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In Vitro Antifungal Activity Screening of Some New Glutamoyl derivatives

Author Affiliations

  • 1 Department of Chemistry, Kyambogo University, P.O. Box 1, Kyambogo, UGANDA

Res.J.chem.sci., Volume 4, Issue (8), Pages 17-24, August,18 (2014)


This research was focused at synthesizing new antifungal N-tosyl-L-glutamoyl derivatives with the aim of relating the structure with the expected biological activities. Synthesis N-tosyl-L-glutamic acid was prepared by reacting p-tosyl chloride with L-glutamic acid in sodium hydroxide-ether mixture. The anhydride was prepared by refluxing N-tosyl-L-glutamic acid with acetic anhydride. N-tosyl-L-glutamoy lamino acids were obtained using 1:1 mole of the tosyl derivatives with amino acids: glycine, L- alanine, L-Leucine , L-valine and L-tyrosine.N-tosyl-L-glutamoylamino acid methyl esters were prepared by the action of thionyl chloride in methanol on N-tosyl-L-glutamoylamino acid derivatives. N-tosyl-L-glutamoylaniline derivatives and N-tosyl-L-glutamoyl-p-amino benzoic acid were achieved by refluxing the amines and p-aminobenzoic acid in glacial acetic acid with the anhydride. The acid chloride was synthesized by refluxing N-tosyl-L-glutamoyl-p-amino benzoic acid in thionyl chloride. Stirring the acid chloride with appropriate amino acid in triethylamine-benzene mixture yielded the N-tosyl-L-glutamoyl-p-aminobenzoylamino acids. Esterifying these derivatives with Methanol in thionylchloride afforded the methyl esters. The acid azide was prepared by stirring sodium azide in dry benzene with N-tosyl-L-glutamoyl-p-aminobenzoyl chloride. N-tosyl-L-glutamoylamino phenyl ureaswere obtained by Curtius rearrangement by coupling of acid azides with appropriate amino acids in dry benzene. The structures of synthesized derivatives were confirmed by IR spectroscopy, H NMR spectroscopy at 90 MHz with TMS as internal standard and elemental analysis. The synthesized derivativeswere tested for their antifungal properties against five fungal isolates, Yeast, Fusariumsolani, Fusarium moniliforme, Penicillium expansum and cladosporiumcladosporioides. Twenty out of the 33 compounds of the N-Tosylglutamoyl derivatives had no activity on the tested micro-organisms, while 13 compounds were found to affect the growth of Yeast, Fusariumsolani, Fusarium moniliforme, Penicillium expansum and cladosporiumcladosporioides with varying degrees. The study showed that changing the structures of the synthesized compounds resulted in increased, decreased or a complete loss in biological activity, which proves that they could be of practical pharmaceutical application.


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