engleski

Synthesis of New Steroid-beta-Lactam Hybrids via Palladium-Catalyzed Aminocarbonylation

The synthesis of a great number of molecular hybrids or 'chimeras' derived from steroids and other biomolecules or drugs have been reported in the literature. Steroidal beta-lactams were isolated from the plants Pachysandra terminalis and Pachysandra procumbens. The latter group of compounds showed antiestrogen-binding site inhibitory activity. There are also some reports on some steroid-beta-lactam hybrids prepared synthetically, including cholestane, androstane, estrane and cholane conjugates. Although the biological activity of most of the compounds has not been revealed, a number of 1, 2, 3-triazol-linked beta-lactam-bile acid conjugates exhibited significant antifungal and moderate antibacterial effect. In the present work, the enantiomericaly pure trans-3-amino-beta-lactams were coupled to the steroidal core via an amide bond constructed by palladium-catalyzed carbonylation reaction in order to obtain steroid-beta-lactam hybrids. Amino-beta-lactam derivatives have been used for the first time as nucleopiles in the aminocarbonylation reactions.

Steroid-beta-Lactam Hybrids; Palladium-Catalyzed Aminocarbonylation

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