Abstract
Finding novel cholinesterase inhibitors that would be able to cross the blood--brain barrier, have favorable pharmacokinetic parameters, and reduce hepatotoxicity along with other side effects has been the main focus of investigations dealing with Alzheimer disease. In this study we evaluated cholinesterase inhibitory and antioxidant activity of seven oxazole derivatives. These compounds have been efficiently and sustainably prepared by photochemical electrocyclization reaction. Various naphthoxazoles have been previously investigated as potential antibacterial, antituberculosis, and anticancer agents. They have also been tested for antioxidant activity, but never for cholinesterase inhibitory activity. Among the tested oxazole derivatives, fused heterobenzoxazole compounds with pyridine and thiophene moiety, oxazolo[5,4-$h$]isoquinoline, thieno[2',3':5,6]benzo[1,2-$d$]oxazole, and thieno[3',2':5,6]benzo[1,2-$d$]oxazole, showed the greatest potential for both cholinesterase inhibitory and antioxidant activity. Among them, thieno[2',3':5,6]benzo[1,2-$d$]oxazole was found to be the best one.
Highlights
Aerobic metabolic processes produce reactive oxygen species and free radicals that accumulate in cells on a daily basis
These oxygen species and free radicals affect different organs and systems in our body and are usually controlled via internal antioxidants as well as antioxidant enzymes and enzyme systems. 1,2 Uncontrolled production of these species leads to attacks on various biomolecules such as lipids, proteins, and DNA, as well as on cellular machinery and membranes, causing oxidative stress
ŠAGUD et al./Turk J Chem synthetic approaches were developed and the oxazole nuclei became an important building block for the synthesis of many biologically active molecules. 10−24 Some of the fused polycyclic compounds with oxazole rings have shown antibacterial and antituberculosis activities as well as anticancer activity and some have been tested for antioxidant activity. 25−28 New efficient methodology for the preparation of oxazole derivatives provides a valuable tool to the organic chemist
Summary
Aerobic metabolic processes produce reactive oxygen species and free radicals that accumulate in cells on a daily basis. Seven in-house synthesized compounds, naphthoxazoles [1,2,3] and fused heterobenzoxazoles (4–7, Figure), were tested for their antioxidant activity, using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and ferric reducing antioxidant power (FRAP) methods. There is an earlier example of a hydroxyl radical scavenging study of naphthoxazole compounds, performed by Wang et al 28 In that study the antioxidant activities of naphtho[2,1d ]oxazoles bearing an acetyloxymethyl group on position 2 of the oxazole ring were tested.
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