Synthesis of chiral 3,5-bis(l-phenylalaninyl-l-leucinyl)pyridine Schiff base and their macrocyclic carboxaimide derivatives using 3,5-bis(l-phenylalaninyl)-pyridine methyl ester

Abstract

AbstractA series of linear tetrapeptides2–7and cyclooctapeptedopyridine derivatives8and9, were synthesized usingNα-dinicotinoyl-bis[(l-phenylalaninyl-l-leucyl)hydrazide]2as starting material. Acid hydrazide2was reacted with aromatic or heterocyclic aldehydes to give Schiff base derivatives3and4, respectively. Additionally, compound2was reacted with dicarboxylic acid anhydrides ortetracarboxylic diacid anhydrides to give the corresponding linear diimide carboxamides5–7, and octapeptide tetraimides8and9, respectively. The synthesized products were elucidated by using spectroscopic evidences and they were evaluated for their antibacterial activity by using streptomycin as reference antibiotic drug.