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Synthesis of pregnane 3-carboxylic acids via Pd-catalyzed alkoxycarbonylation and their effect on NMDA receptor activity
- 1.0363595 - ÚOCHB 2012 RIV CZ eng J - Journal Article
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
R&D Projects: GA ČR(CZ) GA203/08/1498; GA ČR(CZ) GA309/07/0271
Institutional research plan: CEZ:AV0Z40550506; CEZ:AV0Z50110509
Keywords : neurosteroids * carboxylic acid * alkoxycarbonylation * steroids * NMDA receptor activity
Subject RIV: CC - Organic Chemistry
Impact factor: 1.283, year: 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.
Permanent Link: http://hdl.handle.net/11104/0199354
Number of the records: 1