(22R,23R)-3b-hydroxy-22,23-epoxy-5a-ergost-8(14)-en-15-one: Improved synthesis and toxicity to MCF-7 cells

(22R,23R)-3b-hydroxy-22,23-epoxy-5a-ergost-8(14)-en-15-one: Improved synthesis and toxicity to MCF-7 cells

The chemical synthesis of (22R,23R)-3b-hydroxy-22,23-epoxy-5a-ergost-8(14)-en-15-one from (22A)-3b-acetoxy-5a-ergosta-7,14,22-triene was improved. The stages of obtaining and isomerization of (22A)-3b-acetoxy-14a15a-epoxy-5a-ergosta-7,22-diene were optimized. The introduction of (22R,23R)-epoxide cy...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Russian journal of bioorganic chemistry 2008-11, Vol.34 (6), p.755-761
Hauptverfasser: Mehtiev, A R, Timofeev, V P, Misharin, A Yu
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The chemical synthesis of (22R,23R)-3b-hydroxy-22,23-epoxy-5a-ergost-8(14)-en-15-one from (22A)-3b-acetoxy-5a-ergosta-7,14,22-triene was improved. The stages of obtaining and isomerization of (22A)-3b-acetoxy-14a15a-epoxy-5a-ergosta-7,22-diene were optimized. The introduction of (22R,23R)-epoxide cycle was carried out by alkaline treatment of intermediate (22S,23R)-3b,23-diacetoxy-22-iodo-5a-ergost-8(14)-en-15-one. In cells of human breast carcinoma MCF-7, (22R,23R)-3b-hydroxy-22,23-epoxy-5a-ergost-8(14)-en-15-one showed a high toxicity (TC50 = 0.4±0.1 mM at 48-h incubation in serum-free medium).
ISSN:1068-1620
1608-330X
DOI:10.1134/S1068162008060174