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Allopregnanolone (3α-Hydroxy-5α-pregnan-20-one) Derivatives with a Polar Chain in position 16α: Synthesis and activity
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SYSNO ASEP 0323744 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Allopregnanolone (3α-Hydroxy-5α-pregnan-20-one) Derivatives with a Polar Chain in position 16α: Synthesis and activity Title Deriváty allopregnanolonu (3α-hydroxy-5α-pregnan-20-one) s polárním řetězcem v poloze 16α: Syntéza and aktivita Author(s) Slavíková, Barbora (UOCHB-X) RID, ORCID
Krištofíková, Z. (CZ)
Chodounská, Hana (UOCHB-X) RID, ORCID
Buděšínský, Miloš (UOCHB-X) RID, ORCID
Durán, F. J. (AR)
Veleiro, A. S. (AR)
Burton, G. (AR)
Kasal, Alexander (UOCHB-X)Number of authors 8 Source Title Journal of Medicinal Chemistry. - : American Chemical Society - ISSN 0022-2623
Roč. 52, č. 7 (2009), s. 2119-2125Number of pages 7 s. Language eng - English Country US - United States Keywords Michael addition ; carbamates ; [35S]TBPS Subject RIV CC - Organic Chemistry R&D Projects GA203/06/1605 GA ČR - Czech Science Foundation (CSF) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000264835800033 DOI 10.1021/jm801454a Annotation The lipophilic nature of allopregnanolone prevents its user-friendly application in human medicine. New allopregnanolone analogues with polar groups introduced into position 16α were prepared and tested. The Michael addition to derivatives of pregn-16-en-20-one was the key reaction step. The link between the steroid skeleton and the new side chain was either a methylene group (when diethyl malonate was added) or an oxygen atom (when a hydroxy derivative was added). [35S]TBPS displacement was used to evaluate the products. Several carbamates (but not their parent alcohols) displaced TBPS from the picrotoxin binding site on GABAA receptors. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2009
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