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Tropical Journal of Pharmaceutical Research
Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, Nigeria
ISSN: 1596-5996
EISSN: 1596-9827
Vol. 15, No. 2, 2016, pp. 393-404
Bioline Code: pr16052
Full paper language: English
Document type: Research Article
Document available free of charge

Tropical Journal of Pharmaceutical Research, Vol. 15, No. 2, 2016, pp. 393-404

 en Synthesis and Evaluation of Antimicrobial Activity of Some 2-Morpholinomethylamino-4-(7-Unsubstituted/Substituted Coumarin-3-yl)-6-Chlorosubstitutedphenyl Pyrimidines
Imran, Mohd; Alsalman, Abida & Alsalman, Abdulkhaliq J.

Abstract

Purpose: To prepare some 2-morpholinomethylamino-4-(7-unsubstituted/substitutedcoumarin-3-yl)-6- chlorosubstitutedphenyl pyrimidines as antimicrobial agents.
Methods: Some 2-morpholinomethylamino-4-(7-unsubstituted/substitutedcoumarin-3-yl)-6-chlorosubstitutedphenyl pyrimidines were prepared by reacting 2-amino-4-(7-substituted/unsubstituted coumarin-3-yl)-6-(chlorosubstitutedphenyl) pyrimidines with morpholine and formaldehyde. The chemical structures of the synthesized compounds were elucidated by their Fourier Transform infra-red (FTIR), 1H-nuclear magnetic resonance (1H-NMR) and mass spectra, as well as by elemental analysis. These compounds were investigated for their antimicrobial activity against ten bacteria and five fungi by serial plate dilution method using the standard drugs, ofloxacin and ketoconazole, respectively, and their minimum inhibitory concentrations (MICs) were determined.
Results: A total of eighteen new compounds (1a-18a) were synthesized. Compound 3a (MIC = 75 μg/mL; p < 0.0001) and 15a (MIC = 125 μg/mL; p < 0.001) produced stronger antifungal activity than the standard drug, ketoconazole (MIC = 25 μg/mL; p < 0.0001) against P. citrinum check for this species in other resources . Compound 4a displayed higher but moderate activity against Gram-positive bacterium, S. aureus check for this species in other resources (MIC = 100 μg/mL; p < 0.05) than the standard drug, ofloxacin (MIC = 25 μg/mL; p < 0.0001). Compound 4a also displayed higher but moderate activity against the Gram-negative bacterium, E. coli check for this species in other resources (MIC = 75 μg/mL; p < 0.0001) than the standard drug, ofloxacin (MIC = 12.5 μg/mL; p < 0.0001). The structure activity relationship analysis revealed that the chloro- substitution at position 2 of the phenyl ring along with a chlorobromosubstituted coumarin moiety of the synthesized compounds is critical for activity against Gram-positive bacteria, Gram negative bacteria and fungi.
Conclusion: The synthesized compounds are relatively active antifungal agents but are weak antibacterial agents. However, they require further evaluation of their antifungal activity against other fungal strains to ascertain their broad spectrum activity.

Keywords
Pyrimidine; Coumarin; Morpholine; Antibacterial; Antifungal; Structure-activity relationship

 
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