title: Synthesis and cytotoxicity of some new eriocalyxin B derivatives.
abstract: Eriocalyxin B (1) was regarded as the promising candidate for new anticancer agent because of its potent activity and novel mechanism of action. Systematic modifications of 1 were done, and nineteen derivatives were synthesized and their cytotoxicities against five tumor cell lines were evaluated. The structure-activity relationship (SAR) of 1 confirmed that the alpha,beta-unsaturated ketone moieties in ring A and D are the leading active sites; the 7,20-epoxy moiety, OH-6 and OH-7 play an important role in keeping the cytotoxicity. The 6,7-seco derivative 19 had remarkable activity while derivative 20 oxidized from 19 was completely inactive, which suggested that the carboxyl group could destroy the cytoxicity of 20 despite the presence of alpha,beta-unsaturated ketone moiety.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Longquan Road 610, Kunming 650204, Yunnan, People's Republic of China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhao
authors.forename: Xue-Mei
authors.initials: XM
authors.lastname: Niu
authors.forename: Li-Ping
authors.initials: LP
authors.lastname: Qian
authors.forename: Ze-Yuan
authors.initials: ZY
authors.lastname: Liu
authors.forename: Qin-Shi
authors.initials: QS
authors.lastname: Zhao
authors.forename: Han-Dong
authors.initials: HD
authors.lastname: Sun
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D020128:Inhibitory Concentration 50; D020014:K562 Cells; D008297:Male; D008958:Models, Molecular; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D004224:Diterpenes; C516552:eriocalyxin B