Retiferols – synthesis and biological activity of a conceptually novel class of vitamin D analogs

Bolla, Narasimha Rao; Marcinkowska, Ewa; Brown, Geoffrey; Kutner, Andrzej

doi:10.1517/13543776.2014.898061

Cited by 7 publications

(7 citation statements)

References 43 publications

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“…This is due to the indirect formation of hydrogen bonds between the hydroxyls of the A-ring involving water molecules [ 32 ]. The CD ring system is derived from a steroid precursor and its presence is not crucial for the vitamin D compound to show biological activity [ 33 , 34 , 35 ].…”

Section: Structure Of Active Forms Of Vitamin Dmentioning

confidence: 99%

Structure and the Anticancer Activity of Vitamin D Receptor Agonists

Powała,

Żołek,

Brown

et al. 2024

IJMS

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Vitamin D is a group of seco-steroidal fat-soluble compounds. The two basic forms, vitamin D2 (ergocalciferol) and vitamin D3 (cholecalciferol), do not have biological activity. They are converted in the body by a two-step enzymatic hydroxylation into biologically active forms, 1α,25-dihydroxyvitamin D2 [ercalcitriol, 1,25(OH)2D2] and 1α,25-dihydroxyvitamin D3 [calcitriol, 1,25(OH)2D3], which act as classical steroid hormones. 1,25(OH)2D3 exerts most of its physiological functions by binding to the nuclear vitamin D receptor (VDR), which is present in most body tissues to provide support to a broad range of physiological processes. Vitamin D-liganded VDR controls the expression of many genes. High levels of 1,25(OH)2D3 cause an increase in calcium in the blood, which can lead to harmful hypercalcemia. Several analogs of 1,25(OH)2D3 and 1,25(OH)2D2 have been designed and synthesized with the aim of developing compounds that have a specific therapeutic function, for example, with potent anticancer activity and a reduced toxic calcemic effect. Particular structural modifications to vitamin D analogs have led to increased anticancer activity and reduced calcemic action with the prospect of extending work to provide future innovative therapies.

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Section: Structure Of Active Forms Of Vitamin Dmentioning

confidence: 99%

Structure and the Anticancer Activity of Vitamin D Receptor Agonists

Powała,

Żołek,

Brown

et al. 2024

IJMS

Self Cite

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“…This method was efficiently employed for the synthesis of the hormone 1,25D 3 and its analogs including retiferols of type 64 (Scheme 10). [85][86][87] Sato's synthesis of 1,25D 3 uses enyne 60, which was converted via titanium intermediate 61 to alcohol 62. Protection, bromide elimination and desilylation afforded diene 22, which was coupled to boronate 23b in the presence of catalytic PdCl 2 (dppf) and KOH in aqueous-THF to give, after deprotection, the natural hormone 1,25D 3 in 82% yield.…”

Section: The Pd(0)-catalyzed Cross Coupling Approach (H)mentioning

confidence: 99%

Pd(0)‐Catalyzed‐Mediated Synthesis of Vitamin D Compounds

Mouriño

2023

Adv Synth Catal

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Abstract1α,25‐Dihydroxyvitamin D3 (1,25D3), the hormonally active form of vitamin D3, regulates mineral homeostasis, cell growth, cell differentiation‐proliferation, apoptosis, and immune responses. 1,25D3 activates more than 229 genes associated with several diseases, including arthritis, diabetes and cancer, suggesting its implications in a broader range of biological functions than originally thought. Despite the wide range of biological activities, the clinical applications of 1,25D3 have been limited due to its collateral hypercalcemic effects. This problem has boosted intense synthetic activity in the vitamin D area in the last decades aimed at the development of highly active and non‐calcemic analogs for treatment of hyperproliferative diseases. This review covers the most useful synthetic approaches to 1,25D3 analogs containing the natural vitamin D triene system with emphasis on the Pd(0)‐catalyzed transformations involved in the formation of the vitamin D triene system and A‐ring synthons.

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“…Another interesting concept is to make a hybrid vitamin D analogue that combines vitamin D functions with some complementary action. Retiferols combining vitamin D and retinoid functions have been successfully created by the Kutner group could have some utility of the treatment of bone disease, while the VDR agonist has also been combined with a histone deacetylase inhibitor in the form of DK‐406 (Table ) by Gleason and colleagues , its value arising from the fact that both agents are regulators of gene transcription and might be expected to act synergistically on certain vitamin D‐dependent genes.…”

Section: Antagonists Nonsteroidal Scaffolds and Hybrid Vitamin D Molmentioning

confidence: 99%

Update on pharmacologically‐relevant vitamin D analogues

Jones

Kaufmann

2018

Brit J Clinical Pharma

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Pharmacologists have been interested in vitamin D since its metabolism was elucidated in the early 1970s. Despite the synthesis of thousands of vitamin D analogues in the hope of separating its calcemic and anti-proliferative properties, few molecules have reached the market for use in the treatment of clinical conditions from psoriasis to chronic kidney disease. This review discusses vitamin D drugs, recently developed or still under development, for use in various diseases, but in particular bone disease. In the process we explore the mechanisms postulated to explain the action of these vitamin D analogues including action through the vitamin D receptor, action through other receptors e.g. FAM57B2 and dual action on transcriptional processes.

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Retiferols – synthesis and biological activity of a conceptually novel class of vitamin D analogs

Cited by 7 publications

References 43 publications

Structure and the Anticancer Activity of Vitamin D Receptor Agonists

Structure and the Anticancer Activity of Vitamin D Receptor Agonists

Pd(0)‐Catalyzed‐Mediated Synthesis of Vitamin D Compounds

Update on pharmacologically‐relevant vitamin D analogues

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