Syntheses and biological activity studies of novel sterol analogs from nitroso Diels-Alder reactions of ergosterol.
A series of novel sterol analogs was prepared using nitroso Diels-Alder reactions with ergosterol. Most cycloaddition reactions proceeded in an excellent regio- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity in PC-3 and MCF-7 cancer cell lines.
Yang
Baiyuan
B
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Miller
Patricia A
PA
Möllmann
Ute
U
Miller
Marvin J
MJ
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004875:Ergosterol / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D006801:Humans; D008297:Male; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D009603:Nitroso Compounds; D004875:Ergosterol