Synthesis of a squalenoid oxaziridine and other new classes of squalene derivatives, as inhibitors of sterol biosynthesis

Maurizio Ceruti, Franca Viola, Gianni Balliano, Giorgio Grosa, Otto Caputo, Nicolas Gerst, Francis Schuber, Luigi Cattel

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

New classes of squalene derivatives, rationally designed as inhibitors of 2,3-oxidosqualene (SO) cyclase, a key enzyme in sterol biosynthesis, were synthesized. These were: N-methylimine 7, aminalic hydroperoxide 8, N-methyloxaziridine 9 and N-methylamide 10.9 was synthesized by a new method, in order to prevent acid decomposition of 7 and 9. The inhibitory activities of 7-10 were determined in vitro on SO cyclase associated with rat liver and yeast microsomes, and in vivo on sterol biosynthesis in 3T3 fibroblast cultures. 9 was the best inhibitor of SO cyclase associated with rat liver and yeast microsomes. In contrast, 7 and 10 strongly inhibited biosynthesis of C27-sterols in 3T3 fibroblast cultures.

Lingua originaleInglese
pagine (da-a)533-537
Numero di pagine5
RivistaEuropean Journal of Medicinal Chemistry
Volume23
Numero di pubblicazione6
DOI
Stato di pubblicazionePubblicato - 1988
Pubblicato esternamente

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