Stable nitrones from 17β-hydroxylamine derivatives of 8β- and 8α-estrone

Kaspar, Peter; Witzel, Herbert

doi:10.1016/s0039-128x(83)90036-3

Cited by 2 publications

(1 citation statement)

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“…The stereochemical structure of 8 and 9 (EtOAc) was ultimately confirmed though a single crystal X-ray diffraction experiment by using Cu Kα radiation, and the absolute configuration as 20R (compound 8), 20S (compound 9), respectively (Cambridge Crystallographic Data Centre 2010171, 2010608; Figure 2). The same reaction sequence was applied to get MeON-dehydroepiandrosterone 12 and MeON-estrone 15 [25] as glycosyl acceptors are illustrated in Schemes 3 and 4. The synthesis of steroidal MeON-neoglycosides was conducted by the neoglycosylation reaction method.…”

Section: Chemistrymentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of Steroidal Glycoconjugates as Potential Antiproliferative Agents

et al. 2021

ChemMedChem

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To systematically evaluate the impact of neoglycosylation upon the anticancer activities and selectivity of steroids, four series of neoglycosides of diosgenin, pregnenolone, dehydroepiandrosterone and estrone were designed and synthesized according to the neoglycosylation approach. The structures of all the products were elucidated by NMR analysis, and the stereochemistry of C20‐MeON‐pregnenolone was confirmed by crystal X‐ray diffraction. The compounds′ cytotoxicity on five human cancer cell lines was evaluated using a Cell Counting Kit‐8 assay, and structure–activity relationships (SAR) are discussed. 2‐deoxy‐d‐glucoside 5 k displayed the most potent antiproliferative activities against HepG2 cells with an IC50 value of 1.5 μM. Further pharmacological experiments on compound 5 k on HepG2 cells revealed that it could cause morphological changes and cell‐cycle arrest at the G0/G1 phase and then induced the apoptosis, which might be associated with the enhanced expression of high‐mobility group Box 1 (HMGB1). Taken together, these findings prove that the neoglycosylation of steroids could be a promising strategy for the discovery of potential antiproliferative agents.

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Section: Chemistrymentioning

confidence: 99%