title: Design and total synthesis of a fluorescent phorboxazole A analog for cellular studies.
abstract: To enable studies to elucidate the intracellular processing and targeting of the potent cytostatic/apoptotic anticancer natural products phorboxazoles A and B, a fluorescent derivative has been developed. This involved the total syntheses of the terminal alkyne 33-O-Me-45,46-dehydrobromophorboxazole A (MDHBPA) and a terminal vinyl iodide derivative of the blue fluorescent dye N,N,-dimethyl-7-aminocoumarin (DMC). Sonogashira coupling of these partners provided enyne DMC-MDHBPA in high yield.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.
authors.forename: Jiehao
authors.initials: J
authors.lastname: Chen
authors.forename: Lu
authors.initials: L
authors.lastname: Ying
authors.forename: T Matthew
authors.initials: TM
authors.lastname: Hansen
authors.forename: Mary M
authors.initials: MM
authors.lastname: Engler
authors.forename: Chi Sing
authors.initials: CS
authors.lastname: Lee
authors.forename: James J
authors.initials: JJ
authors.lastname: La Clair
authors.forename: Craig J
authors.initials: CJ
authors.lastname: Forsyth
mesh_terms: D049933:Aminocoumarins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D008968:Molecular Conformation; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D049933:Aminocoumarins; D000970:Antineoplastic Agents; D005456:Fluorescent Dyes; D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; C408887:phorboxazole A