Synthesis and Biological Activity of Novel 1‐Substituted Phenyl‐4‐[N‐[(2′‐morpholinothoxy)phenyl]aminomethyl]‐1H‐1,2,3‐Triazoles

Abstract

In an attempt to search for potent antifungal agents, a series of novel 1-substituted phenyl-4-[N-[(2'-morpholinothoxy)phenyl]aminomethyl]-1H-1,2,3-triazoles 5a-m was designed and synthesized via Huisgen cycloaddition reaction between various (2-morpholinoethoxy)-N-(prop-2-ynyl)aniline and different azidobenzene. Their chemical structures were characterized by (1) H NMR and elemental analysis. A cleaner reaction with milder conditions and satisfactory yields was observed in the micorwave-assisted synthesis of 4a-c. The fungicidal activity of some target compounds were evaluated in vitro against Fusarium omysporum, Physalospora piricola, Alternaria solani, Cercospora arachidicola and Gibberella zeae at 50 μg/mL. The bioassay results indicated that some compounds exhibited moderate fungicidal activities. Furthermore, compound 5h displayed equal activity to the positive control compounds against Alternaria solani.

Design and Synthesis of Benzoxepine–Based 1,2,3‐Triazoles: Molecular Docking and in vitro Antimicrobial Activity Evaluation

“…1,2,3‐Triazoles have been attracting the interest of medicinal chemists and organic chemists for new drugs development owing to their broad spectrum of biological activities, including anticancer, [4] antibacterial, [5] antifungal, [6] antiviral, [7] anti–HIV, [8] anti–tubercular, [9] antiproliferative, [10] anticonvulsant, [11] anti–inflammatory, [12] antimalarial, [13] antineoplastic, [14] insecticides, alpha‐glycosidase inhibitory, [15] antioxidant, [16] and antidiabetic [17] . Recently, agrochemical potential of 1,2,3‐triazoles has also aroused significance and some of them have been proved to possess moderate anti‐phytopathogenic bioactivities [18] . On the other hand, Benzoxazepines represent a key motif in heterocyclic chemistry and occupy an important place in medicinal chemistry, nucleic acids, hormones and therapeutic drugs [19] .…”

“…[17] Recently, agrochemical potential of 1,2,3-tria-zoles has also aroused significance and some of them have been proved to possess moderate anti-phytopathogenic bioactivities. [18] On the other hand, Benzoxazepines represent a key motif in heterocyclic chemistry and occupy an important place in medicinal chemistry, nucleic acids, hormones and therapeutic drugs. [19] These derivatives are well-known pharmacophores showing capable properties against various diseases such as central nervous system damage, [20] antipsychotic, [21] anti-HIV, [22] tranquilizing, [23] and anticancer activities.…”