Synthesis of sphingomyelin carbon analogues as sphingomyelinase inhibitors |
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Authors: | Hakogi Toshikazu Monden Yoshiko Taichi Misako Iwama Seiji Fujii Shinobu Ikeda Kiyoshi Katsumura Shigeo |
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Institution: | School of Science, Kwansei Gakuin University, Gakuen, Sanda, Hyogo 669-1337, Japan. |
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Abstract: | The highly efficient and stereocontrolled syntheses of sphingomyelin carbon analogues 1 and 2 were achieved by effectively utilizing Hofmann rearrangement of enantiomerically pure beta-hydroxyamide 7, which was prepared by an asymmetric hydrogenation of alpha-acyl-gamma-butyrolactone 9 and ring opening with NH(3). Intermediary isocyanate 6 was selectively trapped with the vicinal hydroxy group in an intramolecular fashion to produce an oxazolidinone derivative, 5. In the synthesis of a quite polar compound such as 1, a convenient one-pot procedure of the introduction of a benzyloxycarbonyl group into the hydroxy group resulting from the oxazolidinone ring opening is another key point, because, in addition to the efficiency, this protecting group was easily removable by a simple procedure and workup at the final step. Both synthesized compounds 1 and 2 showed moderate inhibitory activity toward sphingomyelinase from B. cereus. |
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