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  • Title: Synthesis of novel inhibitors of the HIV-1 protease: difunctional enols of simple N-protected amino acids.
    Author: Vaillancourt M, Vanasse B, Le Berre N, Cohen E, Sauvé G.
    Journal: Bioorg Med Chem; 1994 May; 2(5):343-55. PubMed ID: 7922146.
    Abstract:
    A series of enol HIV-1 protease inhibitors which show competitive inhibition and the structure-activity relationship study which led to the design of these compounds are reported. By systematically modifying simple amino acids, Boc-Phe enol and Boc-Tyr enol derivatives yield nanomolar Kiapp values (Kiapp = 0.485 microM and Kiapp = 0.425 microM, respectively). These enols are of low molecular weight (< 500 g/mol) and of non-peptidic nature. The enols are synthesized in a one step chemical synthesis and modifications to increase their potency could easily be performed. Boc-Phe enol and Boc-Tyr enol showed low inhibitory effect on pepsin, Kiapps of 23 and 149 microM, respectively, and Boc-Phe enol showed a Kiapp of 20 microM for cathepsin D. Neither of these two compounds inhibited renin (< 10% inhibition at 200 microM).
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