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Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid

Publication date:

September 2018


Source:Bioorganic Chemistry, Volume 79

Author(s): Pervaiz Ali Channar, Aamer Saeed, Fayaz Ali Larik, Bakhtawar Batool, Saima Kalsoom, M.M Hasan, Mauricio F. Erben, Hesham R. El-Seedi, Musrat Ali, Zaman Ashraf

Aryl pyrazoles are well recognized class of heterocyclic compounds found in several commercially available drugs. Owing to their significance in medicinal chemistry, in this current account we have synthesized a series of suitably substituted aryl pyrazole by employing Suzuki cross-coupling reaction. All compounds were evaluated for inhibition of mushroom tyrosinase enzyme both in vitro and in silico. Compound 3f (IC50 = 1.568 ± 0.01 µM) showed relatively better potential compared to reference kojic acid (IC50 = 16.051 ± 1.27 µM). A comparative docking studies showed that compound 3f have maximum binding affinity against mushroom tyrosinase (PDBID: 2Y9X) with binding energy value (−6.90 kcal/mol) as compared to Kojic acid. The 4-methoxy group in compound 3f shows 100% interaction with Cu. Compound 3f displayed hydrogen binding interaction with His61 and His94 at distance of 1.71 and 1.74 Å which might be responsible for higher activity compared to Kojic acid.
Graphical abstract




Authors:   Author(s): Pervaiz Ali Channar, Aamer Saeed, Fayaz Ali Larik, Bakhtawar Batool, Saima Kalsoom, M.M Hasan, Mauricio F. Erben, Hesham R. El-Seedi, Musrat Ali, Zaman Ashraf
Journal:   Bioorganic Chemistry
Volume:   79
Year:   2018
Pages:   293
DOI:   10.1016/j.bioorg.2018.04.026
Publication date:   11-Jun-2018
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