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- W2023281210 abstract "Dipeptide analogues incorporating allophenylnorstatine [Apns; (2S, 3S)-3amino-2-hydroxy-4-phenylbutyric acid] as a transition state mimic at the scissile bond were designed and synthesized in the hope of obtaining a novel KNI series of HIV protease inhibitors. The precursors, N-P2′-3-(2S, 3S)-3-(tert-butyloxy-carbonyl)amino-2-hydroxy-4-phenylbutanoyl)-5, 5-dimethylthiazolidine-4-carboxamide (N-Boc-Apns-Dmt-P2′) 4a–p were prepared by deprotection of the synthones N-P2′-(tert-butyloxycarbonyl)-5, 5-dimethylthiazolidine-4-carboxamide (Boc-Dmt-P2′) 2a–p, then coupling with (2S, 3S)3-(tert-butyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoic acid (N-Boc-Apns-OH) 3. The deprotected intermediates 4 were coupled with the activated carboxyl groups of the P2 ligands to afford the target dipeptides. In this work, we fixed at the P2 site either a 2, 6-dimethylphenoxyacetyl or a 3-hydroxy-2-methylbenzoyl group. Substitutes at the P2′ site were varied to afford the members of the series 7 and 8. Improved activity of most of the members of series 8 relative to their analogues of series 7 can be partially attributed to the differences in the structures of the P2 moieties. Positional isomerism in the P2′ moieties significantly affected the activity and polarity of the target." @default.
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- W2023281210 date "2004-11-01" @default.
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- W2023281210 title "A Novel Dipeptide-based HIV Protease Inhibitor Containing Allophenylnorstatine" @default.
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- W2023281210 doi "https://doi.org/10.1002/ardp.200400882" @default.
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