Conformationally constrained analogues of diacylglycerol having a perhydrofuro[3,4-c]furan-1,4-dione bis-γ-butyrolactone skeleton

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Abstract

Bis-γ-lactones (1, 2) having a perhydrofuro[3,4-c]furan-1,4-dione skeleton were designed as conformationally constrained diacylglycerol analogues. They were synthesized from D-apiose in 11 steps, and evaluated as PKC-α ligands by measuring their ability to displace bound [3H]-PDBU from the enzyme. The compounds showed moderate binding affinities with Ki values of 13.89 (±5.67) μM and 11.47 (±0.89) μM, respectively. Their similar binding affinities indicate that these two bicyclic compounds were not effectively discriminated by PKC-α in terms of the direction of the side chain as other ligands built on similar bis-γ-lactones.

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