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Synthesis of New 5α-Steroidal Hydrazones from Tigogenin

Nadaraia Nanuli, Barbakadze Nana, Kakhabrishvili Meri, Mulkijanyan Karen, Mshvildadze Vakhtang et Legault Jean. (2022). Synthesis of New 5α-Steroidal Hydrazones from Tigogenin. Bulletin of the Georgian National Academy of Sciences, 16, (2), p. 129-134.

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In the present study potentially biologically active steroids, new hydrazones, semicarbazones, and 20O-methyloxime have been synthesized from ketones of the 5α-pregnene, 5α-pregnane, and 5αandrostane series. The condensation reaction of ketones – 5α-pregn-16-en-3β-ol-20-one, 5α-pregnan3β-ol-20-one and 5α-androstan-3β-ol-17-one – with various arylhydrazides, semicarbazide, and methoxyamine was carried out in ethanol with a catalytic amount of acetic acid. The starting ketones were made from tigogenin, an aglycone of steroidal saponins that is a domestic raw material for the synthesis of 5α-series steroids. Tigogenin was isolated from the Yucca gloriosa plant, which was introduced in Georgia.1H,13C NMR and mass spectra were used to confirm the structure of the newly obtained steroids. The cytotoxicity of these and previously synthesized hydrazones was investigated in vitro using the Rezazurin reduction test and Hoechst test aginst lung carcinoma (A549), colorectal adenocarcinoma (DLD-1) and normal skin fibroblasts (WS-1) cell lines in comparison to etoposide. The results show that, of all the compounds studied, only p-methyl-and pmethoxybenzoylhydrazone 5α-pregnan-3β-ol-20-one are of particular interest since, unlike the others, they demonstrate activity comparable to etoposide.

Type de document:Article publié dans une revue avec comité d'évaluation
Pages:p. 129-134
Version évaluée par les pairs:Oui
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:Unités de recherche > Centre de recherche sur la Boréalie (CREB)
Départements et modules > Département des sciences fondamentales
Mots-clés:5α-steroids, cytotoxic activity, epiandrosterone, hydrazide, hydrazone, oxime, pregnanolone, pregnenolone
Déposé le:30 mai 2023 13:52
Dernière modification:30 mai 2023 13:52
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