title: Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation.
abstract: In the chalcone scaffold, it is thought that the double bond is an important structural linker but it is likely not essential for the interaction with tubulin. Yet, it may be a potential site of metabolic degradation and interaction with biological nucleophiles. In this letter, we have replaced this olefinic portion of chalcones with two metabolically stable and chemically inert heterocyclic rings, namely triazole or tetrazole. Yet, our biologic data suggest that, unlike in other antitubulinic structures, the olephinic ring might not be merely a structural linker.
authors.affiliation: Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche and Drug and Food Biotechnology Center, Università degli Studi del Piemonte Orientale A. Avogadro, Via Bovio 6, 28100 Novara, Italy.
authors.forename: Ornella
authors.initials: O
authors.lastname: Mesenzani
authors.forename: Alberto
authors.initials: A
authors.lastname: Massarotti
authors.forename: Mariateresa
authors.initials: M
authors.lastname: Giustiniano
authors.forename: Tracey
authors.initials: T
authors.lastname: Pirali
authors.forename: Valentina
authors.initials: V
authors.lastname: Bevilacqua
authors.forename: Antonio
authors.initials: A
authors.lastname: Caldarelli
authors.forename: Pierluigi
authors.initials: P
authors.lastname: Canonico
authors.forename: Giovanni
authors.initials: G
authors.lastname: Sorba
authors.forename: Ettore
authors.initials: E
authors.lastname: Novellino
authors.forename: Armando A
authors.initials: AA
authors.lastname: Genazzani
authors.forename: Gian Cesare
authors.initials: GC
authors.lastname: Tron
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D047188:Chalcones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D008958:Models, Molecular; D009447:Neuroblastoma / Q000188:drug therapy; D013777:Tetrazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014404:Tubulin / Q000378:metabolism; D050257:Tubulin Modulators / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D047188:Chalcones; D013777:Tetrazoles; D014230:Triazoles; D014404:Tubulin; D050257:Tubulin Modulators