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EnglishThe synthesis of (E)- and (Z)-29-methylidyne-2,3-oxidosqualene derivatives is described starting from the C22 and C17 squalene aldehyde monobromohydrins. The conversion was achieved by means of a Wittig reaction, followed by desilylation of the terminal acetylene. For trisubstituted 1,3-enynes, preliminary alkylation with a suitable allyl bromide was performed. A new procedure for the synthesis of squalene aldehyde C27, C22 and C17 monobromohydrins is also described. Some of the new compounds behaved as inhibitors of pig liver and yeast oxidosqualene cyclase and were time-dependent inhibitors of the animal enzyme.
| Titolo: | Synthesis of (E)- and (Z)-29-methylidyne-2,3-oxidosqualene derivatives as inhibitors of liver and yeast oxidosqualene cyclase |
| Autori Riconosciuti: | |
| Autori: | Ceruti M.; Viola F.; Balliano G.; Milla P.; Roma G.; Grossi G.; Rocco F.; |
| Data di pubblicazione: | 2002 |
| Abstract: | The synthesis of (E)- and (Z)-29-methylidyne-2,3-oxidosqualene derivatives is described starting from the C22 and C17 squalene aldehyde monobromohydrins. The conversion was achieved by means of a Wittig reaction, followed by desilylation of the terminal acetylene. For trisubstituted 1,3-enynes, preliminary alkylation with a suitable allyl bromide was performed. A new procedure for the synthesis of squalene aldehyde C27, C22 and C17 monobromohydrins is also described. Some of the new compounds behaved as inhibitors of pig liver and yeast oxidosqualene cyclase and were time-dependent inhibitors of the animal enzyme. |
| Volume: | - |
| Pagina iniziale: | 1477 |
| Pagina finale: | 1486 |
| Digital Object Identifier (DOI): | 10.1039/b200888m |
| Parole Chiave: | oxidosqualene derivatives; oxidosqualene cyclase; squalene |
| Rivista: | JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. 1 |
| Appare nelle tipologie: | 03A-Articolo su Rivista |
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http://hdl.handle.net/2318/94600
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