal agents, acting by inhibiting the synthesis of ergosterol, a critical component of fungal cell membranes. This inhibition disrupts the integrity of the cell membrane, ultimately leading to the death of the pathogen. The addition of the cyclopropyl-naphthalene moiety may enhance the compound’s binding affinity and specificity, which could result in increased potency and a broader spectrum of antifungal activity.

Beyond its antifungal properties, research has indicated that 4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol may possess anticancer activity. Triazoles are increasingly being explored as potential agents in cancer therapy, where they may act as modulators of various cellular processes, such as angiogenesis, apoptosis, and cell cycle progression. The compound’s ability to interfere with the growth and proliferation of cancer cells could position it as a lead candidate for further development in the oncology field.

The compound is also being investigated for its potential use in other therapeutic areas, including as a precursor in the synthesis of more complex bioactive molecules. The unique combination of the triazole and naphthalene structures opens up possibilities for designing derivatives with enhanced selectivity and fewer side effects, which is a critical consideration in drug development.

In conclusion, 4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol represents a promising compound with significant potential in both antifungal and anticancer drug discovery. Ongoing research and development may lead to the identification of more potent derivatives, expanding the clinical applications of this class of compounds in the treatment of various diseases.

References

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