Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease.
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.
Zaman
Shazia
S
Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand.
Campaner
Pietro
P
Abell
Andrew D
AD
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
D017320:HIV Protease Inhibitors; D007769:Lactams; D016333:HIV Protease