Design and stereoselective synthesis of novel β-lactone and β-lactams as potent anticancer agents on breast cancer cells. Issue 8 (22nd February 2018)

• Record Type: Journal Article
• Authors: Rashidi, Mahnoosh; Islami, Mohammad Reza; Esmaeili-Mahani, Saeed
• Is Part Of: Tetrahedron. Volume 74:Issue 8(2018)
• Page Start: 835
• Page End: 841
• Publication Date: 2018-02-22
• Subjects: β-lactam -- β-Lactone -- 2, 4-Dichlorophenoxyacetic acid -- Ketene -- Anticancer; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.12.044
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: To produce a novel class of anticancer compounds, an efficient method for synthesizing novel β-lactone and β-lactam frameworks was developed based on the reaction of a new ketene with C=O and C=N bonds. Functionalized 2-azetidinones were efficiently synthesized by employing 2, 4-dichlorophenoxylketene, which was generated in situ. The reaction of the ketene with aldehydes was not successful and in all cases except for 4-nitrobenzaldehyde, a rearranged dimer of the ketene was obtained as a lactone. Anticancer cellular activity of all new β-lactams and lactones on breast cancer cells was studied. All new synthesized compounds exhibited potential anticancer activity which may guarantee their future application in moderate chemotherapy. Graphical abstract: