tetano
Editor, Senior Moderator
Org Biomol Chem. 2017 Mar 24. doi: 10.1039/c7ob00331e. [Epub ahead of print]
[h=1]Stereoselective synthesis of novel adamantane derivatives with high potency against rimantadine-resistant influenza A virus strains.[/h] Kuznetsov NY[SUP]1[/SUP], Tikhov RM[SUP]1[/SUP], Godovikov IA[SUP]1[/SUP], Medvedev MG[SUP]1[/SUP], Lyssenko KA[SUP]1[/SUP], Burtseva EI[SUP]2[/SUP], Kirillova ES[SUP]2[/SUP], Bubnov YN[SUP]3[/SUP].
[h=3]Author information[/h]
[h=3]Abstract[/h] A series of (R)- and (S)-isomers of new adamantane-substituted heterocycles (1,3-oxazinan-2-one, piperidine-2,4-dione, piperidine-2-one and piperidine) with potent activity against rimantadine-resistant strains of influenza A virus were synthesized through the transformation of adamantyl-substituted N-Boc-homoallylamines 8 into piperidine-2,4-diones 11 through the cyclic bromourethanes 9 and key intermediate enol esters 10. Biological assays of the prepared compounds were performed on the rimantadine-resistant S31N mutated strains of influenza A - A/California/7/2009(H1N1)pdm09 and modern pandemic strain A/IIV-Orenburg/29-L/2016(H1N1)pdm09. The most potent compounds were both enantiomers of the enol ester 10 displaying IC[SUB]50[/SUB] = 7.7 μM with the 2016 Orenburg strain.
PMID: 28338150 DOI: 10.1039/c7ob00331e
[h=1]Stereoselective synthesis of novel adamantane derivatives with high potency against rimantadine-resistant influenza A virus strains.[/h] Kuznetsov NY[SUP]1[/SUP], Tikhov RM[SUP]1[/SUP], Godovikov IA[SUP]1[/SUP], Medvedev MG[SUP]1[/SUP], Lyssenko KA[SUP]1[/SUP], Burtseva EI[SUP]2[/SUP], Kirillova ES[SUP]2[/SUP], Bubnov YN[SUP]3[/SUP].
[h=3]Author information[/h]
[h=3]Abstract[/h] A series of (R)- and (S)-isomers of new adamantane-substituted heterocycles (1,3-oxazinan-2-one, piperidine-2,4-dione, piperidine-2-one and piperidine) with potent activity against rimantadine-resistant strains of influenza A virus were synthesized through the transformation of adamantyl-substituted N-Boc-homoallylamines 8 into piperidine-2,4-diones 11 through the cyclic bromourethanes 9 and key intermediate enol esters 10. Biological assays of the prepared compounds were performed on the rimantadine-resistant S31N mutated strains of influenza A - A/California/7/2009(H1N1)pdm09 and modern pandemic strain A/IIV-Orenburg/29-L/2016(H1N1)pdm09. The most potent compounds were both enantiomers of the enol ester 10 displaying IC[SUB]50[/SUB] = 7.7 μM with the 2016 Orenburg strain.
PMID: 28338150 DOI: 10.1039/c7ob00331e