Synthesis, structure and α-glucosidase inhibitor activity evaluation of some acetamide derivatives starting from 2-(naphthalen-1-yl) acetic acid, containing a 1,2,4-triazole

Glycosidase-targeting small molecules for biological and therapeutic applications

“…32). 239 Based on the findings that 1,2,4-triazole heterocycles containing sulfur are commonly used in the pharmaceutical industry and that they display good biological activities, a series of 1,2,4-triazole containing compounds were prepared. In the group, 77 was found to have great inhibitory activity (IC 50 = 0.11 μM) against α-glucosidase.…”

Studying the Structure and Evaluating α‐Glucosidase Inhibition of Novel Acetamide Derivatives Incorporating 4‐Ethyl‐4H‐1,2,4‐Triazole Starting from 2‐(Naphthalen‐1‐yl)Acetic Acid

“…[16] Some of these compounds, which were derived from 1,2,4-triazole, also display moderate to good effects as antiproliferative, [17] antioxidant, [18] and anticancer agent. [19] Building on our prior research, [7] N-phenylacetamide derivatives incorporating 1,2,4-triazole, synthesized from 2-(naphthalen-1-yl)acetic acid, have exhibited notable α-glucosidase activity. This activity positions them as potential contenders against diabetes, a widespread condition with α-glucosidase involvement.…”

“…Several contemporary drugs, including antifungals like fluconazole, voriconazole, and itraconazole, anti-convulsant like alprazolam, and anti-viral like ribavirin, feature the 1,2,4-triazole scaffold. [5] Moreover, derivatives containing the latter moiety are recognized for their diverse biological activities, spanning antidiabetic, [6][7][8] α-glucosidase inhibition, [9][10][11] antibacterial, [12] antifungal, [13] antimalarial, [14] antiviral, [15] and antispasmodic properties. [16] Some of these compounds, which were derived from 1,2,4-triazole, also display moderate to good effects as antiproliferative, [17] antioxidant, [18] and anticancer agent.…”

“…In a pursuit to discover more compounds targeting this ailment, a series of innovative N-aryl 2-{[5-(naphthalen-1ylmethyl)-4-ethyl-4H-1,2,4-triazol-3-yl]thio}acetamide derivatives were synthesized using a procedure reminiscent of our previous work. [7] These derivatives originate from 5-(naphthalen-1ylmethyl)-4-ethyl-4H-1,2,4-triazole-3-thione/thiol, which stems from the initial synthesis of 2-(naphthalen-1-yl)acetohydrazide, itself derived from 2-(naphthalen-1-yl)acetic acid. The synthesized acetamide compounds underwent assessment for αglucosidase inhibitory activity.…”

“…Spectral data and X-ray diffraction emphasized the superior stability of 5-(naphthalen-1-ylmethyl)-4-ethyl-4H-1,2,4-triazole-3thione in its solid state, in stark contrast to its tautomeric thiol form, aligning with the behavior of the previously reported compound 5-(naphthalen-1-ylmethyl)-4-phenyl-4H-1,2,4triazole-3-thione. [7] The use of molecular docking shed light on the interaction between the agent and the target protein, revealing a robust correlation with the scrutinized α-glucosidase inhibitory activity.…”