title: Semisynthesis of D-ring modified taxoids: novel thia derivatives of docetaxel.
abstract: Two novel 5(20)-thia analogues of docetaxel have been synthesized from 10-deacetylbaccatin III or taxine B and isotaxine B. The key step of these syntheses is the concomitant thietane ring formation and acetylation of the tertiary alcohol at C-4. Both compounds are less cytotoxic than docetaxel but have divergent activity on microtubule disassembly.
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS 91198 Gif sur Yvette Cedex, France.
authors.forename: L
authors.initials: L
authors.lastname: Mercklé
authors.forename: J
authors.initials: J
authors.lastname: Dubois
authors.forename: E
authors.initials: E
authors.lastname: Place
authors.forename: S
authors.initials: S
authors.lastname: Thoret
authors.forename: F
authors.initials: F
authors.lastname: Guéritte
authors.forename: D
authors.initials: D
authors.lastname: Guénard
authors.forename: C
authors.initials: C
authors.lastname: Poupat
authors.forename: A
authors.initials: A
authors.lastname: Ahond
authors.forename: P
authors.initials: P
authors.lastname: Potier
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology; D000077143:Docetaxel; D006801:Humans; D007202:Indicators and Reagents; D007624:KB Cells; D008870:Microtubules / Q000187:drug effects; D017239:Paclitaxel / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D043823:Taxoids
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D007202:Indicators and Reagents; D043823:Taxoids; D000077143:Docetaxel; D017239:Paclitaxel