Next Article in Journal
Microwave-Enhanced Sulphated Zirconia and SZ/MCM-41 Catalyzed Regioselective Synthesis of β-Amino Alcohols Under Solvent-Free Conditions
Previous Article in Journal
CuO and Ag2O/CuO Catalyzed Oxidation of Aldehydes to the Corresponding Carboxylic Acids by Molecular Oxygen
Molecules 2008, 13(4), 958-976; doi:10.3390/molecules13040958
Article

Synthesis and Biological Activity of Peptide Derivatives of Iodoquinazolinones/Nitroimidazoles

* ,  and
Received: 3 April 2008 / Revised: 18 April 2008 / Accepted: 19 April 2008 / Published: 24 April 2008
Download PDF [268 KB, uploaded 18 June 2014]

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. Quinazolinone; imidazole; 5-aminosalicylic acid; peptides; antimicrobial activity; anthelmintic activity.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
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.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert