Synthesis of 19-norcalcitriol analogs with elongated side chain

Brzeminski, Pawel; Fabisiak, Adrian; Sektas, Katarzyna; Berkowska, Klaudia; Marcinkowska, Ewa; Siciński, Rafał R.

doi:10.1016/j.jsbmb.2017.08.008

Cited by 3 publications

(2 citation statements)

References 17 publications

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“…Figure 28 (2018-2019) [365][366][367][368][369][370][371][372][373][374][375][376][377][378]. 21-nor-17(S)-Methyl-20(22),23(24)-didehydro-26,26, 26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D 3 (1600) [368] bound strongly to VDR ligand binding domain and induced VDR transcriptional activity.…”

Section: Resultsmentioning

confidence: 99%

The Centennial Collection of VDR Ligands: Metabolites, Analogs, Hybrids and Non-Secosteroidal Ligands

Maestro

Seoane

2022

Nutrients

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Section: Resultsmentioning

confidence: 99%

The Centennial Collection of VDR Ligands: Metabolites, Analogs, Hybrids and Non-Secosteroidal Ligands

Maestro

Seoane

2022

Nutrients

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“…Structural fragments 1 and 2 represent modified side chains precursors. This part of vitamins D is often chemically modified and, owing to the flexibility of this side chain, it significantly influences the binding affinity of the analogues with VDR [30]. For instance, replacing either the C26-and C27-methyl groups with ethyl moieties resulted in the superagonist, KH1060, which binds to VDR with high affinity as well as decreased calcemic side effects [28].…”

Section: Introductionmentioning

confidence: 99%

Relation between Crystal Structures of Precursors and Final Products: Example of Vitamin D Intermediates

et al. 2020

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In this paper, we proved that the solid-state structure of vitamin D analog is well represented by the structures of its structural fragments. This is important in predicting the biological activity of vitamin D analogs that are not available in the solid form. The previously published crystal structure of advanced vitamin D intermediate provided additional insights into vitamin D properties. A similar analysis based on simple vitamin D intermediate analogues showed that precursors crystallized in the space groups typical for vitamins D; geometrical parameters were related to the corresponding parameters in the vitamin D analogues; and crystal structures of the basic intermediates and their final products contained similar intermolecular interactions, essential for the infinite hydrogen bond motif observed in the vitamin D analogues. The energy of these interactions is related as shown by theoretical calculations, that is, energy frameworks analysis. Moreover, analysis of the hydrogen bonds motifs revealed a relation between these motifs and the absolute configuration of basic intermediates as well as the space orientation of the exocyclic methylene group in the final structures.

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Synthesis of Gemini analogs of 19-norcalcitriol and their platinum(II) complexes

Brzeminski

Fabisiak

Berkowska

et al. 2020

Bioorganic Chemistry

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Synthesis of 19-norcalcitriol analogs with elongated side chain

Cited by 3 publications

References 17 publications

The Centennial Collection of VDR Ligands: Metabolites, Analogs, Hybrids and Non-Secosteroidal Ligands

The Centennial Collection of VDR Ligands: Metabolites, Analogs, Hybrids and Non-Secosteroidal Ligands

Relation between Crystal Structures of Precursors and Final Products: Example of Vitamin D Intermediates

Synthesis of Gemini analogs of 19-norcalcitriol and their platinum(II) complexes

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