Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications

Abstract

Among the nitrogen-containing heterocyclic compounds, triazoles emerge with superior pharmacological applications. Structurally, there are two types of five-membered triazoles: 1,2,3-triazole and 1,2,4-triazole. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules. Both the triazoles and their derivatives have significant biological properties including antimicrobial, antiviral, antitubercular, anticancer, anticonvulsant, analgesic, antioxidant, anti-inflammatory, and antidepressant activities. These are also important in organocatalysis, agrochemicals, and materials science. Thus, they have a broad range of therapeutic applications with ever-widening future scope across scientific disciplines. However, adverse events such as hepatotoxicity and hormonal problems lead to a careful revision of the azole family to obtain higher efficacy with minimum side effects. This review focuses on the structural features, synthesis, and notable therapeutic applications of triazoles and related compounds.

Synthesis, Characterization, and Enzyme Inhibition Properties of 1,2,4-Triazole Bearing Azinane Analogues

“…The pH was adjusted to 6 by dilute HCl (aq) , and precipitates were collected, washed, and dried. (5). Equimolar compound 3 and hydrazine monohydrate (4) were refluxed with methanol (MeOH; 150 mL) in a RB flask for 4 h at room temperature.…”

“… 3 Triazole is a five-member heterocyclic ring with the chemical formula C 2 H 3 N 3 , that contains three nitrogen and two carbon atoms. 4 , 5 It can also be identified in numerous isoforms, 1,2,4-triazole and 1,2,3-triazole, both of which are also regarded as pyrrodiazoles. Triazoles seem to be white-to-pale yellow crystalline with a faint aroma that is water and alcohol soluble or have melting points of 120 and 260 °C, respectively.…”

“…Azolic derivatives like triazole, thiazole, thiadiazole, and oxadiazole are pharmacologically effective components that have been thoroughly examined for numerous bioactivities because of their appropriate use in medicinal chemistry . Triazole is a five-member heterocyclic ring with the chemical formula C 2 H 3 N 3 , that contains three nitrogen and two carbon atoms. , It can also be identified in numerous isoforms, 1,2,4-triazole and 1,2,3-triazole, both of which are also regarded as pyrrodiazoles. Triazoles seem to be white-to-pale yellow crystalline with a faint aroma that is water and alcohol soluble or have melting points of 120 and 260 °C, respectively .…”

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

“…In view of the important application of triazole scaffolds in pharmaceutical intermediates, it is very significant to find a more effective synthetic method. 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 ).…”

Synergistic Organoboron/Palladium Catalysis for Regioselective N-Allylations of Azoles with Allylic Alcohols

“…Regioselective N-functionalization of azoles is a significant challenge, given the numerous applications of such heterocycles, including as pharmacophores in medicinal chemistry and as binding motifs in coordination chemistry. − Although numerous and diverse approaches have been reported, − the development of catalytic methods that can be applied to diverse substrate types and electrophile classes remains an important goal. Our group has shown that diarylborinic acid catalysts (Ar 2 BOH) activate azole-type heterocycles toward regioselective functionalizations with epoxides and electron-deficient alkenes (Scheme ).…”