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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
Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.
Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.
Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.
Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.
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2018 (English)In: Bioorganic chemistry (Print), ISSN 0045-2068, Vol. 79, p. 293-300Article in journal (Refereed) Published
Abstract [en]

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 mu M) showed relatively better potential compared to reference kojic acid (IC50 = 16.051 +/- 1.27 mu M). 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 angstrom which might be responsible for higher activity compared to Kojic acid.

Place, publisher, year, edition, pages
ACADEMIC PRESS INC ELSEVIER SCIENCE , 2018. Vol. 79, p. 293-300
Keywords [en]
Aryl pyrazoles, Suzuki cross coupling, In vitro Mushroom tyrosinase assay, Kojic acid, In silico Molecular docking studies
National Category
Medicinal Chemistry Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-360175DOI: 10.1016/j.bioorg.2018.04.026ISI: 000436773100032PubMedID: 29793142OAI: oai:DiVA.org:uu-360175DiVA, id: diva2:1247973
Available from: 2018-09-13 Created: 2018-09-13 Last updated: 2018-11-26Bibliographically approved

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El-Seedi, Hesham

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