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Synthesis of some novel nitrogen-containing 5α-steroids based on tigogenin

Nadaraia Nanuli, Barbakadze Nana, Mulkijanyan Karen, Mshvildadze Vakhtang et Legault Jean. (2021). Synthesis of some novel nitrogen-containing 5α-steroids based on tigogenin. Bulletin of the Georgian National Academy of Sciences, 15, (3), p. 65-71.

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URL officielle: http://science.org.ge/bnas/vol-15-3.html

Résumé

A number of nitrogen-containing compounds were obtained using a condensation reaction catalyzed by acetic acid to investigate structure-chemical reactivity and structure-biological activity relationships in the search for potential biologically active steroids within ketones of the 5α-pregnane and 5α-androstane series. Novel steroidal hydrazones were synthesized from 5α-pregnan-3β-ol-20-one and 5α-pregna-9(11),16-dien-3α-ol-20-one, which, in turn, were obtained by a multistep transformation of 3β-acetoxy-5α-pregn-16-en-20-one. All of the starting steroid ketones were synthesized on the basis of a convenient domestic raw material – tigogenin, isolated from the Yucca gloriosa plant introduced in Georgia. Acetic acid catalyzed condensation reaction was carried out in ethanol using various reagents with pharmacophoric features – arylhydrazides, arylhydrazines, hydroxylamine, and semicarbazide. The structure of the newly obtained steroids was confirmed by1 H,13 C NMR, mass spectra and investigation of their biological activity is in process. The cytotoxic and antiviral activity of the previously synthesized steroid oximes, amines and hydrazones was assessed.

Type de document:Article publié dans une revue avec comité d'évaluation
Volume:15
Numéro:3
Pages:p. 65-71
Version évaluée par les pairs:Oui
Date:2021
Sujets:Sciences naturelles et génie > Sciences naturelles > Biologie et autres sciences connexes
Sciences naturelles et génie > Sciences naturelles > Chimie
Département, module, service et unité de recherche:Départements et modules > Département des sciences fondamentales
Unités de recherche > Centre de recherche sur la Boréalie (CREB)
Mots-clés:5α-steroids, antiviral activity, cytotoxic activity, epiandrosterone, hydrazine, hydrazone, pregnenolone
Déposé le:30 mai 2023 13:39
Dernière modification:30 mai 2023 13:39
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