Design, synthesis and computational studies of N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides as potent anti-melanogenic and tyrosinase inhibitors

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Abstract This manuscript describes the synthesis of some new N-(substituted-phenyl)-4-(4-phenyl-1-piperazinyl)butanamides (5a-c) through a facile bi-step strategy. The structures of these compounds were corroborated by their IR, EI-MS, 1H NMR, 13C NMR spectra along with CHN analysis data. The results of Mushroom tyrosinase in vitro inhibition revealed that all compounds were superb inhibitors of this enzyme and among them 5b was identified as the most active compound having IC50 value of 0.168 ± 0.057 μM, relative to the standard (16.841 ± 1.146 μM). The kinetic analysis (Ki = 0.22 μM) of this molecule revealed that it does not competitively inhibit the tyrosinase enzyme. It also significantly reduced (P