Fluorination of triptolide and its analogues and their cytotoxicity.
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.
Aoyagi
Yutaka
Y
School of Pharmacy, Tokyo University of Pharmacy & Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Hitotsuyanagi
Yukio
Y
Hasuda
Tomoyo
T
Matsuyama
Saki
S
Fukaya
Haruhiko
H
Takeya
Koichi
K
Aiyama
Ritsuo
R
Matsuzaki
Takeshi
T
Hashimoto
Shusuke
S
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*
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