Silica‐tethered cuprous acetophenone thiosemicarbazone (STCATSC) as a novel hybrid nano‐catalyst for highly efficient synthesis of new 1,2,3‐triazolyl‐based metronidazole hybrid analogues having potent antigiardial activity

Abstract

The preparation, characterization and application of silica‐tethered cuprous acetophenone thiosemicarbazone (STCATSC) as a novel hybrid nano catalyst for synthesis of new 1,2,3‐triazolyl‐based metronidazole hybrid analogues is described. STCATSC 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), FT‐IR and inductively coupled plasma (ICP) analysis. This catalyst is used to prepare the new 1,2,3‐triazolyl‐based metronidazole hybrid analogues. The ‘Click’ Huisgen cycloaddition reaction of 2‐methyl‐5‐nitro‐1‐prop‐2‐ynyl‐1H‐imidazole with diverse β‐azidoalcohols in a THF‐water media at R.T. provides the products in good to excellent yields using STCATSC. STCATSC is proved to be a stable, low cost, reusable and environmentally benign hybrid catalyst. Products are in vitro tested against Giardia lamblia (G. lamblia) in which determined that all compounds exhibit varied promising antigiardial activity compare to metronidazole as a reference drug. Among the products, 1‐(4‐((2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl)‐1H‐1,2,3‐triazol‐1‐yl)‐3‐phenethoxypropan‐2‐ol and 1‐(4‐((2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl)‐1H‐1,2,3‐triazol‐1‐yl)‐3‐(3‐phenylpropoxy)propan‐2‐ol are demonstrated to exhibit the potent antigiardial activity even stronger than metronidazole.

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

“…In continuation of our interests and also ongoing researches in the field of copper heterogeneous nano-catalysts and also design and synthesis of new 1,2,3-triazolyl conjugate compounds [26][27][28][29][30], hereby, we would like to report the synthesis and characterization of hydroxyapatite silica propyl bis aminoethoxy ethane cuprous complex (HASPBAEECC) as a novel hybrid nano-catalyst for the synthesis of new benzimidazole-1,2,3-triazole hybrid analogues as antifungal agents 11 (Fig. 2).…”

“…After synthesis and characterization of the catalyst, the synthesis of title compounds was conducted due to Scheme 2. As shown in Scheme 2, initially, the propargyl alcohol ( 12) was tosylated utilizing tosyl chloride due to our improved procedure [26]. Application of propargyl tosylate ( 13) is much better than propargyl bromide since the propargyl bromide beside its extensive risks, hazards and expensiveness is not available in its pure forms [33].…”

New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches

“…MoO 3 -nanoparticles were previously synthesized [ 26 , 48 ]. For identification of nanostructure powder X-ray diffraction (PXRD) and scanning electron microscopy (SEM) analysis were carried out.…”

Effects of repeat unit charge density on the physical and electrochemical properties of novel heterocationic poly(ionic liquid)s

“…Propargyl tosylate was prepared by the reaction of tosyl chloride with an excess of propargyl alcohol in accordance with the well-established procedure. 63 Ionic liquid monomers (ILMs) N,N-dimethyl-N,N-dipropargylammonium bis(trifluoromethylsulfonyl)imide (1) and N,N-dibutyl-N,N-dipropargylammonium bis(trifluoromethylsulfonyl)imide (2) were synthesized as described previously. 42…”