Synthesis of 1,2,3-Triazole Derivatives and in Vitro Antifungal Evaluation on Candida Strains

Abstract

1,2,3-Triazoles have been extensively studied as compounds possessing important biological activities. In this work, we describe the synthesis of ten 2-(1-aryl-1H-1,2,3-triazol-4-yl)propan-2-ols via copper catalyzed azide alkyne cycloaddition (CuAAc or click chemistry). Next the in vitro antifungal activity of these ten compounds was evaluated using the microdilution broth method against 42 isolates of four different Candida species. Among all tested compounds, the halogen substituted triazole 2-[1-(4-chlorophenyl)-1H-(1,2,3)triazol-4-yl]propan-2-ol, revealed the best antifungal profile, showing that further modifications could be done in the structure to obtain a better drug candidate in the future.

Design, Synthesis and Antifungal Activity of Novel Benzofuran-Triazole Hybrids

“…Finally, employing click chemistry, compounds 2a,b were cyclized with 3a-i, respectively, to give target compounds 4a-r in good yields. In recent years, the 1,2,3-triazole scaffold became a highlight fragment with the emergence of click chemistry and the 1,2,3-triazole-containing compounds were reported to possess a variety of biological activities [24][25][26][27][28], especially as antifungal agents [29][30][31]. Furthermore, the hybridizations of the 1,2,3-triazole moiety with other antifungal agents were reported.…”

“…Alkylation of the hydroxyl group of 1a,b wi yl bromide gave terminal alkyne derivatives (2a,b). The aromatic azides (3a-i) were prepar corresponding anilines following the Sandmeyer conditions [27,31]. Finally, employing cli y, compounds 2a,b were cyclized with 3a-i, respectively, to give target compounds 4a-r lds.…”

“…Among them, benzofuran inhibitors showed high selectivity and powerful antifungal activity [16][17][18][19] (Figure 1). Furthermore, the benzofuran core itself possessed a definite antifungal activity and numbers of benzofuran derivatives were reported without indicating the targets [20][21][22][23] In recent years, the 1,2,3-triazole scaffold became a highlight fragment with the emergence of click chemistry and the 1,2,3-triazole-containing compounds were reported to possess a variety of biological activities [24][25][26][27][28], especially as antifungal agents [29][30][31]. Furthermore, the hybridizations of the 1,2,3-triazole moiety with other antifungal agents were reported.…”

New 1,2,3-Triazole Containing PolyestersviaClick Step-Growth Polymerization and Nanoparticles Made of Them

“…Due to the high reaction rates and quantitative yields, high-molecularweights can be achieved. It is important to note that CuAAC click reaction results in the formation of 1,2,3-triazole ring which is known as low toxic moiety [14,15]. Furthermore, triazole rings-containing compounds display a broad spectrum of biological activities, including antimicrobial, antiviral, antifungal, anticancer, anti-inflammatory, antitubercular, antioxidant, analgesic, and antimalarial activities [16,17].…”

Ruthenium-Free Preparation of 1,5-Disubstituted Triazoles by Alkylative Debenzylation of 1,4-Disubstituted Triazoles

“…Although relatively unreactive, substituted 1,2,3-triazoles, available through inexpensive copper-catalysed 'click' cycloaddition (CuAAC) reactions, are of value in a wide variety of research fields, including materials science 4 and synthetic chemistry, 5 as a ligating moiety in organometallic chemistry, 6 for cyclopropanation chemistry, 7 and as a pharmacophore in medicinal chemistry; 8 they possess a range of biological activities, including antifungal, 9 antibody, 10 anti-cancer, 11 anti- Alzheimer's, 12 and anti-HIV activities. When converted into triazolium salts, they provide an important class of ionic liquids.…”