Synthesis and antimicrobial activity of some linear dipeptide pyridine and macrocyclic pentaazapyridine candidates

Abstract

Abstract A series of tetracarboxamide and macrocyclic tripeptides have been prepared starting from 3,5-bis[N-(1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)]pyridinecarboxamide 4 as starting material, which was synthesized from dinicotinic acid 1. Treatment of 4 with 1,4-diaminobutane, 1,6-diaminohexane, or cycloalkanone derivatives gave the corresponding macrocyclic tetracarboxamides (5a, b) and cycloalkyl hydrazone derivatives (6a–c), respectively. Additionally, the reaction of 4 with acetophenone or acetylpyridine derivatives gave the corresponding Schiff base derivatives 7a–e and 8a–c, respectively. Also, carboxylic acid hydrazide 4 was treated with acid anhydrides in glacial acetic acid to afford the corresponding diimide tetracarboxamide derivatives 9a, b, 10, and 11, respectively. The structures of newly synthesized compounds are established by physical and spectral data evidences. Some of the synthesized compounds were screened as antimicrobial agents.