title: Synthesis and biological properties of the cytotoxic 14-membered macrolides aspergillide A and B.
abstract: Total, stereoselective syntheses of the naturally occurring, cytotoxic macrolides aspergillide A and B are described. Olefin metatheses and asymmetric allylations were key steps in the synthetic sequences. Cytotoxicity assays against several tumor cell lines have been performed for the two aspergillides and some of the intermediates or side products of the synthetic sequence. One of these intermediates has been found markedly active against the human leukemia cancer cell line HL-60, with an IC(50) value comparable with that of the clinical drug fludarabine.
authors.affiliation: Depart. de Q. Inorgánica y Orgánica, Univ. Jaume I, Avda. Sos Baynat s/n, 12071 Castellón, Spain.
authors.forename: Santiago
authors.initials: S
authors.lastname: Díaz-Oltra
authors.forename: César A
authors.initials: CA
authors.lastname: Angulo-Pachón
authors.forename: Juan
authors.initials: J
authors.lastname: Murga
authors.forename: Eva
authors.initials: E
authors.lastname: Falomir
authors.forename: Miguel
authors.initials: M
authors.lastname: Carda
authors.forename: J Alberto
authors.initials: JA
authors.lastname: Marco
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001230:Aspergillus / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008386:Marine Biology; D015394:Molecular Structure; D013237:Stereoisomerism; D014740:Vidarabine / Q000031:analogs & derivatives / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D018942:Macrolides; C526623:aspergillide A; D014740:Vidarabine; C024352:fludarabine