Syntheses and biological activity studies of novel sterol analogs from nitroso Diels-Alder reactions of ergosterol

Baiyuan Yang; Patricia A Miller; Ute Möllmann; Marvin J Miller

doi:10.1021/ol900997t

Syntheses and biological activity studies of novel sterol analogs from nitroso Diels-Alder reactions of ergosterol

Org Lett. 2009 Jul 2;11(13):2828-31. doi: 10.1021/ol900997t.

Authors

Baiyuan Yang¹, Patricia A Miller, Ute Möllmann, Marvin J Miller

Affiliation

¹ Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.

Abstract

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents* / chemical synthesis
Antineoplastic Agents* / chemistry
Antineoplastic Agents* / pharmacology
Drug Screening Assays, Antitumor
Ergosterol* / analogs & derivatives
Ergosterol* / chemical synthesis
Ergosterol* / chemistry
Ergosterol* / pharmacology
Female
Humans
Male
Molecular Structure
Nitroso Compounds / chemistry*
Stereoisomerism

Substances

Antineoplastic Agents
Nitroso Compounds
Ergosterol

Abstract

Publication types

MeSH terms

Substances

Grants and funding