Synthesis Of Model Compounds Of Superoxide Dismutase And Their Chemical Simulation

Superoxide radical anion (O2- ) is an active species generated during biological oxidation utilizing molecular oxygen. It is involved in several important biological processes. High level of O2- may cause cell damage leading to the appearance of several diseases. It was reported that in human body O2- is related to the occurrence of such abnormities as aging, cancer, diabetes, mental disorder and arthritis. Superoxide dismutase (SOD) is a metal enzyme found in animals, plants and microorganisms. SOD catalyzes the conversion of Superoxide radical anion to hydrogen peroxide (H2O2) and oxygen, thus reducing its body content. Commercial SOD products come from animal blood extracts and are expensive due to the high cost related to tedious extraction and preparation. In addition, its lifetime in human body is only a few hours. Its widespread application is further limited by its poor cell permeability due to the large size of SOD. Therefore, chemical synthesis of SOD mimics has attracted the attention of many chemists. SOD mimics hold great potential as pharmaceutical agents for the treatment of many diseases.Calixpyrroles are a class of nitrogen-containing microcyclic compounds. These molecules can be used as hosts for the formation of inclusion compounds with neutral and anionic molecules as well as metal complexes. Calixpyrroles have become important targets of synthetic organic chemists due to their potential application in many areas such as molecular recognition, molecular self-assembly and supermolecular catalysis.We have been involved in the synthesis and metal coordination chemistry of porphyrins, Calixpyrroles and calixfurans. These molecules are screened as potential model compounds of SOD.This research project is focused on the improved and new synthesis of Calixpyrroles. First, improved synthesis of ten carbonyl compounds was developed. Second, eleven Calixpyrroles, including these which have not been reported previously, were successfully synthesized by optimizing various reaction conditions including reaction media and catalysts. Finally, two porphyrins have been synthesized and their metal complexes prepared.