Medicinal Chemistry

Synthesis and Antioxidant Activity of Novel Series of Naphthoquinone Derivatives Attached to Benzothiophene Moiety

Abstract

Moustafa A Gouda, Hadeer Fakhr Eldien, Margret M Girges and Moged A Berghot

A series of aryl azonaphthoquinones 8a-e were obtained via coupling of the corresponding diazonium salts 7a-c with naphthoquinones 2 or 3 in pyridine. Moreover, treatment of 5 with 6a, b in ethanol containing potassium carbonate afforded the corresponding enaminones 9a, b, respectively. Furthermore, heating of 6a with 2-hydroxy-3-((piperidn- 1-yl)methyl)naphthalene-1,4-dione 10 in EtOH/AcOHor sodium 3,4-dihydro-3,4-dioxonaphthalene-1-sulphonate 1 in MeOH/H2O afforded the corresponding enaminones 11 and 12, respectively. The newly synthesized compounds were screened for their antioxidant activity. Compounds 8b 89.87, 9a (89.93%) and 9b (95.97%) exhibited promising activities. On the other hand compounds 8b, 9a, 9b, 11 and 12 have the ability to protect DNA from the damage induced by bleomycin.