Počet záznamů: 1
Stereoselective Reduction of Steroidal 4-Ene-3-ketones in the Presence of Biomass-Derived Ionic Liquids Leading to Biologically Important 5β-Steroids
- 1.
SYSNO ASEP 0583193 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Stereoselective Reduction of Steroidal 4-Ene-3-ketones in the Presence of Biomass-Derived Ionic Liquids Leading to Biologically Important 5β-Steroids Tvůrce(i) Szánti-Pintér, Eszter (UOCHB-X) ORCID
Jirkalová, Lada (UOCHB-X)
Pohl, Radek (UOCHB-X) RID, ORCID
Bednárová, Lucie (UOCHB-X) RID, ORCID
Kudová, Eva (UOCHB-X) RID, ORCIDZdroj.dok. ACS Omega. - : American Chemical Society - ISSN 2470-1343
Roč. 9, č. 6 (2024), s. 7043-7052Poč.str. 10 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova palladium-catalyzed hydrogenation ; 3-oxo-4-ene steroids ; nanoparticles CEP LX22NPO5104 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy Způsob publikování Open access Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 001162112600001 EID SCOPUS 85184815910 DOI 10.1021/acsomega.3c08963 Anotace The stereoselective reduction of the steroidal 4-ene-3-ketone moiety (enone) affords the 5 beta-steroid backbone that is a key structural element of biologically important neuroactive steroids. Neurosteroids have been currently studied as novel and potent central nervous system drug-like compounds for the treatment of, e.g., postpartum depression. As a green methodology, we studied the palladium-catalyzed hydrogenation of steroidal 4-ene-3-ketones in the presence of ionic liquids derived from natural carboxylic acids. The hydrogenation proceeds with improved 5 beta-selectivity in the presence of tetrabutylammonium carboxylates as additives compared to the exclusive use of an organic solvent. Under optimal conditions, using tetrabutylammonium d-mandelate, the reduction of testosterone led to 5 beta-dihydrotestosterone in high yield and stereoselectivity and no byproduct formation was observed. Moreover, the catalyst could be recycled. The presence of additional substituents on the steroid backbone showed a significant effect on the 5 beta-selectivity. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Rok sběru 2025 Elektronická adresa https://doi.org/10.1021/acsomega.3c08963
Počet záznamů: 1