Potent antitumor activity of synthetic 1,2-Naphthoquinones and 1,4-Naphthoquinones.
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.
Kongkathip
Ngampong
N
Natural Products and Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand. fscinpk@ku.ac.th
Kongkathip
Boonsong
B
Siripong
Pongpun
P
Sangma
Chak
C
Luangkamin
Suwaporn
S
Niyomdecha
Momad
M
Pattanapa
Suppachai
S
Piyaviriyagul
Suratsawadee
S
Kongsaeree
Palangpon
P
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
D000970:Antineoplastic Agents; D001578:Benzopyrans; D005663:Furans; D009285:Naphthoquinones; D011714:Pyrans; C420690:rhinacanthone