Chrysin-benzothiazole conjugates as antioxidant and anticancer agents

Area of Science:

• Medicinal Chemistry
• Organic Synthesis
• Pharmacology

Background:

• Chrysin derivatives are explored for therapeutic potential.
• Benzothiazole scaffolds are known for diverse biological activities.
• Developing novel anticancer agents with antioxidant properties is crucial.

Purpose of the Study:

• Synthesize novel 7-(4-bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one analogues.
• Evaluate the antioxidant and anticancer activities of synthesized compounds.
• Identify structure-activity relationships for improved drug design.

Main Methods:

• Synthesis of 6-substituted 2-aminobenzthiazoles and their coupling with a chrysin derivative.
• Antioxidant activity assessed using DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) assays.
• Anticancer activity evaluated against HeLa, CaSki (cervical), and SK-OV-3 (ovarian) cancer cell lines using the SRB (Sülfobarbitursäure) assay.
• Cytotoxicity assessed using Madin-Darby canine kidney (MDCK) cells.

Main Results:

• Compounds 6a-r exhibited significant antioxidant activity, comparable to ascorbic acid, especially halogenated analogues (6g, 6h, 6j-6l).
• Compounds 6a and 6r showed potent activity against the HeLa cell line.
• Compound 6g (chlorine) and 6k (di-fluoro) were effective against CaSki cells.
• Compounds 6j (mono-fluoro) and 6o (ketonic) displayed significant anticancer effects against the SK-OV-3 cell line.

Conclusions:

• The synthesized benzothiazole-chrysin analogues possess promising antioxidant and anticancer properties.
• Halogen substitutions and specific functional groups on the benzothiazole ring are critical for modulating biological activity.
• These findings provide a basis for developing new therapeutic agents targeting cervical and ovarian cancers.