title: Fluorination of triptolide and its analogues and their cytotoxicity.
abstract: The reaction of triptolide and its analogues with a fluorinating agent, that is, bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor) or (diethylamino)sulfur trifluoride (DAST), was studied. One of the fluorinated products, 14beta-dehydroxy-14beta-fluoro triptolide, was found to be more cytotoxic than the parent natural triptolide.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy & Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Aoyagi
authors.forename: Yukio
authors.initials: Y
authors.lastname: Hitotsuyanagi
authors.forename: Tomoyo
authors.initials: T
authors.lastname: Hasuda
authors.forename: Saki
authors.initials: S
authors.lastname: Matsuyama
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Fukaya
authors.forename: Koichi
authors.initials: K
authors.lastname: Takeya
authors.forename: Ritsuo
authors.initials: R
authors.lastname: Aiyama
authors.forename: Takeshi
authors.initials: T
authors.lastname: Matsuzaki
authors.forename: Shusuke
authors.initials: S
authors.lastname: Hashimoto
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D045744:Cell Line, Tumor / Q000187:drug effects; D004048:Diethylamines / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004852:Epoxy Compounds / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D019073:HT29 Cells; D006801:Humans; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000494:pharmacology*; D008956:Models, Chemical; D010616:Phenanthrenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: C419465:(bis(2-methoxyethyl)amino)sulfur trifluoride; C529814:14-dehydroxy-14-fluorotriptolide; D000970:Antineoplastic Agents; D004048:Diethylamines; D004224:Diterpenes; D004852:Epoxy Compounds; D006845:Hydrocarbons, Fluorinated; D010616:Phenanthrenes; D013457:Sulfur Compounds; C001899:triptolide; D005461:Fluorine; C040394:diethylaminosulfur trifluoride; D005459:Fluorides