title: D-ring substituted rhazinilam analogues: semisynthesis and evaluation of antitubulin activity.
abstract: Novel (-)- and (+)-rhazinilam derivatives substituted on the D-ring (compounds 3, 4, 5 and 6) have been prepared from (+)-vincadifformine 7 and (-)-tabersonine and evaluated against the disassembly of microtubules into tubulin. Along with this study, a reproducible 'one pot' semisynthesis of (-)-rhazinilam 1 from (+)-1,2-didehydroaspidospermidine 2 was performed allowing the easy preparation of these new compounds.
authors.affiliation: Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Gif-sur-Yvette, France.
authors.forename: C
authors.initials: C
authors.lastname: Dupont
authors.forename: D
authors.initials: D
authors.lastname: Guénard
authors.forename: L
authors.initials: L
authors.lastname: Tchertanov
authors.forename: S
authors.initials: S
authors.lastname: Thoret
authors.forename: F
authors.initials: F
authors.lastname: Guéritte
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D018360:Crystallography, X-Ray; D066298:In Vitro Techniques; D007212:Indolizines; D007769:Lactams; D009682:Magnetic Resonance Spectroscopy; D008870:Microtubules / Q000187:drug effects; D008958:Models, Molecular; D013329:Structure-Activity Relationship; D050257:Tubulin Modulators
chemical_list: D000470:Alkaloids; D007212:Indolizines; D007769:Lactams; D050257:Tubulin Modulators; C009170:rhazinilam