Design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents
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Two practical and efficient approaches have been implemented as alternative procedures
for the synthesis of naftifine and novel diversely substituted analogues 16 and 20 in good to
excellent yields, mediated by Mannich-type reactions as the key step of the processes. In these
approaches, the γ-aminoalcohols 15 and 19 were obtained as the key intermediates and their
subsequent dehydration catalyzed either by Brønsted acids like H2SO4 and HCl or Lewis acid
like AlCl3, respectively, led to naftifine, along with the target allylamines 16 and 20. The antifungal
assay results showed that intermediates 18 (bearing both a β-aminoketo- and N-methyl functionalities
in their structures) and products 20 were the most active. Particularly, structures 18b, 18c, and the
allylamine 20c showed the lowest MIC values, in the 0.5–7.8 µg/mL range, against the dermatophytes
Trichophyton rubrum and Trichophyton mentagrophytes. Interesting enough, compound 18b bearing
a 4-Br as the substituent of the phenyl ring, also displayed high activity against Candida albicans
and Cryptococcus neoformans with MIC80 = 7.8 µg/mL, being fungicide rather than fungistatic with
a relevant MFC value = 15.6 µg/mL against C. neoformans.
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