Malken Bayrakdarian

Design, synthesis, and thrombin-inhibitory activity of pyridin-2-ones as P2/P3 core motifs.

Guided by available X-ray crystal structure data on the serine protease thrombin, a series of pyridin-2-one derivatives were designed and synthesized having diverse functionality at the P(1) and P(3) sites. Potent in vitro activity against thrombin, with excellent selectivity over trypsin was found for selected analogues.

Solution- and solid-phase asymmetric synthesis of substituted N-hydroxypyrrolidine dicarboxylic acids

Nitrone ylids prepared from α-amino aldehyde derivatives undergo 1,3-dipolar cyclocondensation reactions to give enantiopure C-4 branched N-hydroxy proline esters. The different functional groups can be manipulated to provide diversely substituted N-hydroxypyrrolidine dicarboxylic acids. The reaction can be adapted to solid-phase synthesis.

Pyrrolidine as a cogwheel-like scaffold for the deployment of diverse functionality through cycloaddition reactions of metallo-1,3-dipoles in aqueous media.

The reaction of glycinatocopper complexes with cinnamaldehydes under mildy basic aqueous conditions, affords polysubstituted prolines, which can be systematically modified in a number of chemoselective transformations.

Asymmetric synthesis of diversely substituted N-hydroxypyrrolidines using cycloadditions with chiral nitrone enolate/ylids

Abstract A stereoselective synthesis of diversely substituted N -hydroxypyrrolidines is reported, based on the cycloaddition reaction of chiral non-racemic nitrone ylids with a variety of α,β-unsaturated esters.