title: Mitsunobu alkylation of cancerostatic 5-fluorouridine with (2E)-10-hydroxydec-2-enoic acid, a fatty acid from royal jelly with multiple biological activities.
abstract: 5-Fluorouridine (1) - a nucleoside antimetabolite with strong cancerostatic properties - was protected i) at the 2'- and 3'-OH groups with a heptan-4-ylidene residue and ii) at the 5'-OH group with a (4-methoxyphenyl)(diphenyl)methyl residue. This fully protected compound, 3, was submitted to a Mitsunobu reaction with the N-hydroxysuccinimide (NHS) ester, 5, of (2E)-10-hydroxydec-2-enoic acid (4) which gave nucleolipid 6. The latter was detritylated with Cl2 CHCOOH to yield the co-drug 7 as NHS ester.
authors.affiliation: Organic Chemistry I - Bioorganic Chemistry, Institute of Chemistry of New Materials, University of Osnabrück, Barbarastr. 7, DE-49069 Osnabrück.
authors.forename: Vanessa
authors.initials: V
authors.lastname: Ottenhaus
authors.affiliation: Organic Chemistry I - Bioorganic Chemistry, Institute of Chemistry of New Materials, University of Osnabrück, Barbarastr. 7, DE-49069 Osnabrück. Helmut.Rosemeyer@uos.de.
authors.forename: Helmut
authors.initials: H
authors.lastname: Rosemeyer
mesh_terms: D000478:Alkylation; D016588:Anticarcinogenic Agents / Q000737:chemistry* / Q000494:pharmacology; D005227:Fatty Acids / Q000737:chemistry* / Q000494:pharmacology; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry* / Q000494:pharmacology; D013388:Succinimides / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D000099219:Royal Jelly
chemical_list: D016588:Anticarcinogenic Agents; D005227:Fatty Acids; D005229:Fatty Acids, Monounsaturated; D013388:Succinimides; D014529:Uridine; D000099219:Royal Jelly; C001943:5-fluorouridine; C055543:10-hydroxy-2-decenoic acid; C001426:N-hydroxysuccinimide
keywords: (2E)-Dec-2-enoic acid, 10-hydroxy-; Mitsunobu alkylation; Nucleolipids; Royal jelly; Uridine, 5-fluoro-