title: Chrysin-benzothiazole conjugates as antioxidant and anticancer agents.
abstract: 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, (1)H NMR, (13)C NMR spectroscopy and elemental analysis.
authors.affiliation: Organic Research Laboratory, Department of Bioresources and Food Sciences, College of Life and Environmental Sciences, Konkuk University, Seoul, South Korea.
authors.forename: Bhupendra M
authors.initials: BM
authors.lastname: Mistry
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 783 71 Olomouc, Czech Republic. Electronic address: rahul.svnit11@gmail.com.
authors.forename: Rahul V
authors.initials: RV
authors.lastname: Patel
authors.affiliation: Organic Research Laboratory, Department of Bioresources and Food Sciences, College of Life and Environmental Sciences, Konkuk University, Seoul, South Korea.
authors.forename: Young-Soo
authors.initials: YS
authors.lastname: Keum
authors.affiliation: Organic Research Laboratory, Department of Bioresources and Food Sciences, College of Life and Environmental Sciences, Konkuk University, Seoul, South Korea.
authors.forename: Doo Hwan
authors.initials: DH
authors.lastname: Kim
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004285:Dogs; D004353:Drug Evaluation, Preclinical; D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D061985:Madin Darby Canine Kidney Cells; D015394:Molecular Structure
chemical_list: D000970:Antineoplastic Agents; D000975:Antioxidants; D052160:Benzothiazoles; D005419:Flavonoids; C043561:chrysin; C005465:benzothiazole
keywords: ABTS assay; Benzothiazole; Cervical cancer; Chrysin; DPPH assay; Ovarian cancer; SRB assay