Abstract
AbstractThe present work demonstrates the utility of enamines as building blocks for the synthesis of pyrazoles and pyrimidines through efficient procedures. Thus, the reactivity of pyrimidinone‐based enamines 1 a,b towards carbon nucleophiles such as acetylacetone, malononitrile and ethyl cyanoacetate to produce various 1,3‐difunctionalized products has been investigated. Accordingly, a series of new pyrazoles and pyrimidines based on pyrimidinone were prepared and characterized by a variety of synthetic routes through the reactions of 1,3‐difunctionalized products with hydrazine hydrate, urea and guanidine hydrochloride. In vitro biological studies such as cytotoxicity, antioxidant and bleomycin‐dependent DNA damage were screened. Compounds 3 b, 4 b, 7 a‐9 b and 13 a,b displayed wonderful and distinctive activities against the cancer cell line (HepG2), accompanied by mild effects on non‐tumorigenic cells (WI‐38). The antioxidant behaviour of compounds 7 a, 8 a, 9 a, 11 a and 13 a,b has shown a free radical scavenging activity close or superior to vitamin C (reference drug), using the ABTS method. Moreover, the most potent cytotoxic and antioxidant compounds have been demonstrated the pre‐eminent protective impact to DNA against the damage caused by bleomycin.
Published Version
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