Novel 3‐aryl‐5‐substituted‐coumarin analogues: Synthesis and bioactivity profile

Eighteen 3‐aryl‐5‐substituted‐coumarins—six 5‐acetyloxy‐derivatives, six 5‐hydroxy‐derivatives, and six 5‐geranyloxy‐derivatives—were synthesized, structurally characterized and their antioxidant activity, lipoxygenase inhibitory ability, as well as their cytotoxic activity against human neuroblasto...

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Published in:Drug development research 2020-06, Vol.81 (4), p.456-469
Main Authors: Kavetsou, Eleni, Katopodi, Annita, Argyri, Letta, Chainoglou, Eirini, Pontiki, Eleni, Hadjipavlou‐Litina, Dimitra, Chroni, Angeliki, Detsi, Anastasia
Format: Article
Language:English
Subjects:
acetyloxy‐moiety
Adenocarcinoma
Allosteric properties
Antioxidants
Aromatic compounds
Biological activity
Biotechnology
Coumarin
coumarins
Cytotoxic agents
Cytotoxicity
Derivatives
Lipoxygenase
molecular modeling
oxyprenylated analogues
Soybeans
Substitutes
Tumor cell lines
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Summary:Eighteen 3‐aryl‐5‐substituted‐coumarins—six 5‐acetyloxy‐derivatives, six 5‐hydroxy‐derivatives, and six 5‐geranyloxy‐derivatives—were synthesized, structurally characterized and their antioxidant activity, lipoxygenase inhibitory ability, as well as their cytotoxic activity against human neuroblastoma SK‐N‐SH and HeLa adenocarcinoma cell lines were evaluated. The 5‐acetyloxy‐compounds 3a‐3f were found to be the best cytotoxic agents among all the compounds studied. The bromo‐substituted coumarins 3a and 3b were remarkably active against HeLa cell line showing IC50 1.8 and 6.1 μM, respectively. Coumarin 5e possessing a geranyloxy‐chain on position 5 of the coumarin scaffold presented dual bioactivity, while 5‐geranyloxy‐coumarin 5f was the most competent soybean lipoxygenase inhibitor of this series (IC50 10 μM). As shown by in silico docking studies, the studied molecules present allosteric interactions with soybean lipoxygenases.
ISSN:0272-4391
1098-2299
DOI:10.1002/ddr.21639