Natural‐Antioxidant‐Inspired Benzo[b]selenophenes: Synthesis, Redox Properties, and Antiproliferative Activity. Issue 13 (7th June 2016)

• Record Type: Journal Article
• Authors: Paegle, Edgars; Domracheva, Ilona; Turovska, Baiba; Petrova, Marina; Kanepe‐Lapsa, Iveta; Gulbe, Anita; Liepinsh, Edvards; Arsenyan, Pavel
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 13(2016)
• Page Start: 1929
• Page End: 1938
• Publication Date: 2016-06-07
• Subjects: antiproliferative activity -- cytotoxicity -- radicals -- redox chemistry -- selenophenes; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201600472
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: The cyclization of arylalkynes under selenobromination conditions, combined with an acid‐induced 3, 2‐aryl shift, was elaborated as a general synthetic pathway for the preparation of polyhydroxy‐2‐ and ‐3‐arylbenzo[ b ]selenophenes from the same starting materials. The redox properties, free‐radical‐scavenging ability, and cytotoxicity against malignant cell lines (MCF‐7, MDA‐MB‐231, HepG2, and 4T1) of the synthesized compounds were explored, and the obtained results were used to consider the structure–activity relationships (SARs) in these compounds. Consequently, the structural features that were responsible for the highly potent peroxyl‐radical‐scavenging activity were established. Abstract : Don′t worry, [ b ] happy : Arylalkyne cyclization under selenobromination conditions with an acid‐induced 3, 2‐aryl shift afforded polyhydroxybenzo[ b ]selenophenes. Their redox properties, free‐radical‐scavenging ability, and cytotoxicity are reported.