Chrysin-benzothiazole conjugates as antioxidant and anticancer agents

0451908 - ÚEB 2016 RIV GB eng J - Journal Article
Mistry, B.M. - Patel, Rahul V. - Keum, Y.S. - Kim, D.H.
Chrysin-benzothiazole conjugates as antioxidant and anticancer agents.
Bioorganic and Medicinal Chemistry Letters. Roč. 25, č. 23 (2015), s. 5561-5565. ISSN 0960-894X. E-ISSN 1464-3405
R&D Projects: GA MŠMT(CZ) LO1204
Institutional support: RVO:61389030
Keywords : Chrysin * Benzothiazole * Cervical cancer
Subject RIV: EB - Genetics ; Molecular Biology
Impact factor: 2.486, year: 2015

7-(4-Bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one, obtained from chrysin with 1,4-dibromobutane, was combined with a wide range of 6-substituted 2-aminobenzthiazoles, which had been prepared from the corresponding anilines with potassium thiocyanate. Free radical scavenging efficacies of newer analogues were measured using DPPH and ABTS assays, in addition to the assessment of their anticancer activity against cervical cancer cell lines (HeLa and CaSki) and ovarian cancer cell line (SK-OV-3) implementing the SRB assay. Cytotoxicity of titled compounds was checked using Madin-Darby canine kidney (MDCK) non-cancer cell line. Overall, 6a-r indicated remarkable antioxidant power as DPPH center dot and ABTS(center dot+) scavengers; particularly the presence of halogen(s) (6g, 6h, 6j-6l) was favourable with IC50 values comparable to the control ascorbic acid. Unsubstituted benzothiazole ring favored the activity of resultant compounds (6a and 6r) against HeLa cell line, whereas presence of chlorine (6g) or a di-fluoro group (6k) was a key to exert strong action against CaSki. Moreover, a mono-fluoro (6j) and a ketonic functionality (6o) were beneficial to display anticipated anticancer effects against ovarian cancer cell line SK-OV-3. The structural assignments of the new products were done on the basis of IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis.
Permanent Link: http://hdl.handle.net/11104/0252959