2′-Aminoanalogues of the cruciferous phytoalexins spirobrassinin, 1-methoxyspirobrassinin and 1-methoxyspirobrassinol methyl ether: Synthesis and anticancer properties

Budovská, Mariana; Tischlerová, Viera; Mojžiš, Ján; Harvanová, Marianna; Kozlov, Oleksandr; Gondová, Taťána; Tomášková, Nataša

doi:10.1016/j.tet.2017.09.033

Cited by 14 publications

(3 citation statements)

References 23 publications

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“…Some years later, SIDA phenomenon was also detected for a nonracemic solution of a 2 -amino analog of spirobrassinin 69 (Figure 9) in 1 H and 13 C NMR spectra recorded in a C 6 D 6 solution [59].…”

Section: Natural Productsmentioning

confidence: 88%

“…Based on the chemical shift variation measured for the split signals of one of the protons in α-position with respect to the imide nitrogen (Figure 9), the authors inferred a preference for the formation of homochiral dimers in a C6D6 solution. Some years later, SIDA phenomenon was also detected for a nonracemic solution of a 2′-amino analog of spirobrassinin 69 (Figure 9) in 1 H and 13 C NMR spectra recorded in a C6D6 solution [59].…”

Section: Natural Productsmentioning

confidence: 88%

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The Phenomenon of Self-Induced Diastereomeric Anisochrony and Its Implications in NMR Spectroscopy

Aiello,

Uccello Barretta,

Balzano

et al. 2023

Molecules

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Nuclear magnetic resonance (NMR) spectroscopy is an analytical technique largely applied in the analysis of discrimination processes involving enantiomeric substrates and chiral agents, which can interact with the analyte either via covalent bonding or via formation of diastereomeric solvates. However, enantiodiscrimination has been observed, in some cases, even in the absence of any additional chiral selector. The reasons behind this phenomenon must be found in the capability of some chiral substrates to interact with themselves by forming diastereomeric solvates in solution that can generate nonequivalences in the NMR spectra of enantiomerically enriched mixtures. As a result, differentiation of enantiomers is observed, thus allowing the quantification of the enantiomeric composition of the mixture under investigation. The tendency of certain substrates to self-aggregate and to generate diastereomeric adducts in solution can be defined as Self-Induced Diastereomeric Anisochrony (SIDA), but other acronyms have been used to refer to this phenomenon. In the present work, an overview of SIDA processes investigated via NMR spectroscopy will be provided, with a particular emphasis on the nature of the substrates involved, on the interaction mechanisms at the basis of the phenomenon, and on theoretical treatments proposed in the literature to explain them.

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Section: Natural Productsmentioning

confidence: 88%

Section: Natural Productsmentioning

confidence: 88%

The Phenomenon of Self-Induced Diastereomeric Anisochrony and Its Implications in NMR Spectroscopy

Aiello,

Uccello Barretta,

Balzano

et al. 2023

Molecules

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“…Homobrassinin (Type II) is more active than brassinin (1) and has been shown to cause ROS dependent apoptosis in Caco-2 colorectal cancer cells [28]. Likewise, the introduction of a substituted phenyl amino group to the compounds 3 and 4 (Type V) resulted in enhanced antiproliferative effect against human cancer cell lines [27,29]. Structural modification of phytoalexin (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether [(2R,3R)-(-)-6a] -synthetic 2-aminoanalogues (Type VII), 2'-aminoanalogues (Type VIII) or 2,2'diaminoanalogues (Type IX) exhibited remarkable anticancer activity [25,26,[29][30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and biological evaluation of novel 5-bromo derivatives of indole phytoalexins

Budovská

Selešová

Tischlerová

et al. 2020

Preprint

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The increasing diversity of small molecule libraries is a major source for the discovery of new drug candidates. In term of this trend, we report the synthesis five series 5-bromosubstituted derivatives of indole phytoalexins Type A-E using straightforward synthetic approach. Novel compounds were screened in vitro for antiproliferative/cytotoxic activity against seven human cancer cell lines by MTT assay. Evaluation of their antiproliferative potency showed that the activity of some analogues was better or comparable to that of cisplatin and at the same time the toxicity of these compounds on 3T3 cells was lower than that of cisplatin. We found that all 5-bromosubstituted analogues of indole phytoalexins Type A-E exhibited lower or approximately the same activities as a previously studied corrensponding non-brominated compounds.

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The Self‐Disproportionation of Enantiomers ( SDE ): Fluorine as an SDE ‐Phoric Substituent

Han¹,

Fustero²,

Moriwaki³

et al. 2021

Organofluorine Chemistry

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2′-Aminoanalogues of the cruciferous phytoalexins spirobrassinin, 1-methoxyspirobrassinin and 1-methoxyspirobrassinol methyl ether: Synthesis and anticancer properties

Cited by 14 publications

References 23 publications

The Phenomenon of Self-Induced Diastereomeric Anisochrony and Its Implications in NMR Spectroscopy

The Phenomenon of Self-Induced Diastereomeric Anisochrony and Its Implications in NMR Spectroscopy

Design, synthesis and biological evaluation of novel 5-bromo derivatives of indole phytoalexins

The Self‐Disproportionation of Enantiomers ( SDE ): Fluorine as an SDE ‐Phoric Substituent

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