Synthesis and Antifungal Activity of Novel Myrtenal-Based 4-Methyl-1,2,4-triazole-thioethers

Abstract

A series of novel myrtenal derivatives bearing 1,2,4-triazole moiety were designed and synthesized by multi-step reactions in an attempt to develop potent antifungal agents. Their structures were confirmed by using UV-vis, FTIR, NMR, and ESI-MS analysis. Antifungal activity of the target compounds was preliminarily evaluated by the in vitro method against Fusarium oxysporum f. sp. cucumerinum, Physalospora piricola, Alternaria solani, Cercospora arachidicola, and Gibberella zeae at 50 µg/mL. Compounds 6c (R = i-Pr), 6l (R = o-NO2 Bn), and 6a (R = Et) exhibited excellent antifungal activity against P. piricola with inhibition rates of 98.2%, 96.4%, and 90.7%, respectively, showing better or comparable antifungal activity than that of the commercial fungicide azoxystrobin with a 96.0% inhibition rate, which served as a positive control.

Synthesis and Antifungal Activity of Novel 3-Caren-5-One Oxime Esters

“…For example, a series of 3-ethoxy-4-hydroxybenzaldehyde oxime esters were synthesized and evaluated for their in vitro antifungal activity against three pathogenic fungi and antibacterial activity against three bacterial strains, and the structure-activity relationship was also preliminarily summarized [ 26 ]. In continuation of our interest in the bioactive properties of natural product-based compounds [ 27 , 28 , 29 , 30 , 31 , 32 , 33 ], a series of novel 3-caren-5-one oxime esters were designed and synthesized by integrating bioactive oxime esters into the skeleton of 3-carene. Structural characterization and antifungal evaluation of all the title compounds were carried out as well.…”

Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

“…1,2,4-Triazole derivatives are antimicrobial, antifungal, antitumor, anti-inflammatory, antituberculosis, and herbicidal properties [ 61 , 62 , 63 ]. A series of novel myrtenal-based 4-methyl-1,2,4-triazole-thioethers were synthesized by Duan and co-workers and tested as antifungal agents [ 64 ]. Antifungal activities of these compounds were evaluated by the in vitro method against Fusarium wilt on cucumber ( Fusarium oxysporum f. sp.…”

Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety

“…Due to their diverse pharmacological properties, 1,2,4-triazole derivatives have been extensively studied for application in the fields of medicine and agrochemicals. Besides antimicrobial [10,11], anti-inflammatory [10,12], antituberculosis [13], antifungal [14], and herbicidal properties [15], antitumor activity has been reported [16], e.g., in the anticancer drugs letrozole, anastrozole, and vorozole [17]. Meanwhile, more and more new 1,2,4-triazole anticancer compounds are being studied [18,19].…”