ISSN 2326-7267
International Journal of Pharmacy and Pharmacology ISSN: 2326-7267 Vol. 9 (2), pp. 001-012, February, 2020. © International Scholars Journals
Full Length Research Paper
Synthesis and antimicrobial screening of peptidyl derivatives of bromocoumarins/methylimidazoles
Rajiv Dahiya1*, Rita Mourya1 and Subhash Chand Agrawal2
1Department of Pharmaceutical Chemistry, NRI Institute of Pharmacy, Bhopal, Madhya Pradesh, India.
2Department of Pharmaceutical Chemistry, Rajiv Academy for Pharmacy, Mathura, Uttar Pradesh, India.
Accepted 18 November, 2019
Abstract
In this investigation, it was of interest to synthesize novel series of peptide analogs of 3-bromocoumarins and 2-methylimidazoles. Substituted coumarinyl-oxyacetic acids 1, 2 were synthesized by alkylation of corresponding hydroxycoumarins with chloroacetic acid. The imidazolyl derivatives 13, 14 were prepared by interaction of 2-methylimidazole with substituted/unsubstituted anthranilic acids. Coupling of compounds 1, 2, 13 and 14 with different amino acid methyl ester hydrochlorides, dipeptide, tripeptide and tetrapeptide methyl esters afforded novel coumarino/imidazolopeptide derivatives 3-10 and 15-22. Selected peptide ester derivatives were further hydrolyzed by using lithium hydroxide to afford corresponding acid derivatives 11, 12 and 23, 24. The antibacterial and antifungal effects of synthesized peptide derivatives were studied against eight pathogenic microbes. Among the tested compounds, 19, 22 and its hydrolyzed analog 24 exhibited good antimicrobial activity against Pseudomonas aeruginosa, Klebsiella pneumoniae, Trichophyton mentagrophytes and Microsporum audouinii, and compounds 8, 10 and 12 displayed good antifungal activity against Candida albicans with minimum inhibitory concentration of 6.25 g/ml.
Key words: Bromocoumarin, methylimidazole, anthranilic acid, peptide coupling, antibacterial activity, antifungal activity.