Synthesis and Biological Activity of Peptide Derivatives of Iodoquinazolinones/Nitroimidazoles

Molecules

Rajiv Dahiya¹  Anil Kumar² 

[1] id="af1-molecules-13-00958">Department of Pharmaceutical Chemistry, Rajiv Academy for Pharmacy, Mathura-281001 (UP), Ind

关键词: Quinazolinone;    imidazole;    5-aminosalicylic acid;    peptides;    antimicrobial activity;    anthelmintic activity.;   

DOI  :  10.3390/molecules13040958

来源: mdpi

【 摘 要 】

Two substituted quinazolinyl/imidazolyl-salicylic acids 5, 6 were synthesized by the reaction of 6-iodo-2-methylbenzoxazin-4-one/5-nitroimidazole with 5-aminosalicylic acid (5-ASA). Coupling of compounds 5 and 6 with different amino acid ester hydrochlorides, dipeptide and tripeptide methyl esters yielded novel quinazolino/imidazolopeptide derivatives 5a-f and 6a-g. The chemical structures of all newly synthesized compounds were confirmed by means of FT-IR, ¹H- and ¹³C-NMR, MS and elemental analysis. Selected peptide ester derivatives were further hydrolyzed by using lithium hydroxide (LiOH) to afford the corresponding acid derivatives 5b_a-d_a and 6e_a-g_a. All peptide derivatives were assayed for antimicrobial and anthelmintic activities against eight pathogenic microbes and three earthworm species. Among the tested compounds, 5e, 5d, 6e and their hydrolyzed analogs 5d_a and 6e_a exhibited higher antimicrobial activity against Pseudomonas aeruginosa, Klebsiella pneumoniae and Candida albicans, and 5a, 6g and 6g_a displayed better antifungal activity against the dermatophytes Trichophyton mentagrophytes and Microsporum audouinii. Moreover, 6f and its hydrolyzed derivative 6f_a showed good anthelmintic activity against Megascoplex konkanensis, Pontoscotex corethruses and Eudrilus eugeniea at dose of 2 mg mL^–1.

【 授权许可】

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