Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety

Abstract

BackgroundPlant fungi (e.g., Pellicularia sasakii, Gibberella zeae, Fusarium oxysporum, and Cytospora mandshurica and Phytophthora infestans) and bacteria (e.g., Ralstonia solanacearum) are extremely difficult to manage in agricultural production. The high incidence of plant mortality and the lack of effective control methods make P. sasakii and R. solanacearum two of the world’s most destructive plant pathogens. Pathogenic fungi and bacteria are responsible for billions of dollars in economic losses worldwide each year. Thus, we designed an active amide structure and synthesized a series of novel amide derivatives containing a triazole moiety to discover new bioactive molecules and pesticides that can act against fungi and bacteria.ResultsA series of amide derivatives containing a triazole moiety were synthesized. All the obtained compounds were characterized through proton and carbon nuclear magnetic resonance spectroscopy, infrared spectroscopy, and elemental analysis. Preliminary antifungal activity test showed that some of the synthesized compounds exhibited moderate antifungal activity against P. sasakii, G. azeae, F. oxysporum, C. mandshurica, and P. infestans at 50 mg/L. Compound 4u displayed more potent antifungal activity against P. sasakii and G. azeae than hymexazol. Preliminary antibacterial activity results showed that some of the synthesized compounds exhibited high anti-bacterial activity against R. solanacearum at 200 mg/L. Compounds 4m and 4q displayed high antibacterial activity against R. solanacearum, with 71% and 65% inhibitory rates, respectively.ConclusionsA series of novel amide derivatives containing 1,2,4-triazole moiety were synthesized through the reaction of intermediate 3 with different acyl chlorides and anhydrous potassium carbonates in anhydrous tetrahydrofuran at 50°C, using 2,4-dichloroacetophenoneas as a starting material. The title compounds exhibited high inhibitory effects against P. sasakii, R. solanacearum, and G. azeae.

Synthesis and in Silico Analysis of Novel 1,2,4- Triazolylamides as Potential Antifungals

“…Among aniline derivatives (3a, 4a, 5a; 3b, 4b, 5b; 3c, 4c, 5c; 3d, 4d, 5d) the fluoro substitution in the rings had positive influence on the antifungal activity 9,11 of the compounds and these results were also in consonance with the lipophilicity factor. The similar results favouring the fluorination in the molecule were reported by Tang and co-workers who reported fluorine substituted amidotriazoles with favourable activites 22 . Presence of pyridine ring did not induce favourable inhibition of the germination of the fungal spores.…”

CAN catalyzed one-pot synthesis and docking study of some novel substituted imidazole coupled 1,2,4-triazole-5-carboxylic acids as antifungal agents

“…Thus, the high therapeutic properties of the imidazole related drugs have encouraged the medicinal chemists to synthesize a large number of novel chemotherapeutic agents. 1, 2, 4-Triazole ring has drawn great attention to medicinal chemists due to its wide variety of activities including antibacterial [16][17][18] and antifungal [19][20][21][22], anticancer [23,24] and antioxidant [25,26]. These two heterocyclic moities are important core for antifungal activity.…”

Synthesis, structure and properties of N-R-amides and hydrazides of 2-[4-R-5-(theophylline-7ʹ-yl)-1,2,4-triazole-3-ylthio]acetic acid

“…The derivatives of 1,2,4-triazole-3-thiol and theophylline are a very promising class of chemical compounds for the synthesis of biologically active compounds based on them, due to the wide spectrum of biological activity of these heterocycles' derivatives [2][3][4][5][6][7]10]. Objective reasons for the search for a number of 1,2,4-triazol-3-thiol and theophylline derivatives are the high synthetic and pharmacological potential of these synthones [2,5,7,10]. Our attention was drawn to previously unexplored amides and 2-[4-R-5-(theophylline-7'-yl)-1,2,4-triazole-3-ylthio]acetic acid.…”