Side chain modified sterols as probes into insect molting hormone metabolism. II: synthesis of monofluorocholesterols.
The hydroxylations of the cholesterol side chain at C-20, 22, and 25 are key terminal events in ecdysone biogenesis. We have prepared the C-20, C-22, C-24, and C-25 monofluorinated cholesterols as potential inhibitors of these hydroxylation events, and preliminary bioassay results in Manduca sexta are reported. The synthesis of [26(14)C]-20-fluorocholesterol is also described. Although the 20-, 22-, and 25-monofluorocholesterols do not appear to affect larval growth and development, the 24-fluoro isomer shows a moderate retardation of growth and a modest increase in mortality.
D000818:Animals; D002250:Carbon Radioisotopes; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D002849:Chromatography, Gas; D004440:Ecdysone / Q000096:biosynthesis*; D007814:Larva / Q000187:drug effects / Q000378:metabolism; D007915:Lepidoptera / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D009036:Moths / Q000378:metabolism*; D013259:Steroids, Fluorinated / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D013329:Structure-Activity Relationship
D002250:Carbon Radioisotopes; D013259:Steroids, Fluorinated; D004440:Ecdysone; D002784:Cholesterol