| Literature DB >> 23811018 |
Anita Pietraszek1, Maura Malińska, Michał Chodyński, Małgorzata Krupa, Krzysztof Krajewski, Piotr Cmoch, Krzysztof Woźniak, Andrzej Kutner.
Abstract
The hybrid analogs of 1,25-dihydroxyergocalciferol (PRI-5201 and PRI-5202) were synthesized as potential anticancer agents using a convergent strategy. The analogs were designed by combining a 19-nor modification of the A-ring with the homologated and rigidified ergocalciferol-like side-chain of the previously obtained analogs PRI-1906 and PRI-1907. The strategy also allowed the novel efficient synthesis of 19-nor-1,25-dihydroxyergocalciferol (paricalcitol, PRI-5100) and its (24R)-diastereomer (PRI-5101). The single crystal X-ray structures of the 19-nor analogs (PRI-5100 and PRI-5101) were solved and refined. The A-ring of both analogs adopts exclusively chair β-conformation in the solid state. The side-chain of these analogs is coplanar with the CD-ring plane, while it is perpendicular in 1,25-dihydroxycholecalciferol. CrownEntities:
Keywords: 19-nor vitamin D analogs; A-ring synthon; CD-ring fragment; Convergent synthesis; Paricalcitol; Single crystal X-ray structure
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Year: 2013 PMID： 23811018 DOI： 10.1016/j.steroids.2013.06.001
Source DB: PubMed Journal: Steroids ISSN： 0039-128X Impact factor: 2.668