Amino acid derivatives. Part 5. Synthesis and anti-HIV activity of new sebacoyl precursor derived thioureido-amino acid and phthalimide derivatives

Abstract

A series of sebacoyl N,N-bis(substituted-alkyl-2-thioureido)alkyl carboxylic acid or ester derivatives 3-12 bearing an amino acid ester residue were prepared by a one-pot sequential reaction of sebacoyl chloride 1 with NH4SCN and amino acid or their ester hydrochlorides. Analogously, the sebacoyl-phthalimido derivatives 16 and 17 were prepared from treatment of 1 with phthalimide precursors. Treatment of 5 and 7 with Br2 in acetone furnished the iminothiazole analogues 18 and 19, respectively. Compounds 5, 6, 8-11 and 16 have been selected for their inhibitory activity screening against HIV-1 and HIV-2 in MT-4 cells.