Convergent Approaches and Biological Activity of C1 and/or C3 Mono or Diamino Derivatives of 1α, 25‐Dihydroxy‐19‐nor‐vitamin D3. Key Enzymatic Desymmetrization of A‐Ring Synthon Precursor. Issue 2 (18th January 2023)

• Record Type: Journal Article
• Authors: González‐García, Tania; Verstuyf, Annemieke; Verlinden, Lieve; Fernández, Susana; Ferrero, Miguel
• Is Part Of: Advanced synthesis & catalysis. Volume 365:Issue 2(2023)
• Page Start: 201
• Page End: 210
• Publication Date: 2023-01-18
• Subjects: 19-nor-vitamin D3 analogs -- biocatalysis -- enzymatic desymmetrization -- A-ring amino derivatives of calcitriol; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202201158
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Three novel 19‐ nor ‐1α, 25‐dihydroxyvitamin D3 derivatives modified at C1 and/or C3 with an amino group were synthesized to study the influence of the substitution of one or both hydroxyl groups of A‐ring by amino groups on the affinity for vitamin D receptor (VDR) and vitamin D binding protein (hDBP), and also on the antiproliferative activity. The A‐ring precursors were prepared from cis, cis ‐1, 3, 5‐cyclohexanetriol applying a desymmetrization reaction of a prochiral 1, 3‐diol catalyzed by Pseudomonas cepacia lipase as a key step. The structural elucidation of diastereoisomers were unambiguously assigned by NMR spectroscopy. Abstract :