Synthesis of 2′-(1,2,3-triazoyl)-acetophenones: molecular docking and inhibition ofin vitromonoamine oxidase activity

Abstract

The synthesis of 2′-(1,2,3-triazoyl)-acetophenones by a CuAAC using thiourea as a ligand, molecular docking and MAO activity analyses were performed.

Antidepressant-like Effect of 1-(2-(4-(4-Ethylphenyl)-1H-1,2,3-triazol-1-yl)phenyl)ethan-1-one in Mice: Evidence of the Contribution of the Serotonergic System

“…A previous study has shown that ETAP has the ability to inhibit MAO, an enzyme responsible for the degradation of the biological monoamines serotonin, norepinephrine, and dopamine. The results presented by Costa are in line with the data published by Singh, which demonstrated that compounds from the 1,2,3-triazole class are involved in the inhibition of MAO. MAO is found in two isoforms in the organism, MAO-A and MAO-B, with MAO-A being the isoform that has the highest affinity for degrading serotonin and MAO-B has a higher affinity to dopamine .…”

“…Specifically, the class of 1,2,3-triazoles has been considered promising due to the variety of pharmacological properties it presents, such as the ability to form covalent and hydrophobic interactions with different pharmacological targets . Additionally, this class of compounds exhibits surfactant properties, which allows for binding to different pharmacophores, triggering or blocking biological responses, and making this class an interesting alternative for the development of synthetic drugs. , Among the various activities found, the class of 1,2,3-triazoles has demonstrated evidence of antidepressant activity, as it has been shown to be involved in the inhibition of serotonin reuptake and the inhibition of monoamine oxidase (MAO) enzyme, two mechanisms observed in known antidepressants. , …”

“…In addition to triazoles, acetophenones are also commonly used in medicinal chemistry due to their important structural characteristics for biological recognition, enabling interaction with different binding sites, making this class of compounds widely used in the synthesis of long-chain drugs. , …”

“…18,19 Among the various activities found, the class of 1,2,3-triazoles has demonstrated evidence of antidepressant activity, as it has been shown to be involved in the inhibition of serotonin reuptake and the inhibition of monoamine oxidase (MAO) enzyme, two mechanisms observed in known antidepressants. 20,21 In addition to triazoles, acetophenones are also commonly used in medicinal chemistry due to their important structural characteristics for biological recognition, enabling interaction with different binding sites, making this class of compounds widely used in the synthesis of long-chain drugs. 21,22 1-(2-(4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl)phenyl)ethan-1-one (ETAP) (Figure 1) is a hybrid compound containing 1,2,3-triazole and acetophenone.…”

The use of ultrasound in the South Cone region. Advances in organic and inorganic synthesis and in analytical methods

“…Recently, three research groups from Universidade de Pelotas (Brazil), led by Brüning and Alves [45] , described the synthesis of 2′-(1,2,3-triazoyl)-acetophenones ( 126 ) by copper catalyzed azide-alkyne cycloaddition of 2′-azidoacetophenone ( 124 ) with alkynes ( 125 ) ( Scheme 34 ). The corresponding acetophenones ( 126 ) were obtained in moderated to excellent yields under mild conditions in the presence of catalytic amount of copper iodide as catalyst and thiourea as ligand using conventional heating or ultrasound energy.…”