One‐Pot Laccase‐Catalysed Synthesis of 5,6‐Dihydroxylated Benzo[b]furans and Catechol Derivatives,and Their Anticancer Activity |
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Authors: | Kevin W Wellington Tozama Qwebani‐Ogunleye Natasha I Kolesnikova Dean Brady Charles B de Koning |
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Institution: | 1. CSIR Biosciences, Pretoria, South Africa;2. Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Wits, South Africa |
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Abstract: | A commercial laccase, Suberase® from Novozymes, was used to catalyse the synthesis of 5,6‐dihydroxylated benzob]furans and catechol derivatives. The yields were, in some cases, similar to or better than that obtained by other enzymatic, chemical or electrochemical syntheses. The synthesised derivatives were screened against renal (TK10), melanoma (UACC62), breast (MCF7) and cervical (HeLa) cancer cell lines. GI50, TGI and LC50 are reported for the first time. Anticancer screening showed that the cytostatic effects of the 5,6‐dihydroxylated benzob]furans were most effective against the melanoma (UACC62) cancer cell line with several compounds exhibiting potent growth inhibitory activities (GI50 = 0.77–9.76 µM), of which two compounds had better activity than the anticancer agent etoposide (GI50 = 0.89 µM). One compound exhibited potent activity (GI50 = 9.73 µM) against the renal (TK10) cancer cell line and two exhibited potent activity (GI50 = 8.79 and 9.30 µM) against the breast (MCF7) cancer cell line. These results encourage further studies of the 5,6‐dihydroxylated benzob]furans for their potential application in anticancer therapy. |
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Keywords: | 1 3‐Dicarbonyls Anticancer Benzo[b]furans Biocatalysis Catechols C?C coupling Cytostatic effects Cytotoxic effects GI50 LC50 Laccase Michael addition TGI |
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