Synthesis and antimicrobial potential of nitrofuran–triazole congeners

Abstract

A series of 5-nitrofuran-triazole congeners were designed and synthesized by carrying out suitable structural modifications of the previously reported counterparts and were evaluated for their antimicrobial potential against both Gram-positive and Gram-negative bacterial strains. The compounds exhibited promising inhibition towards different Gram-positive pathogenic strains, while mild inhibitory effects were observed towards Gram-negative bacterial strains. Some of the compounds 9f, 9g, 9l and 9m were most active among the series, exhibiting a MIC value of 1.9 μg mL(-1) against different bacterial strains. The bactericidal activity was found to be in coherence with the bacterial growth inhibition data. The compounds were tested against fourteen different fungal strains and were found to possess excellent antifungal activities. Interestingly, all the compounds were equipotent to miconazole against one or more of the tested fungal strains and showed good activity against the other counterparts. A similar trend was observed in the case of their minimum fungicidal concentration values. Moreover, compound 9f exhibited two fold superior antifungal activity (MIC = 3.9 μg mL(-1)) than the standard miconazole (MIC = 7.8 μg mL(-1)) against C. albicans and C. parapsilosis. These compounds also effectively inhibited biofilm formation and compound 9f exhibited excellent anti-biofilm activity demonstrating a biofilm inhibitory concentration (BIC) as low as 0.8 μg mL(-1). A brief mechanistic study carried out on the most effective conjugate 9f indicated that it inhibits the ergosterol biosynthesis, thereby exhibiting antifungal effects. Molecular modelling studies carried out to study the binding modes of 9f correlates well with the antifungal activity and supported by ergosterol biosynthesis inhibition assay data. Most of these compounds exhibited ten times lower cytotoxicity toward the normal cells compared to the antimicrobial activity.

Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5‐disubstituted isoxazole compounds based on 5‐nitrofuran scaffolds

“…In this family, it is important to highlight the compounds based on the 5‐nitrofurans structures, such as nitrofurazone 9 and its hydroxylated derivative 10 , with potent antichagasic activity; nifurtimox 11 , a drug used to treat Chagas disease; and nifuroxazide 12 , a nitrofuran with potent antimicrobial and antiprotozoal activity (Figure ) . Recently, Kamal et al synthesized a 5‐nitrofuran–triazole congener 13 with antifungal properties, extending the antimicrobial activities of this scaffold.…”

Contact Active Antimicrobial Coatings Prepared by Polymer Blending

“…[1] Biofilms represent communal structures of microorganisms encased in robust and 1,2,3-triazole side-chain groups, which demonstrated considerable antimicrobial activity against Gram-negative and Gram-positive bacteria and fungi. In addition, it was previously reported the potential of systems containing 1,2,3-triazol groups for biofilm inhibition, [19,20] thus these polymers can be attractive candidates to prepare antimicrobial surfaces by blending process. The hydrophobic/hydrophilic balance, the length of the alkyl chain as well as the flexibility of the polymers are factors that also importantly affect the antimicrobial efficiency.…”

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.…”

“…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.…”