Design, synthesis, evaluation and structure of Allenic 1α,25-Dihydroxyvitamin D3 analogs with locked mobility at C-17
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| Title: | Design, synthesis, evaluation and structure of Allenic 1α,25-Dihydroxyvitamin D3 analogs with locked mobility at C-17 |
| Author: | Fraga Mallo, Ramón Len, Kateryna Regis, Lutzing Laverny, Gilles Loureiro, Julián Maestro Saavedra, Miguel Anxo Rochel, Natacha Rodriguez-Borges, José Enrique Mouriño Mosquera, Antonio |
| Affiliation: | Universidade de Santiago de Compostela. Departamento de Química Orgánica |
| Subject: | Allenes | Orthoester-Claisen rearrangement | Pdcatalyzed reactions | Synthesis | Vitamin D analogs | |
| Date of Issue: | 2021 |
| Publisher: | Wiley |
| Citation: | Chem. Eur. J. 2021, 27, 13384–1338. https://doi.org/10.1002/chem.202101578 |
| Abstract: | Vitamin D receptor ligands have potential for the treatment of hyperproliferative diseases and disorders related to the immune system. However, hypercalcemic effects limit their therapeutical uses and call for the development of tissue-selective new analogs. We have designed and synthesized the first examples of 1α,25-dihydroxyvitamin D3 analogs bearing an allenic unit attached to the D ring to restrict the side-chain conformational mobility. The triene system was constructed by a Pd0-mediated cyclization/Suzuki-Miyaura cross-coupling process in the presence of an allenic side chain. The allenic moiety was built through an orthoester-Claisen rearrangement of a propargylic alcohol. The biological activity and structure of (22S)-1α,25-dihydroxy-17,20-dien-24-homo-21-nor-vitamin D3 bound to binding domain of the vitamin D receptor, provide information concerning side-chain conformational requirements for biological activity |
| Publisher version: | https://doi.org/10.1002/chem.202101578 |
| URI: | http://hdl.handle.net/10347/29060 |
| DOI: | 10.1002/chem.202101578 |
| E-ISSN: | 1521-3765 |
| Rights: | © 2021 The Authors. Chemistry - A European Journal published by WileyVCH GmbH. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made |
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Except where otherwise noted, this item's license is described as © 2021 The Authors. Chemistry - A European Journal published by WileyVCH GmbH. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made