title: Synthesis and biological evaluation of a natural ester sintenin and its synthetic analogues.
abstract: Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on alpha-glucosidase.
authors.affiliation: Department of Traditional Chinese Medicine and Natural Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310031, People's Republic of China.
authors.forename: Li Hong
authors.initials: LH
authors.lastname: Hu
authors.forename: Hong Bin
authors.initials: HB
authors.lastname: Zou
authors.forename: Jing Xu
authors.initials: JX
authors.lastname: Gong
authors.forename: Hai Bo
authors.initials: HB
authors.lastname: Li
authors.forename: Lei Xiang
authors.initials: LX
authors.lastname: Yang
authors.forename: Wei
authors.initials: W
authors.lastname: Cheng
authors.forename: Chang Xin
authors.initials: CX
authors.lastname: Zhou
authors.forename: Hua
authors.initials: H
authors.lastname: Bai
authors.forename: Françoise
authors.initials: F
authors.lastname: Guéritte
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhao
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004952:Esters / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D004952:Esters; D011422:Propionates; C499736:sintenin