title: Synthesis of 3'-methoxy-E-diethylstilbestrol and its analogs as tumor angiogenesis inhibitors.
abstract: 3'-Methoxy-E-diethylstilbestrol (2), with the structural and original similarities to 2-methoxyestradiol (2-ME2, 1), was synthesized and screened against HUVEC and a series of human cancer cell lines including RL95-2, SKOV-3, MCF-7 and T-47D in vitro. The configuration of the title compound was determined via the single crystal X-ray diffraction of its benzoyl-ester derivative (10). The fact that 3'-methoxy-E-diethylstilbestrol and its analogues (8 and 11) showed potential antiangiogenesis and anti-tumor activities at a close level, whereas its ester derivative (10) did not display any cytotoxic activities on all the screening cell lines indicated that the core scaffold of 3'-methoxy-3,4-diphenylhexane and the exposed hydroxyl-groups in the structures are essential pharmacophores for their anti-tumor activities.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, China.
authors.forename: Qian
authors.initials: Q
authors.lastname: Liu
authors.forename: Weiwei
authors.initials: W
authors.lastname: Jin
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhu
authors.forename: Jieyun
authors.initials: J
authors.lastname: Zhou
authors.forename: Min
authors.initials: M
authors.lastname: Lu
authors.forename: Qian
authors.initials: Q
authors.lastname: Zhang
mesh_terms: D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002478:Cells, Cultured; D004054:Diethylstilbestrol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D061307:Human Umbilical Vein Endothelial Cells / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D008956:Models, Chemical; D015394:Molecular Structure; D009369:Neoplasms / Q000098:blood supply / Q000188:drug therapy / Q000473:pathology; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction
chemical_list: C574200:3'-methoxy-E-diethylstilbestrol; D020533:Angiogenesis Inhibitors; D004054:Diethylstilbestrol