title: Synthesis and biological evaluation of 7-O-modified oroxylin A derivatives.
abstract: Oroxylin A (5,7-dihydroxy-6-methoxyflavone) is a naturally occurring monoflavonoid isolated from the root of Scutellaria baicalensis Georgi, and exhibits potent anticancer activities in vitro and in vivo. In this study, we synthesized three series of oroxylin derivatives by connecting a nitrogen-containing hydrophilic, heterocyclic ring to the C7-OH via a varying length of carbon chain. All the derivatives were screened for anti-proliferative activities against three tumor cell lines. Some of the derivatives displayed higher activities compared to oroxylin A. The most potent antitumor compound, 5f, also induced apoptosis in HepG2 cell. The difference of 5f between the inhibiting rates of cell proliferation and the apoptotic rates indicated that 5f was more likely to be a necrosis-inducing agent or both apoptosis/necrosis inducer.
authors.affiliation: Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Fu
authors.forename: Jubo
authors.initials: J
authors.lastname: Wang
authors.forename: Liqin
authors.initials: L
authors.lastname: Yu
authors.forename: Li
authors.initials: L
authors.lastname: Zhao
authors.forename: Na
authors.initials: N
authors.lastname: Lu
authors.forename: Qidong
authors.initials: Q
authors.lastname: You
authors.forename: Qinglong
authors.initials: Q
authors.lastname: Guo
authors.forename: Zhiyu
authors.initials: Z
authors.lastname: Li
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D005419:Flavonoids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D056945:Hep G2 Cells; D006801:Humans; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D005419:Flavonoids; C080669:5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one