title: Total synthesis of novel D-ring-modified triptolide analogues: structure-cytotoxic activity relationship studies on the D-ring of triptolide.
abstract: The total synthesis of a trans-position butenolide analogue of triptolide 3 and the semi-synthesis of analogue 4, with a furan ring, and compound 5, without a planar D-ring, are described. Studies into the antitumor activity of these compounds suggest that the five-membered unsaturated lactone ring (D-ring) of triptolide is essential to its potent anticancer activity and the C18 carbonyl group may exert an important influence on the interaction between triptolide and the target molecule(s) responsible for initiating their cytotoxic effects.
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Road Zu Chong Zhi, Zhangjiang Hi-Tech Park, Shanghai, 201203, PR China.
authors.forename: Bing
authors.initials: B
authors.lastname: Zhou
authors.forename: Xiaomei
authors.initials: X
authors.lastname: Li
authors.forename: Huanyu
authors.initials: H
authors.lastname: Tang
authors.forename: Zehong
authors.initials: Z
authors.lastname: Miao
authors.forename: Huijin
authors.initials: H
authors.lastname: Feng
authors.forename: Yuanchao
authors.initials: Y
authors.lastname: Li
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004224:Diterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D005663:Furans / Q000737:chemistry; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D004224:Diterpenes; D004852:Epoxy Compounds; D005663:Furans; D010616:Phenanthrenes; C001899:triptolide; C039281:furan