Synthesis and anticancer evaluation of naphthoquinone esters with 2'-cyclopentyl and 2'-cyclohexyl substituents.
Twelve novel naphthoquinone esters containing cyclopentyl and cyclohexyl substituents at C-2' of the propyl chain were synthesized by starting from 1-hydroxy-2-naphthoic acid via alkylation with cyclopentyl ester and cyclohexyl ester. They were evaluated for cytotoxicity against three cancer cell lines (human epidermoid carcinoma (KB), human cervical carcinoma (HeLa), and human hepatocellular carcinoma (HepG(2))). In comparison to naphthoquinone esters with the 2',2'-dimethyl group, the naphthoquinones with a 2'-cyclopentyl substituent showed stronger activity than those with a 2'-cyclohexyl substituent, but less than that with the 2',2'-dimethyl group. This work provides new information about the effect of 2'-position substituents on the cytotoxicity of naphthoquinone ester analogues.
Natural Products and Organic Synthesis Research Unit (NPOS), Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok, Thailand. fscinpk@ku.ac.th
Ngampong
N
Kongkathip
Narathip
N
Pradidphol
Komkrit
K
Hasitapan
Boonsong
B
Kongkathip
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D003510:Cyclohexanes / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D004952:Esters; D006801:Humans; D020128:Inhibitory Concentration 50; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000970:Antineoplastic Agents; D003510:Cyclohexanes; D003517:Cyclopentanes; D004952:Esters; D009285:Naphthoquinones; C506365:Cyclohexane