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

0363595 - ÚOCHB 2012 RIV CZ eng J - Článek v odborném periodiku
Šťastná, Eva - Chodounská, Hana - Pouzar, Vladimír - Borovská, Jiřina - Vyklický ml., Ladislav
Synthesis of pregnane 3-carboxylic acids via Pd-catalyzed alkoxycarbonylation and their effect on NMDA receptor activity.
Collection of Czechoslovak Chemical Communications. Roč. 76, č. 9 (2011), s. 1141-1161. ISSN 0010-0765
Grant CEP: GA ČR(CZ) GA203/08/1498; GA ČR(CZ) GA309/07/0271
Výzkumný záměr: CEZ:AV0Z40550506; CEZ:AV0Z50110509
Klíčová slova: neurosteroids * carboxylic acid * alkoxycarbonylation * steroids * NMDA receptor activity
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 1.283, rok: 2011

We have prepared 20-oxo-5alpha- and 20-oxo-5beta-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 5beta-carboxylic acid derivatives were found to diminish NMDA-induced responses, whereas the 5alpha-derivative potentiated the response.
Trvalý link: http://hdl.handle.net/11104/0199354