title: Synthesis and biological activity of novel epothilone aziridines.
abstract: [reaction: see text]. A series of 12alpha,13alpha-aziridinyl epothilone derivatives were synthesized in an efficient manner from epothilone A. The final semisynthetic route involves a formal double-inversion of stereochemistry at both the C12 and C13 positions. All aziridine analogues were tested for effects on tubulin binding polymerization and cytotoxicity. The results indicate that the aziridine moiety is a viable isosteric replacement for the epoxide in the case of epothilones.
authors.affiliation: Division of Discovery Chemistry, The Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 4000, Princeton, New Jersey 08543-4000, USA. alicia.regueiroren@bms.com
authors.forename: A
authors.initials: A
authors.lastname: Regueiro-Ren
authors.forename: R M
authors.initials: RM
authors.lastname: Borzilleri
authors.forename: X
authors.initials: X
authors.lastname: Zheng
authors.forename: S H
authors.initials: SH
authors.lastname: Kim
authors.forename: J A
authors.initials: JA
authors.lastname: Johnson
authors.forename: C R
authors.initials: CR
authors.lastname: Fairchild
authors.forename: F Y
authors.initials: FY
authors.lastname: Lee
authors.forename: B H
authors.initials: BH
authors.lastname: Long
authors.forename: G D
authors.initials: GD
authors.lastname: Vite
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004852:Epoxy Compounds / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001388:Aziridines; D004852:Epoxy Compounds