title: Natural-Antioxidant-Inspired Benzo[b]selenophenes: Synthesis, Redox Properties, and Antiproliferative Activity.
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.
authors.affiliation: Department of Medicinal Chemistry, Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia.
authors.forename: Edgars
authors.initials: E
authors.lastname: Paegle
authors.affiliation: Department of Medicinal Chemistry, Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia.
authors.forename: Ilona
authors.initials: I
authors.lastname: Domracheva
authors.affiliation: Department of Medicinal Chemistry, Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia.
authors.forename: Baiba
authors.initials: B
authors.lastname: Turovska
authors.affiliation: Department of Medicinal Chemistry, Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia.
authors.forename: Marina
authors.initials: M
authors.lastname: Petrova
authors.affiliation: Department of Medicinal Chemistry, Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia.
authors.forename: Iveta
authors.initials: I
authors.lastname: Kanepe-Lapsa
authors.affiliation: Department of Medicinal Chemistry, Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia.
authors.forename: Anita
authors.initials: A
authors.lastname: Gulbe
authors.affiliation: Department of Medicinal Chemistry, Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia.
authors.forename: Edvards
authors.initials: E
authors.lastname: Liepinsh
authors.affiliation: Department of Medicinal Chemistry, Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia. pavel.arsenyan@lycos.com.
authors.forename: Pavel
authors.initials: P
authors.lastname: Arsenyan
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003500:Cyclization; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010084:Oxidation-Reduction / Q000187:drug effects
chemical_list: D000970:Antineoplastic Agents; D000975:Antioxidants; D001555:Benzene Derivatives; D016566:Organoselenium Compounds
keywords: antiproliferative activity; cytotoxicity; radicals; redox chemistry; selenophenes