title: Enantioselective total syntheses of the proposed structures of prevezol B and evaluation of anti-cancer activity.
abstract: The first enantioselective total syntheses of the proposed structures of the natural product prevezol B are reported. The reported syntheses complement the previously-reported syntheses of the proposed structures of prevezol C, a stereoisomer of prevezol B. It was previously shown that the structure of the naturally occurring prevezol C had been incorrectly assigned. This work has led us to conclude that the proposed structures of prevezol B are also incorrect and major revision of both of the structures of the prevezols B and C is required. Cytotoxicity studies on the human cervical cancer cell line HeLa revealed that the synthesized prevezol B and C compounds were not active even at the highest concentration used (100 μM). However, one of the synthetic precursors was shown to have modest potency against HeLa cells (IC50 = 23.5 ± 1.8 μM).
authors.affiliation: School of Chemistry, Monash University, Clayton, Victoria 3800, Australia. Kellie.Tuck@monash.edu.
authors.forename: Anna E
authors.initials: AE
authors.lastname: Leung
authors.forename: Riccardo
authors.initials: R
authors.lastname: Rubbiani
authors.forename: Gilles
authors.initials: G
authors.lastname: Gasser
authors.forename: Kellie L
authors.initials: KL
authors.lastname: Tuck
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D049109:Cell Proliferation / Q000187:drug effects; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001688:Biological Products; D004224:Diterpenes; C583648:prevezol C