Two decades of the synthesis of mono- and bis-aminomercapto[1,2,4]triazoles

Abstract

<p>4-Amino-5-mercapto[1,2,4]triazole and its 3-substituted derivatives have proven to be of biological interest and provide access to a new class of biologically active heterocyclic compounds for biomedical applications.</p>

Design, synthesis, characterization and antimicrobial evaluation of some novel hydrazinecarbothioamide, 4‐thiazolidinone and 1,2,4‐triazole‐3‐thione derivatives

“…[5] Triazoles are members of heterocyclic compounds possessing a five-membered ring, that bears two carbon atoms and three nitrogen atoms. [6,7] Triazole derivatives have attracted the interest of researchers due to their wide range of biologic activities like anticonvulsant, [8] antidepressant, [9] antioxidant, [10] anti-inflammatory, [11] analgesic, [12] antinociceptive, [13] antibacterial, [14][15][16] antimycobacterial, [17] antifungal, [15,16,18,19] antiviral, [20] anticancer, [21,22] anti-parasitic, [23] 5α-reductase inhibitory [24] and anti-urease. [25] Also, there are known drugs which are currently being used in the treatment and contain 1,2,4-triazole moiety like fluconazole (antifungal), itraconazole (antifungal), voriconazole (antifungal), rizatriptan (5-hydroxytryptamine 1 receptor subtype agonist/migraine) and ribavirin (antiviral) (Figure 1).…”

Synthesis methods of 1,2,3-/1,2,4-triazoles: A review

“…Others reviews published successively in recent years about 1,2,3- or 1,2,4-triazole compounds, which focused on summarizing the structure–activity relationships (SAR) and synthetic strategy ( Matin et al, 2022 ; Moura and Tomé, 2022 ; Nemallapudi et al, 2022 ). In addition, there are also some reviews focused on the synthesis of mono-/bis-aminomercapto and fused 1,2,4-triazole derivatives ( Gomha et al, 2015 ; Riyadh and Gomha, 2020 ; Riyadh et al, 2022 ). In this review, combined with the progress of triazole synthesis in past 20 years, several main synthetic methods from various nitrogen sources are summarized.…”

Synthetic and Medicinal Perspective of 1,2,4‐Triazole as Anticancer Agents

“…Various synthetic approaches were developed to synthesize 1,2,4-triazole and its derivative's from common precursors like imidates, hydrazone, metal-based approach, cycloaddition reaction etc. [21][22][23][24][25][26] Basically 1,2,4triazole has two tautomeric form, 1H-1,2,4-triazole and 4H-1,2,4-triazole as shown in Figure 1, but 1H-1,2,4triazole is more stable comparatively. [27] 1,2,4-triazole has high affinity with biological receptor and it might be due to its structural rigidity and dipole properties via forming a variety of interactions like electrostatic interactions, p-p conjugation, hydrogen bonding, hydrophobicity, and van der Waals force of interaction.…”

“…1,2,4‐triazoles are derived from pyrazole via substituting carbon by nitrogen atom at position 4, it acts as isosteres of ester, amide and carboxylic acid. Various synthetic approaches were developed to synthesize 1,2,4‐triazole and its derivative's from common precursors like imidates, hydrazone, metal‐based approach, cycloaddition reaction etc [21–26] . Basically 1,2,4‐triazole has two tautomeric form, 1 H ‐1,2,4‐triazole and 4 H ‐1,2,4‐triazole as shown in Figure 1, but 1 H ‐1,2,4‐triazole is more stable comparatively [27] .…”