ORGN 163 |
| A number of sterols in which heteroatoms have been substituted for carbons 24 and 25 are potent inhibitors of the &Delta 24-sterol methyl transferase (SMT) in a variety of organisms. Encouraged by those finding, we decided to synthesize a new sterol with a heterocyclic sulfurated as the side chain. In the present work, we report the synthesis of 3ß-hydroxy-23,24-bisnor-5-cholen-22-(1-N-3-methyl-imidazolil-2-thiona)(1)(Figure 1), followed by its evaluation as inhibitor of parasite growth, using Tripanosoma (Schizotrypanum) cruzi as the biological tester. The compound showed activity at µM concentrations. The detailed GC-MS analysis of the endogenous sterols of T. cruzi showed that their mode of action is associated with the inhibition of the enzyme &Delta 24(24')–sterol methyl reductase (SMR).
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Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |
