Acetylenic Inhibitors of C-22 Hydroxylase of Ecdysone Biosynthesis

Article abstract of DOI:10.1006/bioo.1994.1003

Acetylenic derivatives of cholesterol designed to be inhibitors of ecdysteroid biosynthesis were prepared.The side chains of these compounds differ additionally from that of cholesterol by stereochemical modifications at C-17 and C-20.A bicyclic acetylenic compound containing the partial structure of the C and D rings of the cholesterol nucleus was also synthesized.These compounds were devised with the aim of inhibiting the C-22 hydroxylation of ecdysone biosynthesis by a suicide substrate mechanism.One of these molecules inhibits very efficiently the synthesis of ecdysone in prothoracic glands in vitro.