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We have developed concise and efficient syntheses of novel spirocyclic pyrrolidones 1-3, which involve the alkylation of pyrrolidone precursor 13 with 1,5-dibromopentane, 16 and 15, followed by an in situ lactamization. Conjugates of 1 and 2 with P1'/P2' hydroxy-indanolamine moiety resulted in novel and potent inhibitors of HIV-1 protease 25 and 26, suggesting that 1 and 2 are novel P2/P1 HIV-PI mimetics.


Wieslaw M Kazmierski, Eric Furfine, Andrew Spaltenstein, Lois L Wright. Novel spirocyclic pyrrolidones as P2/P1 mimetics in potent inhibitors of HIV-1 protease. Bioorganic & medicinal chemistry letters. 2002 Dec 2;12(23):3431-3

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PMID: 12419377

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