title: Asymmetric and highly stereoselective synthesis of the DEF-ring moiety of (-)-FR182877 and its derivative inducing mitotic arrest.
abstract: The asymmetric and highly stereoselective synthesis of compound 1, which corresponds exactly to the DEF-ring moiety of (-)-FR182877, and the biological activities of its derivatives are described. All derivatives of 1 showed no activity in the tubulin polymerization assay, but one derivative was shown to have the ability to induce mitotic arrest by interfering with microtubule dynamics, and the cellular effects are similar to those of paclitaxel.
authors.affiliation: Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Tokyo 169-8555, Japan.
authors.forename: Yu
authors.initials: Y
authors.lastname: Kobayakawa
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Mori
authors.forename: Hideki
authors.initials: H
authors.lastname: Okajima
authors.forename: Yasuhiko
authors.initials: Y
authors.lastname: Terada
authors.forename: Masahisa
authors.initials: M
authors.lastname: Nakada
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D006801:Humans; D008870:Microtubules / Q000187:drug effects; D008938:Mitosis / Q000187:drug effects*; D017239:Paclitaxel / Q000494:pharmacology; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D014404:Tubulin / Q000187:drug effects / Q000378:metabolism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; C408303:FR 182877; D011083:Polycyclic Compounds; D014404:Tubulin; D017239:Paclitaxel