Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
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The microwave assisted reaction between heterocyclic o-aminonitriles 1 and
cyclic ketones 2 catalyzed by zinc chloride led to new series of pyrazolo[3,4-b]
[1,8]naphthyridin-5-amines 3 in good yields. This procedure provides several advantages
such as being environmentally friendly, high yields, simple work-up procedure, broad
scope of applicability and the protocol provides an alternative for the synthesis of
pyrazolonaphthyridines. The whole series showed antifungal activities against
Candida albicans and Cryptococcus neoformans standardized strains, being compounds
with a 4-p-tolyl substituent of the naphthyridin scheleton (3a, 3d and 3g), the most active
ones mainly against C. albicans, which appear to be related to their comparative
hydrophobicity. Among them, 3d, containing a cyclohexyl fused ring, showed the best
activity. The anti-Candida activity was corroborated by testing the three most active
compounds against clinical isolates of albicans and non-albicans Candida strains. These
compounds were also screened by the US National Cancer Institute (NCI) for their ability
to inhibit 60 different human tumor cell lines. Compounds 3a and 3e showed remarkable antitumor activity against cancer cell lines, with the most important GI50 values ranging from 0.62 to 2.18 μM.
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