Synthesis of fish scale derived hydroxyapatite silica propyl bis aminoethoxy ethane cuprous complex (HASPBAEECC) as a novel hybrid nano-catalyst for highly efficient synthesis of new benzimidazole-1,2,3-triazole hybrid analogues as antifungal agents

Abstract

The preparation, characterization and application of hydroxyapatite silica propyl bis aminoethoxy ethane cuprous complex (HASPBAEECC) as a novel hybrid nano-catalyst for synthesis of new benzimidazole-1,2,3-triazole hybrid analogues as promising antifungal agents have been described. HASPBAEECC is fully characterized by different microscopic, spectroscopic and physical techniques, including scanning electron microscopy (SEM), transmission, X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDS), thermogravimetric analysis (TGA) and FT-IR. The ʻClick̕ Huisgen cycloaddition reaction of N-propargyl benzimidazole with diverse azidoalkyls in a THF-water media at ambient temperature provides the products in good-to-excellent yields using HASPBAEECC. HASPBAEECC is proved to be a stable, low cost, reusable and environmentally benign nanohybrid catalyst. The target compounds were screened against some pathogenic fungal comprising Candida albicans, Candida krusei, Candida parapsilosis, Aspergillus fumigatus and Aspergillus flavus in which it was determined that compounds 11f and 11 h have displayed promising antifungal activity similar to fluconazole as a reference drug.

Click chemistry beyond metal‐catalyzed cycloaddition as a remarkable tool for green chemical synthesis of antifungal medications

“…Benzimidazole-1,2, 3-triazole hybrids were synthesized by the azide-alkyne Huisgen cycloaddition reaction of N-propargyl benzimidazole with diverse azidoalkyls in the presence of a nanocatalyst (HASPBAEECC). Screening of these hybrids against some pathogenic fungal strains identified compounds N′1 and N′2 as promising antifungal agents with similar activity to fluconazole against A. fumigatus and A. flavus (MIC = 2 μg mL −1 ) and better than fluconazole (MIC = 64 μg mL −1 ) against C. krusei with the MIC values of 32 μg mL −1 (Soltani Rad et al, 2022). Using the click reaction, Al-Ghulikah et al ( 2023) synthesized a set of 1,2,3 -triazole-benzimidazolidinone hybrid derivatives from a reaction between a terminal alkyne-containing benzimidazolidinone moiety and various aryl azides reacted.…”

Click chemistry: A fascinating, Nobel-winning method for the improvement of biological activity

“…Although synthetically derived those compounds containing 1,2,3-triazole group have various biological activities such as anticancer [41][42][43][44] , antibacterial [45,46] , antifungal [47,48] , anti-HIV [49,50] , antituberculosis [51,52] , antioxidant [53,54] , antiproliferative [55,56] and enzyme inhibitory [57,58] , these compounds are not found in nature. Therefore, the importance of these compounds in medicinal chemistry field has become undeniable, and so 1,2,3-triazole groups have been described as a "pharmacophore group" with the meaning of the main functional group responsible for the effect of a drug compound and the synthesis of the related compound has been carried out by many scientists after that time [59] .…”

Functionalization of Fe3O4@SiO2 nanoparticles with Cu(i)-thiosemicarbazone complex as a robust and efficient heterogeneous nanocatalyst for N-arylation of N-heterocycles with aryl halides

“…Hence, there is still ongoing interest in preparing and applying such catalysts having broader applicability for Ullmann-type N-arylation of N-heterocycles. To this end and in pursuit of our research interest on copper-catalyzed C-N bond coupling reactions, [39][40][41][42] herein we introduce the functionalized silicacoated magnetite nanoparticles with Cu(I)-thiosemicarbazone complex (Fe 3 O 4 @SiO 2 -[CuL]) as a new magnetically recoverable nano catalyst for Ullmann-type Narylation of nucleobases, xanthines, and other N-heterocycles with aryl halides in DMF at 110 °C (Scheme 1).…”