New 1α,25-dihydroxy-19-norvitamin D3 analogs with a frozen A-ring conformation

Glebocka, Agnieszka; Siciński, Rafał R.; Plum, Lori A.; DeLuca, Hector F.

doi:10.1016/j.jsbmb.2010.03.011

Cited by 7 publications

(4 citation statements)

References 19 publications

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“…Figure 19 (2009-2010) [271][272][273][274][275][276][277][278][279][280][281][282][283]. Intensive research activity was carried out on Gemini compounds 1053-1069 [273].…”

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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“…Figure 19 (2009-2010) [271][272][273][274][275][276][277][278][279][280][281][282][283]. Intensive research activity was carried out on Gemini compounds 1053-1069 [273].…”

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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“…Okamura first suggested that the 1a-hydroxyl must be in the equatorial position when interacting with the VDR [32]. This idea has been confirmed with the synthesis of analogs where the 1a-hydroxyl is apparently restricted to the axial configuration [33,34].…”

Section: )mentioning

confidence: 91%

Alterations in 1,25-Dihydroxyvitamin D3 Structure that Produce Profound Changes in in Vivo Activity

DeLuca

Plum

2011

Vitamin D

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“…Unexpectedly, these compounds exhibited a calcemic response, probably due to their metabolic conversion in living organisms. To verify this hypothesis, DeLuca and co-workers [29] focused their attention on preparing analogs in which the additional ring possessed only carbon units (55 and 56). To obtain the latter compounds, a similar procedure to that above was followed with Grundmann's ketone 54 and the A-ring synthon 53 that comes from (−)-quinic acid in a multi-step synthesis.…”

Section: Synthesis Of A-ring-modified 1α25-(oh) 2 -19-nor-vitamin Dmentioning

confidence: 99%

Strategies for the Synthesis of 19-nor-Vitamin D Analogs

Fernández

Ferrero

2020

Pharmaceuticals

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1α,25-Dihydroxyvitamin D3 [1α,25-(OH)2-D3], the hormonally active form of vitamin D3, classically regulates bone formation, calcium, and phosphate homeostasis. In addition, this hormone also exerts non-classical effects in a wide variety of target tissues and cell types, such as inhibition of the proliferation and stimulation of the differentiation of normal and malignant cells. However, to produce these actions, supraphysiological doses are required resulting in calcemic effects that limit the use of this natural hormone. During the past 30 years, many structurally modified analogs of the 1α,25-(OH)2-D3 have been synthesized in order to find derivatives that can dissociate the beneficial antiproliferative effects from undesired calcemic effects. Among these candidates, 1α,25-(OH)2-19-nor-D3 analogs have shown promise as good derivatives since they show equal or better activity relative to the parent hormone but with reduced calcemic effects. In this review, we describe the synthetic strategies to obtain the 19-nor-D3 derivatives and briefly describe their physiological activities.

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New 1α,25-dihydroxy-19-norvitamin D3 analogs with a frozen A-ring conformation

Cited by 7 publications

References 19 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

Alterations in 1,25-Dihydroxyvitamin D3 Structure that Produce Profound Changes in in Vivo Activity

Strategies for the Synthesis of 19-nor-Vitamin D Analogs

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