A New Strategy for the Synthesis of Porphyrin and Expanded Porphyrin Derivatives from Di- and Tripyrromethanes: Antioxidant, Cytotoxic Activity, and Molecular Docking Evaluation

Abstract

We present a novel and effective process for producing porphyrins in the absence of a solvent condition, in contrast to earlier procedures. An aldehyde and pyrrole were condensed by grinding in the presence of an acidic catalyst during the synthetic process. By adjusting reactant molar ratios and concentrations, dipyrromethane 3 and tripyrromethane 4 derivatives, the synthesis was improved at room temperature in 5–10 minutes with excellent yields. In this work, we successfully synthesized a number of novel porphyrin derivatives, 6 b–j. Here, we describe a method for reacting dipyrromethane 3a with various aryl aldehydes 5 b–j while using DMF as a capping agent. Moreover, expanding porphyrin derivatives 7 a, and 7 b were synthesized from the reaction of 4a with aldehydes 5a and 5b at 0 °C. Porphyrin derivatives 6 g and 6 h displayed good antioxidant potential. The cytotoxic activity of compounds 6 h, 6 b, and 6c against the human cell lines HePG-2 and MCF-7 were studied. The binding modes of the synthesized compounds were analyzed by docking studies that showed good binding scores against the diverse amino acids of the selected proteins (Bcl-2). The conducted docking studies were found to be consistent with cytotoxic results.