Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: Structure–activity relationship

2,4,5-Trimethoxy chalcones and analogues were synthesized from asaronaldehyde derived from β-asarone. These novel compounds when tested against three human tumour cell lines (MCF-7, SW-982 and HeLa) using MTT assay, revealed that chalcones possessing electron donor groups in para position to carbonyl moiety of phenyl ring A, showed better inhibitory activity (2, 3, 4, 6, 7, 10, 17). When evaluated for antioxidant activities, compound 15 exhibited better free radical scavenging property in DPPH assay while compounds 2, 3, 5, 7, 9, 10, 11, 16, and 18 showed significant NO scavenging activity. All compounds exhibited very good phenyl hydrazine induced haemolysis of erythrocytes in phenylhydrazine assay. Structure–activity relationship (SAR) study using in-silico analysis matched well with in-vitro tumour cell inhibitory activity.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Synthesized series of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde. ► All these compounds were tested in-vitro inhibitory activities against human tumour cell lines. ► Chalcones that are having electron donor groups in para position to aromatic moiety of phenyl ring exhibited high activity. ► All compounds were evaluated for antioxidant property.