Cover Image

Synthesis, characterization and antibacterial activity of Methyl (2R)-2-benzamido-2-{[(1R)-2-methoxy-2-oxo- 1-phenylethyl]amino}acetate

Oumaima Karai, younas Aouine, Hassane Faraj, Alami Anouar, Mohammed Rachid Kabbour, Abdelilah El Hallaoui, Mohamed Bouksaim


The present work covers the recent synthetic of methyl (2R)-2-benzamido-2-{[(1R)-2-methoxy-2-oxo-1-phenylethyl]amino}acetate, via N-alkylation of methyl a-azido glycinate N-benzoylated with methyl 2-amino-2-phenylacetate in methylene chloride and in presence of triethylamine as basic catalyst. The structure of the prepared compound was determined by spectroscopic methods: 1H-NMR, 13C-NMR, MS data, elemental analysis and confirmed by X-Ray diffraction. This compound was screened in vitro for its antibacterial activity against Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa and Salmonella enteric). The MIC values confirmed that the title compound had a bactericidal effect against the strains tested.

Full Text:



- V.S. Vinutha, N. Badiadka, K.S. Balladka, N-(4-Nitrophenyl)-2-{2-[3-(4-chlorophenyl)-5-[4-(propan-2- yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl]-4-oxo-4,5-dihydro-1,3-thiazol-5-yl}acetamide. Molbank 2017, M943. DOI: 10.3390/M943.

- L.C. Chou, L.J. Huang, J.S. Yang, F.Y.Lee, C.M.Teng, S.C. Kuo, Synthesis of furopyrazole analogs of 1-benzyl-3-(5-hydroxymethyl-2-furyl)indazole (YC-1) as novel anti-leukaemia agents. Bioorg. Med. Chem. 2007, 15, 1732-1740. PMID: 17189698.

- J. Li, Y.F. Zhao, X.L. Zhao, X.Y. Yuan, P. Gong, Synthesis and anticancer activities of novel 1,4-disubstituted phthalazines. Molecules 2006, 11, 574-582. PMID: 17971729.

- A.A. Elhenawy, Design, synthesis of new amino acid derivatives and evaluate DNA binding activity, anticancer and antimicrobial activity. Int. J. of Bioorg. Chem. 2017, 2, 36-50. DOI: 10.11648/j.ijbc.20170202.11.

- R.Z. Yan, X.Y. Liu, W.F. Xu, C. Pannecouque, M. Witvrouw, E. De Clercq, Synthesis and anti-HIV evaluation of the novel 2-(m-chlorobenzyl)-4-substituted-7-methyl-1,1,3-trioxo-pyrazolo[4,5-e] [1,2,4]thiadiazines. Arch. Pharm. Res. 2006, 29, 957-962. PMID: 17146963.

- R. Subinoy, B. Avinash, M. Rubul, M.R. Vincent, Monolayer coated gold nanoparticles for delivery applications. Advanced Drug Delivery Reviews 2012, 64, 200-216.

- E.H. Mabrouk, A. Elachqar, A. Alami, A. El Hallaoui, Synthesis of new racemic α,αdiaminocarboxylic ester derivatives. Molecules 2010, 13, 9354-9363. DOI: 10.3390/molecules15129354.

- O. Karai, M. El Hamdani, H. Faraj, A. Alami, M.R. Kabbour, A. El Hallaoui, M. Bouksaim, Y. Aouine, Methyl N-[1-(benzoylamino)-2-methoxy-2-oxoethyl]-tryptophanate. Molbank 2017, M958; DOI:10.3390/M958.

- W. Steglich, R. Kober, Untersuchungen zur Reaktion von Acylaminobrommalonestern und Acylaminobromessigestern mit Trialkylphosphiten-eine einfache Synthese von 2-Amino-2-(diethoxyphosphoryl)Essigsäure Ethylester. Liebigs Ann Chem. 1983, 4, 599-609.

- S. Achamlale, A. Elachqar, A. El Hallaoui, S. El Hajji, M.L. Roumestant, Ph. Viallefont, Synthesis of α- triazolyl α-amino acid derivatives. Amino Acids 1997, 12, 257-263.

- S. Achamlale, A. Elachqar, A. El Hallaoui, S. El Hajji, A. Alami, M.L. Roumestant, Ph. Viallefont, Synthesis of biheterocyclic

α-amino acid. Amino Acids 1999, 17, 149-163.

- O. Karai, Y. Aouine, H. Faraj, A. Alami, A. El Hallaoui, H. Zouihri, Methyl (2R)-2-benzamido-2-{[(1R)-2-methoxy-2-oxo-1-phenylethyl]amino}acetate. IUCr Data 2017, 2, x171155.



  • There are currently no refbacks.

Copyright (c) 2018 Mediterranean Journal of Chemistry