Inhibitors of steroid biosynthesis: Chemical modification of the steroidal side chain

The enzyme Sterol Methyl Transferase (SMT) is essential to plants and fungi. Steroidal analogues have demonstrated the ability to effectively inhibit enzymes such as SMT, demonstrating both therapeutic and agrochemical significance. A series of side chain modified analogues of lanosterol were rationally designed and synthesized. In order to determine molecular parameters and to gain mechanistic detail, groupings of compounds were synthesized with a singular structural modification to investigate structure activity relationships. Incorporation of a heteroatom was localized to the C-24 and C-25 positions. Additionally, a series of pyridine and piperidine rings were incorporated about the cholestane nucleus at the C-20 position. The positioning of the nitrogen atom was varied. The synthesis and characterization of these novel compounds serve as advances in the field of steroid research.