Calcitriol derivatives with two different side chains at C-20

Maehr, Hubert; Uskoković, Milan R.; Reddy, G. Satyanarayana; Adorini, Luciano

doi:10.1016/j.jsbmb.2004.03.047

Cited by 7 publications

(2 citation statements)

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“…Calcitriol analogues with two different side chains at C (20) have been synthesized 121 and their use as probes of the vitamin D receptor has been explored. 122 The crystal structure of the vitamin D nuclear receptor liganded with the vitamin D side chain analogue calcipotriol 45, has been determined 123 in order to provide an insight into the biological activity of these analogues.…”

Section: Cholestanesmentioning

confidence: 99%

Steroids: partial synthesis in medicinal chemistry

Hanson

2006

Nat. Prod. Rep.

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Section: Cholestanesmentioning

confidence: 99%

Steroids: partial synthesis in medicinal chemistry

Hanson

2006

Nat. Prod. Rep.

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“…We also considered their biological activities which are studied in the literature [3]. Recently, we reported the synthesis of a new vitamin D2 analogue and the evaluation of its biological activity on colon cancer [4]. In the continuation of our work on the analogues of vitamin D, we synthesized two new molecules of calcitriol from an oxolane ring and its side chains [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and X-ray crystallography of (1R,3aR,7aR)-1-((S)-1-((2R,5S)-5-(3-hydroxypentan-3-yl)tetrahydrofuran-2-yl)ethyl)-7a-methyloctahydro-4H-inden-4-one

et al. 2017

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Recent Developments of 19‐Nor‐1,25‐dihydroxyvitamin D₃ Analogues

2013

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The vitamin D hormone, 1α,25-dihydroxyvitamin D3 [1,25-(OH)2 D3 ], exerts its hormonal effects predominantly on intestine, bone, and kidney, where it plays a crucial role in calcium and phosphorus homeostasis and bone mineralization. In addition to its classical actions, 1,25(OH)2 D3 exerts pleiotropic effects in a wide variety of target tissues and cell types, often in an autocrine/paracrine fashion. These biological activities of 1,25(OH)2 D3 have suggested a multitude of potential therapeutic applications for the vitamin D hormone in the treatment of hyperproliferative disorders (e.g. cancer and psoriasis), immune dysfunction (autoimmune diseases), and endocrine disorders (e.g. hyperparathyroidism). However, the calcemic effects induced by 1,25(OH)2 D3--hypercalcemia, increased bone resorption, and soft tissue calcification--limit the use of the natural ligand in these clinical applications. Therefore, numerous 1,25(OH)2 D3 analogues have been synthesized with the intent of producing therapeutic agents devoid of hypercalcemic and hyperphosphatemic side effects. To this aim, much attention has been focused on the development of 19-nor-vitamin D3 derivatives that lack the ring-A exocyclic methylene group (C19). In this review, the 19-nor-1,25(OH)2 D3 analogues are classified according to modifications made at the A-ring, the side chain, or both the A-ring and side chain, as well as other positions. The biological activities of these 19-nor-1,25(OH)2 D3 analogues are summarized and their structure-activity relationships and binding features with the vitamin D receptor (VDR) are discussed.

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Calcitriol derivatives with two different side chains at C-20

Cited by 7 publications

References 11 publications

Steroids: partial synthesis in medicinal chemistry

Steroids: partial synthesis in medicinal chemistry

Synthesis and X-ray crystallography of (1R,3aR,7aR)-1-((S)-1-((2R,5S)-5-(3-hydroxypentan-3-yl)tetrahydrofuran-2-yl)ethyl)-7a-methyloctahydro-4H-inden-4-one

Recent Developments of 19‐Nor‐1,25‐dihydroxyvitamin D₃ Analogues

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Calcitriol derivatives with two different side chains at C-20

Cited by 7 publications

References 11 publications

Steroids: partial synthesis in medicinal chemistry

Steroids: partial synthesis in medicinal chemistry

Synthesis and X-ray crystallography of (1R,3aR,7aR)-1-((S)-1-((2R,5S)-5-(3-hydroxypentan-3-yl)tetrahydrofuran-2-yl)ethyl)-7a-methyloctahydro-4H-inden-4-one

Recent Developments of 19‐Nor‐1,25‐dihydroxyvitamin D3 Analogues

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Recent Developments of 19‐Nor‐1,25‐dihydroxyvitamin D₃ Analogues