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  • Title: High-speed synthesis of potent C2-symmetric HIV-1 protease inhibitors by in-situ aminocarbonylations.
    Author: Wannberg J, Kaiser NF, Vrang L, Samuelsson B, Larhed M, Hallberg A.
    Journal: J Comb Chem; 2005; 7(4):611-7. PubMed ID: 16004505.
    Abstract:
    Two novel series of C2-symmetric HIV-1 protease inhibitors were synthesized by microwave-promoted, palladium-catalyzed aminocarbonylations of the o-iodo- and m-bromobenzyloxy P1/P1' substituted core structures. Molybdenum hexacarbonyl was used as a convenient solid source of carbon monoxide in these transformations. After the initial high-speed library generation, biological testing identified highly active HIV-1 protease inhibitors. Selected ortho- and meta-decorated inhibitors were subsequently resynthesized on a larger scale and retested for their affinity toward HIV-1 protease, showing micromolar to low nanomolar inhibition. The discovery of highly active inhibitors containing large phenyl amide ortho substituents in the P1/P1' positions indicates that larger groups than previously believed are tolerated in this part of the S1/S1' pocket.
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