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

Molecules

Volumn 10, Issue 9, 2005, Pages 1218-1228

  Khattab, Sherine N ^a  

^a Alexandria University Faculty Of Science   (Egypt)

Author keywords

Amino acid hydrazide derivatives; Antimicrobial agents; Benzoic acid hydrazide; Copper and Cadmium complexes; Nicotinic acid hydrazide

Indexed keywords

AMINO ACID; ANTIINFECTIVE AGENT; DRUG DERIVATIVE; HYDRAZINE DERIVATIVE; NICOTINIC ACID; PROTON;

BACTERIUM; CHEMISTRY; CONFERENCE PAPER; DRUG EFFECT; MICROBIOLOGICAL EXAMINATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

AMINO ACIDS; ANTI-BACTERIAL AGENTS; BACTERIA; HYDRAZINES; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; NIACIN; PROTONS;

EID: 33644797503     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/10091218     Document Type: Conference Paper

References (19)

1. Barrett, D.; Tanaka, A.; Harada, K.; Ohki, H.; Watabe, E.; Maki, K.; Ikeda, F. Synthesis and biological activity of novel macrocyclic antifungals: acylated conjugates of the ornithine moiety of the lipopeptidolactone FR901469. Bioorg. Med. Chem. Lett. 2001, 11, 479-482.
2. Kovalainen, J. T.; Christians, J. A. M.; Kotisaari, S.; Laitinen, J. T.; Mannisto P.T. Synthesis and in vitro pharmacology of a series of new chiral histamine H3-receptor ligands:2-(R and S)-amino-3-(1H-imidazol-4(5)-yl)propyl ether derivatives. J.Med. Chem. 1999, 42, 1193-202.
3. El-Faham, A.; El Massry, A. M.; Amer, A.; Gohar, Y. M., A versatile synthetic route to chiral quinoxaline derivatives from amino acids precursors. Lett. Pept. Sci. 2002, 9, 49-54.
4. a) Polyak, F.; Lubell, W. D. Rigid dipeptide mimics: Synthesis of enantiopure 5- and 7-benzyl, and 5,7-dibenzyl indolizidinone amino acids via enolization and alkylation of δ-oxo α,ω-di-[N-(9-(9- phenylfluorenyl))amino]azelate esters. J. Org. Chem. 1998, 63, 5937-5949;
5. b) Roy, S.; Lombart, H.-G.; Lubell, W. D.; Hancock, R. E. W.; Farmer, S. W. Exploring relationships between mimic configuration, peptide conformation and biological activity in indolizidin-2-one amino acid analogs of gramicidin S. J. Peptide Res. 2002, 60, 198-214.
6. Okada, Y.; Tsukatani, M.; Taguchi, H.; Yokoi, T.; Bryant, S. D.; Lazarus, L. H. Amino acids and peptides. Design and synthesis of opioidmimetics containing pyrazinone ring and examination of their opioid receptor binding activity. Chem. Pharm. Bull. 1998, 46, 1374-82.
7. Sun, G.; Uretsky, N. J.; Wallace, L. J.; Shams, G.; Weinstein, D. M.; Miller, D. D. Synthesis of chiral l-(2'-amino-2'-carboxyethyl)-1,4-dihydro-6,7- quinoxaline-2,3-diones: α-amino-3-hydroxy-5-methyl-4-isoxazole propionate receptor agonists and antagonists. J. Med. Chem. 1996, 39, 4430-38.
8. Marsham, P. R.; Wardleworth, J. M.; Boyle, F. T., Hennequin, L. F.; Kimbell, R.; Brown, M.; Jackman, A. L. Design and synthesis of potent nonpolyglutamatable quinozoline antifolate thymidylate synthase inhibitors. Med. Chem., 1999, 42, 3809-20.
9. Xia, Y.; Yang, Z.-Y.; Xia, P.; Bastow, K. F.; Nakanishi, Y.; Lee, K.-H. Antitumor agents. Part 202: Novel 2'-amino chalcones: design, synthesis and biological evaluation. Bioorg. Med. Chem. Lett. 2000, 10, 699-701.
10. Kucukguzel, S. G.; Mazi, A.; Sahin, F.; Ozturk, S.; Stables J. Synthesis and biological activities of diflunisal hydrazide-hydrazones. Eur. J. Med. Chem. 2003, 38, 1005-1013.
11. Hassan, H. M.; Shedid, S. A. M. Synthesis and antimicrobial activity of some new Mannich bases, N-(2-hydroxy-1-naphthyl) amino acid, methyl ester and hydrazide derivatives. J. Serb. Chem. Soc. 1998, 63, 125-130.
12. Dogan, H. N.; Rollas, S.; Erdeniz, H., Synthesis, structure elucidation and antimicrobial activity of some 3-hydroxy-2-naphthoic acid hydrazide derivatives. Farmaco 1998, 53, 462-7.
13. Cesur, Z.; Büyüktimkin, S.; Büyüktimkin, N.; Derbentli, J. Synthesis and antimicrobial evaluation of some arylhydrazones of 4-[(2-methylimidazo[1,2-a]pyridine-3-yl)azo]benzoic acid hydrazine. Arch. Pharm. (Weinheim) 1990, 523, 141-4.
14. Cocco, M. T.; Congiu, C.; Onnis, V.; Pusceddu, M. C.; Schivo, M. L.; De Logu, A. Synthesis and antimycobacterial activity of some isonicotinoylhydrazones. Eur. J. Med. Chem. 1999, 34, 1071-6.
15. 2-2-imidazolinyl)-5,5'-dioxime and its mono- and tri-nuclear complexes. Trans. Met. Chem. 2000, 25, 421-25.
16. Chohan, Z. H.; Farooq, M. A.; Scozzafava, A.; Supuran, C. T. Antibacterial Schiff bases of oxalyl-hydrazine/diamide incorporating pyrrolyl and salicylyl moieties and their zinc(II) complexes. J. Enz. Inhib. Med. Chem. 2002, 17, 1-7.
17. Wu, G.; Wang, G.; Fu, X.; Zhu, L. Synthesis, crystal structure, stacking effect and antimicrobial studies of novel quaternary copper(II) complex with quinolone. Molecules, 2003, 8, 287-296.
18. rd ed; Dale M. M.; Foreman J. C.; Fan T-P. D. (eds), Blackwell Scientific Publications: London, 1994; pp. 16, 193.
19. Murray, P. R.; Baron, E. J.; Pfaller, M. A.; F. C. Tenover; Yolken, R. H. Manual of clinical microbiology. In: Antimicrobial Agents and Susceptibility Testing; Woods, G. L.; Washington J. A. (Eds.); American Society for Microbiology: Washington, DC, 1995.