The solvent‐free synthesis of polysubstituted pyrroles by a reusable copper Schiff base complex immobilized on silica coated Fe₃O₄, and DNA binding study of one resulting derivative as a potential anticancer drug

Abstract

We demonstrate herein the synthesis of a new copper Schiff base complex immobilized on silica‐coated Fe3O4 nanoparticles. The structure and composition of this magnetic nanocatalyst were analyzed using Fourier transform infrared (FT‐IR), X‐ray powder diffraction (XRD), vibrating sample magnetometry (VSM), scanning electron microscopy (SEM), energy dispersive X‐ray (EDX) and inductively coupled plasma atomic emission spectroscopy (ICP‐AES). This nanocomposite was found to be an efficient nanocatalyst for the synthesis of polysubstituted pyrrole derivatives and the products were isolated with high turnover number (TON) and high to excellent yields. Among the new synthesized polysubstituted pyrrole derivatives, we explored the first computational and experimental binding study of methyl 1‐benzyl‐4‐(furan‐2‐yl)‐2‐methyl‐1H‐pyrrole‐3‐carboxylate (SP‐10) with calf thymus deoxyribonucleic acid (ct‐DNA), suggesting their application as potential anticancer activity. In addition, the binding modes of SP‐10 with DNA and human serum albumin (HSA) were verified by molecular docking technique.

Review on synthesis of pyrrole derivatives promoted by nanoparticles

“…Recovery and reusability of the nanocatalyst were performed 10 times without considerable loss in its activity. [77] In 2018, Salehzadeh and co-workers reported synthesis of polysubstituted pyrroles using copper Schiff base complex immobilized on silica-coated the MNPs has shown peaks at 2θ = 18.3 , 30.5 , 35.9 , 43.3 , 53 , 57 , 62 , and 74.5 , and these peaks confirmed the structure of the nanoparticles. The SEM images confirmed the spherical shape with the size diameter 20 nm of the nanoparticles.…”

Application of β‐Nitrostyrene in Multicomponent Reactions for the Synthesis of Pyrrole Derivatives

“…Four‐component reaction of primary amines (1 mmol), aldehydes (1 mmol), ethyl acetoacetate (1 mmol) and nitromethane (1 mmol) in the presence of various amount of Fe 3 O 4 @SiO 2 @CuSB nanocatalyst in different solvents such as H 2 O, EtOH, CH 3 CN, CH 2 Cl 2 , toluene, n ‐hexane and solvent‐free conditions at different temperatures was investigated that the best yield was obtained using (0.06 g) of catalyst under solvent‐free condition at room temperature (Scheme ). Recovery and reusability of the nanocatalyst was performed for the ten times without considerable loss in its activity …”

Catalyst‐free one‐pot three‐component rapid synthesis of polysubstituted pyrroles by liquid‐assisted grinding

“…Polysubstituted pyrroles, an important class of heterocyclic compounds, have received considerable interest due to their important biological and pharmacological activities, such as anticancer [1,2], anti‐inflammatory [3,4], anti‐HIV [5], antimicrobial [6,7], neuroprotective [8] activities (Figure 1). Many marketed drugs, such as atorvastatin, sunitinib, netropsin, vonoprazan, also contain structural motifs of polysubstituted pyrroles [9–12].…”