Molecules 2008, 13(4), 958-976; doi:10.3390/molecules13040958
Article

Synthesis and Biological Activity of Peptide Derivatives of Iodoquinazolinones/Nitroimidazoles

Department of Pharmaceutical Chemistry, Rajiv Academy for Pharmacy, Mathura-281001 (UP), India
* Author to whom correspondence should be addressed.
Received: 3 April 2008; in revised form: 18 April 2008 / Accepted: 19 April 2008 / Published: 24 April 2008
PDF Full-text Download PDF Full-Text [268 KB, uploaded 1 October 2008 09:18 CEST]
Abstract: Two substituted quinazolinyl/imidazolyl-salicylic acids 5, 6 were synthesized bythe reaction of 6-iodo-2-methylbenzoxazin-4-one/5-nitroimidazole with 5-aminosalicylicacid (5-ASA). Coupling of compounds 5 and 6 with different amino acid esterhydrochlorides, dipeptide and tripeptide methyl esters yielded novelquinazolino/imidazolopeptide derivatives 5a-f and 6a-g. The chemical structures of allnewly synthesized compounds were confirmed by means of FT-IR, 1H- and 13C-NMR, MSand elemental analysis. Selected peptide ester derivatives were further hydrolyzed by usinglithium hydroxide (LiOH) to afford the corresponding acid derivatives 5ba-da and 6ea-ga.All peptide derivatives were assayed for antimicrobial and anthelmintic activities againsteight pathogenic microbes and three earthworm species. Among the tested compounds, 5e,5d, 6e and their hydrolyzed analogs 5da and 6ea exhibited higher antimicrobial activityagainst Pseudomonas aeruginosa, Klebsiella pneumoniae and Candida albicans, and 5a,6g and 6ga displayed better antifungal activity against the dermatophytes Trichophytonmentagrophytes and Microsporum audouinii. Moreover, 6f and its hydrolyzed derivative6fa showed good anthelmintic activity against Megascoplex konkanensis, Pontoscotexcorethruses and Eudrilus eugeniea at dose of 2 mg mL–1.
Keywords: Quinazolinone; imidazole; 5-aminosalicylic acid; peptides; antimicrobial activity; anthelmintic activity.

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

MDPI and ACS Style

Dahiya, R.; Kumar, A.; Yadav, R. Synthesis and Biological Activity of Peptide Derivatives of Iodoquinazolinones/Nitroimidazoles. Molecules 2008, 13, 958-976.

AMA Style

Dahiya R, Kumar A, Yadav R. Synthesis and Biological Activity of Peptide Derivatives of Iodoquinazolinones/Nitroimidazoles. Molecules. 2008; 13(4):958-976.

Chicago/Turabian Style

Dahiya, Rajiv; Kumar, Anil; Yadav, Rakesh. 2008. "Synthesis and Biological Activity of Peptide Derivatives of Iodoquinazolinones/Nitroimidazoles." Molecules 13, no. 4: 958-976.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert