title: Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease.
abstract: A versatile synthesis of hydroxylated and epoxy 1-azepin 2-ones substituted at N1, C-3 and C-4 or C-7 has been developed. The sequence involves ring-closing metathesis of an amino acid derived diene amide, followed by either epoxidation or dihydroxylation, of the resulting alkene. Assay of the product epoxides (10, 18, 25) and diols (9a, 17, 24) against HIV protease reveals micromolar inhibition.
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand.
authors.forename: Shazia
authors.initials: S
authors.lastname: Zaman
authors.forename: Pietro
authors.initials: P
authors.lastname: Campaner
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Abell
mesh_terms: D016333:HIV Protease / Q000378:metabolism*; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D017320:HIV Protease Inhibitors; D007769:Lactams; D016333:HIV Protease