STUDY OF THE MANNICH REACTION - BETA-AMINO-METHYLATION OF N-ARYL AND N-AZAHETEROARYL-SUBSTITUTED 2,5-DIMETHYLPYRROLES, COMPOUNDS WITH POTENTIAL BIOLOGICAL-ACTIVITY

Owing to the increasing need of drugs for the treatment of a variety o f fungal and bacterial opportunistic infections, a study has been star ted with the aim of synthesizing structures amenable to a number of ea sily-to-perform structural modifications in order to meet the requirem ent of bypassing. resistance phenomena. This paper reports on the synt hesis of several N-(alpha-azaheteroaryl)-substituted 2,5-dimethyl-pyrr oles bearing in one beta-position (or in both beta-positions) aminomet hyl groups, introduced via a Mannich reaction. Electronic and steric e ffects by the N-(azaheteroaryl) substituents and the 2- and 5- methyl groups on the course of the Mannich reaction are discussed along with the results of in vitro tests against many Candida species, some bacte ria, and several pathogenic plant fungi.