Régis Le Guillou

Synthesis and antimicrobial activities of N-substituted imides.

In the field of our research programs concerning novel antimicrobial agents, a series of N-substituted imides was synthesized. These compounds were obtained by cyclization of amido-acids in acetic anhydride/sodium acetate or hexamethyldisilazane/zinc bromide for the hydroxy-aromatic derivatives. The hydroxy-alkyl maleimides were directly prepared by condensation of the corresponding amino-alcohol with maleic anhydride in boiling toluene. Most of N-substituted maleimides showed an interesting antimicrobial activity towards bacteria from the ATCC collection (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) but the MIC values for P. aeruginosa were always high (128 microg/ml). The imides with alkyl substituents showed higher activities than aromatic analogues with MIC values in the range of 8-32 microg/ml. Comparatively, succinimides were practically inactive.

A survey of mono- or bis-decarboxylation of β-methyl polyethylenic-malonic acids

Diverse experimental conditions, leading to mono- or bis-decarboxylation of β-methyl polyethylenic-malonic acids, were examined. A clean and easy bis-decarboxylation was reported.

A new one-pot synthesis of all E-retinoic acid via a new enaminodiester synthon

A ‘one-pot’ synthesis of all E-retinoic acid from a new enaminodiester was described. The enaminodiester was easily produced from methyl isopropylidenemalonate and DMF-DMA.