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Dostęp zamkniętyD-seco-Vitamin D analogs having reversed configurations at C-13 and C-14: Synthesis, docking studies and biological evaluation.
| dc.abstract.en | Prompted by results of molecular modeling performed on the seco-d-ring-vitamins D, we turned our attention to such analogs, having reversed configurations at C-13 and C-14, as the next goals of our studies on the structure-activity relationship for vitamin D compounds. First, we developed an efficient total synthesis of the “upper” C/seco-d-ring fragment with a 7-carbon side chain. Then, we coupled it with A-ring fragments using Sonogashira or Wittig-Horner protocol, providing the targeted D-seco analogs of 1α,25-dihydroxyvitamin D3 and 1α,25-dihydroxy-19-norvitamin D3 possessing a vinyl substituent at C-14 and a double bond between C-17 and C-20.The affinities of the synthesized vitamin D analogs to the full-length recombinant rat VDR were examined, as well as their differentiating and transcriptional activities. In these in vitro tests, they were significantly less active compared to 1α,25-(OH)2D3. Moreover, it was established that the analogs tested in vivo in rats showed no calcemic potency. |
| dc.affiliation | Uniwersytet Warszawski |
| dc.contributor.author | DeLuca, Hector F. |
| dc.contributor.author | Plum, Lori A. |
| dc.contributor.author | Siciński, Rafał |
| dc.contributor.author | Szybiński, Marcin |
| dc.contributor.author | Sokołowska, Katarzyna |
| dc.date.accessioned | 2024-01-24T22:14:13Z |
| dc.date.available | 2024-01-24T22:14:13Z |
| dc.date.issued | 2017 |
| dc.description.finance | Nie dotyczy |
| dc.description.volume | 173 |
| dc.identifier.doi | 10.1016/J.JSBMB.2016.08.009 |
| dc.identifier.issn | 0960-0760 |
| dc.identifier.uri | https://repozytorium.uw.edu.pl//handle/item/105382 |
| dc.language | eng |
| dc.pbn.affiliation | chemical sciences |
| dc.relation.ispartof | Journal of Steroid Biochemistry and Molecular Biology |
| dc.relation.pages | 57-63 |
| dc.rights | ClosedAccess |
| dc.sciencecloud | nosend |
| dc.subject.en | Secosteroids |
| dc.subject.en | Vitamin D analogs |
| dc.subject.en | 2MD |
| dc.subject.en | Vitamin D receptor |
| dc.subject.en | Sonogashira coupling |
| dc.title | D-seco-Vitamin D analogs having reversed configurations at C-13 and C-14: Synthesis, docking studies and biological evaluation. |
| dc.type | JournalArticle |
| dspace.entity.type | Publication |