title: Potent antitumor activity of synthetic 1,2-Naphthoquinones and 1,4-Naphthoquinones.
abstract: Rhinacanthone (1) and two 1,2-pyranonaphthoquinones (2,3) were synthesized and found to show very potent cytotoxicity against three cancer cell lines (KB, HeLa and HepG(2)) with IC(50) values of 0.92-9.63 microM, whereas the corresponding hydroxylated derivative 4 had reduced cytotoxicity (IC(50) values of 7.61-24.13 microM). Three 1,2-furanonaphthoquinone derivatives (5-7) were also synthesized with similar cytotoxicity as 1,2-pyranonaphthoquinones. In comparison to 1,2-naphthoquinones, six 1,4-naphthoquinones derivatives fused with pyran ring (8-10) and furan ring (11-13) were synthesized and they showed less cytotoxicity or inactive to the cancer cell lines. Moreover, compound 13 had significant cytotoxicity against HeLa cell line (IC(50) value of 9.25 microM) while it showed no toxic to vero cell.
authors.affiliation: Natural Products and Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand. fscinpk@ku.ac.th
authors.forename: Ngampong
authors.initials: N
authors.lastname: Kongkathip
authors.forename: Boonsong
authors.initials: B
authors.lastname: Kongkathip
authors.forename: Pongpun
authors.initials: P
authors.lastname: Siripong
authors.forename: Chak
authors.initials: C
authors.lastname: Sangma
authors.forename: Suwaporn
authors.initials: S
authors.lastname: Luangkamin
authors.forename: Momad
authors.initials: M
authors.lastname: Niyomdecha
authors.forename: Suppachai
authors.initials: S
authors.lastname: Pattanapa
authors.forename: Suratsawadee
authors.initials: S
authors.lastname: Piyaviriyagul
authors.forename: Palangpon
authors.initials: P
authors.lastname: Kongsaeree
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001578:Benzopyrans / Q000138:chemical synthesis / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology; D011714:Pyrans / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D001578:Benzopyrans; D005663:Furans; D009285:Naphthoquinones; D011714:Pyrans; C420690:rhinacanthone