Chrysin–benzothiazole conjugates as antioxidant and anticancer agents

• Published in: Bioorganic & medicinal chemistry letters Vol. 25; no. 23; pp. 5561 - 5565
• Main Authors: Mistry, Bhupendra M., Patel, Rahul V., Keum, Young-Soo, Kim, Doo Hwan
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.12.2015; Elsevier
• Subjects: ABTS assay; Animals; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; Benzothiazole; Benzothiazoles - chemical synthesis; Benzothiazoles - chemistry; Benzothiazoles - pharmacology; Cell Line, Tumor; Cell Survival - drug effects; Cervical cancer; Chemistry; Chemistry, Medicinal; Chemistry, Organic; Chrysin; Dogs; DPPH assay; Drug Evaluation, Preclinical; Flavonoids - chemical synthesis; Flavonoids - chemistry; Flavonoids - pharmacology; HeLa Cells; Humans; Inhibitory Concentration 50; Life Sciences & Biomedicine; Madin Darby Canine Kidney Cells; Molecular Structure; Ovarian cancer; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; SRB assay; ABTS assay; Chrysin; Benzothiazole; DPPH assay; Cervical cancer; Ovarian cancer; SRB assay; DESIGN; ANTIBACTERIAL; ANTITUMOR-ACTIVITY; FREE-RADICALS; ANTIFUNGAL; DERIVATIVES
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2015.10.052

[Display omitted] 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 and ABTS+ 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, 1H NMR, 13C NMR spectroscopy and elemental analysis.