STEREO SELECTIVE SYNTHESIS OF NOVEL LIGNAN INTERMEDIATES AS ANTIMICROBIAL AGENTS
Objectives: The aim of the present study was to synthesize a series of new lignan intermediates as potential antimicrobial agents.
Methods: Substituted benzene and aromatic acids or acid chlorides were converted to benzophenones 1(a-f). The benzophenones 1(a-f) on Stobbe condensation with and diethyl succinate in the presence of potassium t-butoxide yielded 4-(4-aryl)-4-(4-aryl)-3-ethoxycarbonyl-but-3-enoic acids (2a, 2f) and a mixture of E and Z-isomers of 4,4-diaryl-3-ethoxycarbonyl-but-3-enoic acids 2(b-e) and 3(b-e) in relatively good yields. The synthesized compounds were tested for their antimicrobial susceptibility against different fungi and bacteria species.
Results: The Stobbe condensation of benzophenones 1(a-f) and diethyl succinate in the presence of potassium t-butoxide yielded 4-(4-aryl)-4-(4-aryl)-3-ethoxycarbonyl-but-3-enoic acids (2a, 2f) and a mixture of E and Z-isomers of 4,4-diaryl-3-ethoxycarbonyl-but-3-enoic acids 2(b-e) and 3(b-e) in good yields. The compounds 1a and 1f yielded only 2a and 2f but not 3a and 3f due to symmetrical substitution in the aromatic rings. The structures of the new lignan intermediates were confirmed by spectral studies and elemental analysis.
Conclusions: Results of the antimicrobial activity reveal that some of the compounds particularly 2c, 2d, 3c and 3d act as potential antimicrobial agents different fungal and bacterial organisms.
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