Synthesis of cis-4-guanidino-l-proline and 1-carbamimidoyl-l-proline derivatives as influenza neuraminidase inhibitors

Abstract

Simple methods for synthesizing cis-4-guanidino-L-proline derivatives and 1-carbamimidoyl-L-proline derivatives as influenza neuraminidase inhibitors were developed. All of these compounds were prepared originally from L-hydroxyproline through a key intermediate. Among them, compound 4d with the scaffold of cis-4-guanidino-L-proline was the best inhibitor. The docking studies indicated that it could interact with the active site of NA similar to the binding pattern of peramivir. These compounds and the synthetic methods could be useful for exploration of novel influenza NA inhibitors.

MgI2‐chemoselective cleavage for removal of amino acid protecting groups: A fresh vision for peptide synthesis

“…The Boc group could also be removed from Boc‐Trp(For)‐OH, without affecting the N ‐in formyl moiety (Table , entry 13). It is well known that a t ‐butyl ester or a Boc N ‐protecting group, are more sensitive to acidic conditions than a N ‐benzoyl or a N ‐formyl group . The same occurred in the MgI 2 ‐MW mediated cleavage.…”