Related Experiment Video
Updated: May 2, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Synthesis and Antifungal Activity of 4-Arylamino-1,2-Naphthoquinones-1,2,3-Triazoles Hybrids
Acácio Silva de Souza1, Gabriel Nogueira da Silva1, Iva Souza de Jesus1
1Faculty of Pharmacy, Federal Fluminense University, Niterói, Brazil.
Abstract:
Quinones have been strategically combined with various heterocyclic scaffolds to enhance their biological properties. In this study, two new series of hybrid derivatives of 4-amino-1,2-naphthoquinones bearing a triazole ring were synthesized via a three-step procedure. These compounds were evaluated for antifungal activity and for their ability to generate reactive oxygen species (ROS). The compounds were active against both yeast and filamentous fungi. Notably, their antifungal effect was not linked to ROS generation or to interaction with lanosterol 14α-demethylase, the main accepted mechanisms of action for naphthoquinones and triazoles, respectively. The structural diversity of these 1,2-naphthoquinones enables a range of molecular interactions with fungal targets, making them promising candidates for developing novel antifungal agents, particularly given the high prevalence of fungal infections in human colonization and their clinical significance.
Related Concept Videos
Antifungal Agents
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diazonium Group Substitution: –OH and –H
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...

