Synthesis and evaluation of antioxidant and antitumor activity of some heterocyclic benzocoumarin derivatives
1-[(Bezocoumarin-3-ylethylidene)amino]-thiourea (2) was prepared via condensation of 3-acetyl benzocoumarin (1) with thiosemicarbazide, Reaction of compound 2 with acetic anhydride and ethyl chloroacetate in the presense of fused sodium acetate gives N-triacetyl derivatives (3) and 3-[(bezocoumarin-3-ylethylidene)amino]-4- oxo-imidazolidin-2-thione (4).Treatment of 4 with aromatic aldehydes yielding the corresponding 3-substituted-4-oxo- 5-arylidene-imidazolidin-2-thiones (5a, b). Acetylation of compounds 4 and 5 with acetic anhydride afforded the corresponding 1-acetyl-3-substituted-imidazolidin-2-thione (6) and 1-acetyl-3-substituted-5-arylidene-imidazolidine-2- thiones (7a, b), respectively. Acetylation of 4 with acetic anhydride in presence of fused sodium acetate gives 1, 5- diacetyl-3-substituted-imidazolidin-2-thione (8). The mass spectral fragmentation patterns of some prepared heterocyclic benzocoumarin derivatives have investigated in order to elucidate the structure of the synthesized compounds. The biological activity studies of heterocyclic benzocoumarins were carried out against antioxidant and antitumor activities.
Ibrahim M. El- Deen, Jehan A. Hasanen and Maha El-Ashery