Study of the Mannich reaction: beta-amino-methylation of N-aryl and N-azaheteroaryl-substituted 2,5-dimethylpyrroles, compounds with potential biological activity

Farmaco. 1995 Jun;50(6):431-8.

Abstract

Owing to the increasing need of drugs for the treatment of a variety of fungal and bacterial opportunistic infections, a study has been started with the aim of synthesizing structures amenable to a number of easily-to-perform structural modifications in order to meet the requirement of bypassing resistance phenomena. This paper reports on the synthesis of several N-(alpha-azaheteroaryl)-substituted 2,5-dimethyl-pyrroles bearing in one beta-position (or in both beta-positions) aminomethyl groups, introduced via a Mannich reaction. Electronic and steric effects 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 bacteria, and several pathogenic plant fungi.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents
  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / pharmacology
  • Bacteria / drug effects*
  • Candida / drug effects
  • Chemical Phenomena
  • Chemistry, Physical
  • Fungi / drug effects*
  • Mannich Bases / chemical synthesis
  • Mannich Bases / pharmacology
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacology
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / pharmacology
  • Pyrroles / chemical synthesis*
  • Pyrroles / pharmacology
  • Thiazoles / chemical synthesis*
  • Thiazoles / pharmacology

Substances

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Mannich Bases
  • Pyridines
  • Pyrimidines
  • Pyrroles
  • Thiazoles