Synthesis and Biological Activity of 4-Amino-1-Methyl-5-Imidazolecarboxylic Acid Derivatives

Title: Synthesis and Biological Activity of 4-Amino-1-Methyl-5-Imidazolecarboxylic Acid Derivatives

Volume: 3 Issue: 3

Author(s): A. Regiec, H. Mastalarz, R. Miedzybrodzki, K. Smietanska and R. Jasztold-Howorko

Affiliation:

• Department of OrganicChemistry, Faculty of Pharmacy, Medical Academy of Wroclaw, ul.Grodzka 9, 50-137 Wroclaw, Poland.,Poland

Keywords: Imidazoles, anti-inflammatory, nitric oxide, cytokines, cytotoxicity

Abstract: The main goal of our study was the synthesis and biological evaluation of 4-amino- and 4-[(4- chlorobenzoyl)amino]-1-methylimidazole N-substituted 5-carboxamides. Biological in vitro tests indicated their remarkable influence on some cellular immune and inflammatory responses compared with ibuprofen and leflunomide as reference drugs. The toxicity of the tested compounds on murine bone marrow cells was also determined. The anti-inflammatory activity of 4-[(4-chlorobenzoyl)amino]-5-[N-(4-chlorophenyl)]-1-methyl- 5-imidazolecarboxamide (7a) was confirmed in vivo in the carrageenan-induced oedema test. Comparison of the biological activity of 7a with that of the isosteric isothiazole derivative MR-2/94 suggests that replacement of the isothiazole core ring system with an imidazole one resulted in a considerable lowering of toxicity while maintaining anti-inflammatory and immunotropic properties.

Cite this article as:

Regiec A., Mastalarz H., Miedzybrodzki R., Smietanska K. and Jasztold-Howorko R., Synthesis and Biological Activity of 4-Amino-1-Methyl-5-Imidazolecarboxylic Acid Derivatives, Letters in Drug Design & Discovery 2006; 3(3) . https://dx.doi.org/10.2174/157018006776286961