Synthesis and Biological Activity of Novel Amino Acid-(N'-Benzoyl) Hydrazide and Amino Acid-(N'-Nicotinoyl) Hydrazide Derivatives
Sherine N. Khattab Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt
Molecules 2005, 10(9), 1218-1228; https://doi.org/10.3390/10091218
Received: 9 November 2004 / Revised: 12 July 2005 / Accepted: 13 July 2005 / Published: 30 September 2005
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-yl- methylene]-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.
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Keywords:
Benzoic acid hydrazide; nicotinic acid hydrazide; amino acid hydrazide derivatives; Copper and Cadmium complexes; antimicrobial agents.
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MDPI and ACS Style
Khattab, S.N. Synthesis and Biological Activity of Novel Amino Acid-(N'-Benzoyl) Hydrazide and Amino Acid-(N'-Nicotinoyl) Hydrazide Derivatives. Molecules 2005, 10, 1218-1228.
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