title: Synthesis and activity of oleanolic acid derivatives, a novel class of inhibitors of osteoclast formation.
abstract: Two series of oleanolic acid derivatives were synthesized and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1alpha,25-dihydroxy vitamin D3 was evaluated in a co-culture assay system. The structure-activity relationships, together with electronic structure based on the frontier molecular orbitals, for example, HOMO and LUMO, related to different amino acid substituents were studied. Derivatives with proline or phenylalanine showed a tendency to enhance the inhibitory activity.
authors.affiliation: Key Lab of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University 210093, PR China.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Zhang
authors.forename: Jian-xin
authors.initials: JX
authors.lastname: Li
authors.forename: Jianwei
authors.initials: J
authors.lastname: Zhao
authors.forename: Shao-zhong
authors.initials: SZ
authors.lastname: Wang
authors.forename: Yi
authors.initials: Y
authors.lastname: Pan
authors.forename: Ken
authors.initials: K
authors.lastname: Tanaka
authors.forename: Shigetoshi
authors.initials: S
authors.lastname: Kadota
mesh_terms: D000818:Animals; D066298:In Vitro Techniques; D051379:Mice; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D010010:Osteoclasts / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D009828:Oleanolic Acid