MEDI 342 |
| In this work, we report a short synthesis of three new azasterols analogues 22-(piperidin-2-yl)-5a-20x-pregnan-3b-ol (1), 22-(piperidin-3-yl)-5a-20x-pregnan-3b-ol (2), 22-(piperidin-4-yl)-5a-20x-pregnan-3b-ol (3) (Scheme 1), as potential inhibitors of the (S)-adenosyl-L-methionine: D 24(25)–sterol methyl transferase (SMT) important enzyme that regulates carbon flow in the sterol pathway of plants, fungi and protozoa. Starting from 3b-hydroxipyiraniloxypregnanolone and the analogues 2, 3 and 4 trimethylsilyl-methyl pyridine, were synthesized via Peterson olefination the desired olefins favoring the formation mainly of Z-isomer. Finally the catalytic hydrogenation of the olefins and pyridin ring using Adams catalyst or Rh/Al2O3 afforded the three new desired compounds in good yield. Although their structure were elucidated by IR and NMR, the confirmation was made using GC-MS. Reference.G. Visbal, G. San-Blas, J. Murgich and H. Franco. Current Drug Targets: Infectious Disorders. 5, 211-226, 2005
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General Poster Session
7:00 PM-9:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster
Division of Medicinal Chemistry |
