Collect. Czech. Chem. Commun. 2011, 76, 1141-1161
Published online 2011-08-31 23:18:52

Synthesis of pregnane 3-carboxylic acids via Pd-catalyzed alkoxycarbonylation and their effect on NMDA receptor activity

Eva Šťastnáa, Hana Chodounskáa,*, Vladimír Pouzara, Jiřina Borovskáb and Ladislav Vyklický, Jr.b

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
b Institute of Physiology, Academy of Sciences of the Czech Republic, v.v.i., Vídeňská 1083, 142 20 Prague 4, Czech Republic


We have prepared 20-oxo-5α- and 20-oxo-5β-pregnane-3-carboxylic acids by palladium catalyzed alkoxycarbonylation using triflate and nonaflate as the leaving groups in this substitution reaction. The activity of the synthesized compounds was studied in cultured rat hippocampal neurons under voltage-clamp conditions. The 5β-carboxylic acid derivatives were found to diminish NMDA-induced responses, whereas the 5α-derivative potentiated the response.

Keywords: Neurosteroids; Carboxylic acid; Alkoxycarbonylation; NMDA receptor activity; Steroids.

References: 24 live references.