A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues

Özet

Some novel five-membered iminosugar analogues were efficiently synthesized via the MCRs of three components; amines, aldehydes and oxaloacetate to give 4-hydroxymethylpyrrolidines. Reduction of 3-hydroxy-4-carbomethoxy-3-pyrroliden-2-ones with Pd/C-catalyzed hydrogenation gave the corresponding cis-hydrogenated products at C3/C4stereoselectively. Then following reductions of ester and amide functionalities with LiAlH4afforded 4-(hydroxymethyl)pyrrolidin-3-ols. Among the synthesized compounds 4-hydrazineyl-3-hydroxymethyl-2-(4-methoxyphenyl)-N-methylpyrrolidine and 3-hydrazineyl-4-hydroxymethyl-1-methylpyrrolidine were found to be the most promising α-glucosidaseinhibitor with IC50values of 1.12and 1.17 mM, respectively.