138222-83-0Relevant academic research and scientific papers
β-AMINOMETHYLATION REACTIONS INVOLVING N-AZAHETEROARYL-SUBSTITUTED 2,5-DIMETHYLPYRROLES: UNUSUAL EFFECTS OF α-AZA GROUPS
Biava, Mariangela,Fioravanti, Rossella,Porretta, Giulio Cesare,Mencarelli, Paolo,Sleiter, Giancarlo
, p. 9 - 16 (2007/10/02)
The reactions of a number of N-aryl- and N-α-azaheteroaryl-substituted 2,5-dimethylpyrroles with Mannich reagents formed by formaldehyde and a secondary cyclic amine have been investigated in aqueous acetic acid at various temperatures and different Mannich reagent : pyrrole ratios.Using a 1:1 Mannich reagent : pyrrole molar ratio, all the pyrroles investigated cleanly afforded the corresponding single Mannich bases, with the exception of the N-(2-pyrimidinyl) derivative which, in its reaction with the morpholine Mannich reagent, always gave the double Mannich base, unless the reaction was stopped after a few minutes.On the other hand, even in the presence of a large excess of the Mannich reagents, it proved impossible to bisaminoalkylate the N-aryl-2,5-dimethylpyrrole derivatives, whatever the amine and the reaction conditions adopted, and the N-heteroaryl-2,5-dimethylpyrroles when the amine was the 4-methylpiperazine, double substitution being achieved only with performed Mannich salts.An explanation is offered for these unprecedented substituent and reagent effects in heteroaromatic aminoalkylation reactions.
Study of the Mannich reaction: β-amino-methylation of N-aryl and N-azaheteroaryl-substituted 2,5-dimethylpyrroles, compounds with potential biological activity
Biava,Fioravanti,Porretta,Frachey,Mencarelli,Sleiter,Perazzi,Simonetti,Villa
, p. 431 - 438 (2007/10/02)
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 easy-to-perform structural modifications in order to meet the requirement of bypassing resistance phenomena. This paper reports on the synthesis of several N-(α-azaheteroaryl)-substituted 2,5-dimethyl-pyrroles bearing in one β-position (or in both β-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.
Studies on anti-Candida agents with a pyrrole moiety. Synthesis and microbiological activity of some 3-aminomethyl-1,5-diaryl-2-methyl-pyrrole derivatives
Cerreto,Villa,Retico,Scalzo
, p. 701 - 708 (2007/10/02)
The synthesis and anti-Candida activity of some 3-aminomethyl-1,5-diaryl-2-methyl-pyrrole derivatives are reported. Some derivatives show a rather strong anti-Candida activity. On the basis of experimental results, microbiological activity of 1,5-diarylpy
