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- W2084924570 abstract "The design, synthesis, and enzymic evaluation of cis- and trans-4-mercapto-6-oxo-1,4-azaphosphinane-2-carboxylic acid 4-oxide 5 against mammalian dihydroorotase is presented. The design strategy for 5 was based on the strong affinity of phosphinothioic acids for zinc and that 5 also resembles the postulated tetrahedral transition state for the enzyme-catalyzed reaction. The synthesis of 5 utilized a novel protection/deprotection sequence upon 4-hydroxy-6-oxo-1,4-azaphosphinane-2-carboxylic acid 4-oxide 4, followed by incorporation of α-phenyl benzenemethanethiol and exhaustive deprotection to afford 5 in 40% overall yield from 4. The activities of both isomers of 5 as inhibitors of mammalian dihydroorotase were marginally greater than that of the parent phosphinic acid 4, indicating a weak binding enhancement due to the phosphinothioic acid moiety." @default.
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- W2084924570 date "1998-10-17" @default.
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- W2084924570 title "Synthesis and Enzymic Evaluation of 4-Mercapto-6-oxo-1,4-azaphosphinane-2-carboxylic Acid 4-Oxide as an Inhibitor of Mammalian Dihydroorotase" @default.
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- W2084924570 doi "https://doi.org/10.1021/jm970814z" @default.
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