Synthesis, Characterization and Antibacterial Activity of Methyl N-[1-(benzoylamino)-2-methoxy-2-oxoethyl]Tryptophanate

Oumaima Karai; Younas Aouine; Anouar Alami; Hassane Faraj; Abdelilah El Hallaoui

Oumaima Karai Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.
Younas Aouine Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco and Department of Chemistry, Faculty of Sciences, Ibn Zohr University, P.B. 8106, Cit� Dakhla, Agadir 80060, Morocco.
Anouar Alami Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.
Hassane Faraj Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.
Abdelilah El Hallaoui Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.

Keywords: Antibacterial activity, carboxylic amino esters, N-alkylation

Abstract

The title compound, methyl N-[1-(benzoylamino)-2-methoxy-2-oxoethyl]tryptophanate 2, have been synthesized in high yield, via N-alkylation reaction of methyl 2-azido-2-benzamidoacetate with methyl 2-amino-3-(1H-indol-3-yl)propanoate in acetone, with the presence of diisopropylethylamine as a base. The structure of the prepared compound was characterized by ¹H, ¹³C NMR in addition to MS, X-Ray diffraction data, and elemental analysis. This compound was tested 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 showed that the synthesized compound had a bactericidal effect against the strains tested.