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RING OPENING OF COUMARIN DERIVATIVES WITH NITROGEN NUCLEOPHILIC REAGENTS AND THEIR BIOLOGICAL ACTIVITY

Elsherbiny. H. El-Sayed , Mohamed. Abd El-Moneim , Ibrahim. M. El-Deen , Ahmed. M. Mossalam

1,2-Bis[(o-hydroxy-1-naphthaldiene)amino]-ethane 3, 2-hydroxy-1-naphthaldazine 4 and thiosemicarbazone derivative 6 were prepared by ring opening of coumarin derivatives 2a,b and 10 with ethylenediamine, hydrazine hydrate and thiosemicarbazide. Acetylation of compounds 4 and 6 give 2-acetoxy-1-naphthaldazine 5 and triacetyl 7 derivatives. 5-Bromo salicylaldazine 11 was prepared via ring opening of 5-bromo-3-benzoylamino coumarin 9 with hydrazine hydrate. The mass spectral fragmentation patterns of some prepared compounds were investigated to elucidate the structure of the synthesized compounds. Biological studies of some prepared compounds were carried out to investigate their antioxidant and anticancer activities. It was found that compounds 4, 7 and 11 were active against antioxidant. Compounds 7 and 11 were also highly active against MCF-7 and HEPG-2 cell lines.