SYNTHESIS AND TRANSFORMATION OF TETRAHYDRONAPHTHO [2,1-d] ИЗОINDOLES FROM THE DITERPENOID MALEOPIMARATE. EVALUATION OF ANTIBACTERIAL ACTIVITY IN VITRO
Keywords:
diterpenoids, maleopimaric acid, ureidoesters, cyclic amidines, Lossen rearrangement, Mannich reaction, azide-alkyne cycloaddition.Abstract
The Lossen rearrangement of N-hydroxyimide toluenesulfonate of methyl maleopimarate in the presence of amines proceeds with high regio- and stereoselectively and produces diterpenoid ureidoesters. The treatment of ureidoesters which with POCl3 afforded
tetrahydronaphtho[2,1-d]isoindoles. Under the proposed conditions, a diterpenoid ureidoester containing a propynyl substituent was synthesized and its selective catalytic transformations were studied. The newly synthesized compounds of tetrahydronaphtho[2,1-d]-isoindole structure 6c and 10a,c shown antibacterial activity against strains of Staphylococcus aureus and Bacillus cereus.
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