Synthesis and biological activity of novel amino acid-(N′-benzoyl) hydrazide and amino acid-(N′-nicotinoyl) hydrazide derivatives.

The coupling reaction of benzoic acid and nicotinic acid hydrazides with N-protected L-amino acids including valine, leucine, phenylalanine, glutamic acid and tyrosine is reported. The target compounds, N-Boc-amino acid-(N'-benzoyl)- and N-Boc-amino acid-(N'-nicotinoyl) hydrazides 5a-5e and 6a-6e were prepared in very high yields and purity using N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methyl-methanaminium hexafluorophosphate N-oxide (HATU) as coupling reagent. The antimicrobial activity of the Cu and Cd complexes of the designed compounds was tested. The products were deprotected affording the corresponding amino acid-(N'-benzoyl) hydrazide hydrochloride salts (7a-7e) and amino acid-(N'-nicotinoyl) hydrazide hydrochloride salts (8a-8e). These compounds and their Cu and Cd complexes were also tested for their antimicrobial activity. Several compounds showed comparable activity to that of ampicillin against S. aureus and E. coli.