title: Design, synthesis, and evaluation of analogues of (+)-14-normethyldiscodermolide.
abstract: [Structure: see text] The design, syntheses, and biological evaluation of nine totally synthetic analogues of the microtubule-stabilizing agent (+)-14-normethyldiscodermolide (2) are reported. Simplification at the C(21)-C(24) terminal diene and at the C(1)-C(5) lactone moieties reveals significant structure-activity relationships.
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
authors.forename: Amos B
authors.initials: AB
authors.lastname: Smith
authors.forename: B Scott
authors.initials: BS
authors.lastname: Freeze
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Lamarche
authors.forename: Tomoyasu
authors.initials: T
authors.lastname: Hirose
authors.forename: Ignacio
authors.initials: I
authors.lastname: Brouard
authors.forename: Ming
authors.initials: M
authors.lastname: Xian
authors.forename: Kurt F
authors.initials: KF
authors.lastname: Sundermann
authors.forename: Simon J
authors.initials: SJ
authors.lastname: Shaw
authors.forename: Mark A
authors.initials: MA
authors.lastname: Burlingame
authors.forename: Susan Band
authors.initials: SB
authors.lastname: Horwitz
authors.forename: David C
authors.initials: DC
authors.lastname: Myles
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: C511441:14-normethyldiscodermolide; D000475:Alkenes; D000970:Antineoplastic Agents; D002219:Carbamates; D007783:Lactones; D011753:Pyrones