title: Versatile routes to marine sponge metabolites through benzylidene rhodanines.
abstract: The first total synthesis of the marine natural products Psammaplin C and Tokaradine A is described. Benzylidene rhodanines were utilized as versatile intermediates toward the synthesis of seven brominated marine sponge metabolites through the optimization of protection group strategies. Spermatinamine demonstrated good inhibition of all cancer cell lines tested, in particular the leukemia K562 and colon cancer HT29 cell lines.
authors.affiliation: Sunderland Pharmacy School, Department of Pharmacy, Health & Well Being, University of Sunderland, Wharncliffe Street, Sunderland, SR1 3SD, UK.
authors.forename: Suresh K
authors.initials: SK
authors.lastname: Kottakota
authors.forename: Mathew
authors.initials: M
authors.lastname: Benton
authors.forename: Dimitrios
authors.initials: D
authors.lastname: Evangelopoulos
authors.forename: Juan D
authors.initials: JD
authors.lastname: Guzman
authors.forename: Sanjib
authors.initials: S
authors.lastname: Bhakta
authors.forename: Timothy D
authors.initials: TD
authors.lastname: McHugh
authors.forename: Mark
authors.initials: M
authors.lastname: Gray
authors.forename: Paul W
authors.initials: PW
authors.lastname: Groundwater
authors.forename: Emma C L
authors.initials: EC
authors.lastname: Marrs
authors.forename: John D
authors.initials: JD
authors.lastname: Perry
authors.forename: J Jonathan
authors.initials: JJ
authors.lastname: Harburn
mesh_terms: D000818:Animals; D001597:Benzylidene Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D019073:HT29 Cells; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D012236:Rhodanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013096:Spermine / Q000031:analogs & derivatives / Q000494:pharmacology; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014443:Tyrosine / Q000031:analogs & derivatives / Q000494:pharmacology
chemical_list: D001597:Benzylidene Compounds; D006842:Hydrocarbons, Brominated; D013450:Sulfones; C578914:psammaplin C; C525803:spermatinamine; C578913:tokaradine A; D013096:Spermine; D014443:Tyrosine; D012236:Rhodanine