title: Synthesis and biological evaluation of oseltamivir analogues from shikimic acid.
abstract: New oseltamivir analogues were designed and synthesized, starting from shikimic acid. Biological evaluation against three human cancer cell lines (KB, MCF7 and Lu-1) showed that many of them exhibited cytotoxic activity. Azides 5 are more active than the corresponding amines 6. Thus, the reduction of the azide group into amine led to the loss of cytotoxicity. The compounds with a cyclohexanemethyloxy group at C-3 were more active than the other investigated compounds belonging to the same series. This cyclohexanemethyloxy group seems to be critical for the cytotoxic activity of this class of compounds. The synthetic oseltamivir analogues 6a-e had no inhibition activity, even at the concentration of 50 microM when they were evaluated for their in vitro influenza A neuraminidase inhibitory activity by an enzymatic assay.
authors.forename: Van Hung
authors.initials: VH
authors.lastname: Nguyen
authors.forename: Van Cuong
authors.initials: VC
authors.lastname: Pham
authors.forename: Thi Thao
authors.initials: TT
authors.lastname: Do
authors.forename: Huong Doan Thi
authors.initials: HD
authors.lastname: Mai
authors.forename: Nguyen Thanh
authors.initials: NT
authors.lastname: Le
authors.forename: Van Nam
authors.initials: VN
authors.lastname: Vu
authors.forename: Van Hieu
authors.initials: VH
authors.lastname: Tran
authors.forename: Thi Minh Hang
authors.initials: TM
authors.lastname: Nguyen
authors.forename: Wim
authors.initials: W
authors.lastname: Dehaen
authors.forename: Van Minh
authors.initials: VM
authors.lastname: Chau
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D015394:Molecular Structure; D053139:Oseltamivir / Q000031:analogs & derivatives* / Q000737:chemistry*; D012765:Shikimic Acid / Q000737:chemistry*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D053139:Oseltamivir; D012765:Shikimic Acid