Pyrrolo[1,2-a]azepines Coupled with Benzothiazole and Fluorinated Aryl Thiourea Scaffolds as Promising Antioxidant and Anticancer Agents

Abstract

Background: Cancer remains a major health concern throughout history and is responsible for huge numbers of deaths globally. The sensitivity of cancer cells to anticancer drugs is a crucial factor for developing effective treatments. Methods: Pyrrolo[1,2-a]azepines coupled with benzothiazole and fluorinated aryl thiourea scaffolds have been synthesized, and their potential as cytotoxic agents was investigated against different cancer cell lines such as human ovarian cancer (SK-OV-3), cervical cancer (HeLa), colon adenocarcinoma (HT-29) and non-small-cell lung carcinoma (A549). Cytotoxicity of new compounds was confirmed using SRB assay against non-cancer MDCK cell line. In addition, free radical scavenging activity of new pyrrolo[1,2-a]azepines was examined by adopting DPPH and ABTS assays. Results: The results concluded that the presence and position of fluorine atom(s) on the thiourea unit played a significant role in order to gain anticipated efficacies. Results of the cytotoxic assay against non-cancer MDCK cells showed that these new derivatives are safe to study further. New structures were confirmed using spectral and elemental analyses. Conclusion: Pyrrolo[1,2-a]azepines endowed with a benzothiazole entity and fluorinated aryl thiourea substituents were derived aiming to furnish remarkable antioxidant and anticancer activities. New molecules generated showed interesting biological result correlated with the structure and substituent of the final derivatives. Specifically, numbers and position of fluorine atoms on the thiourea unit influenced the biological profile of the mentioned compounds.