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- W2023447551 abstract "Vitamin D compounds possessing A rings prohibited from flipping to the alternative chair form (i.e., analogues 2 and 26) were synthesized. The bicyclic fragment 22 consisting of the fused cyclohexane and dihydropyran rings was constructed via the ring-closing metathesis route. Also, a homologous synthon 23 with an attached dihydropyran ring was successfully synthesized using this strategy. The carbonyl deprotection in 22 yielded cyclohexanone 5 that was subjected to Julia coupling with the anion of the phenylthiazoline sulfone 25. In the resulting isomeric 19-norvitamins 2 and 26, their A rings can exist only in the α- and β-conformation. The analogue 26 was 300 times more active in binding to the vitamin D receptor protein, 30 times more effective in causing HL-60 differentiation, and 10 times more active in transcription. These results confirm that the β-chair form of the vitamin D ring A is necessary for the binding to the receptor." @default.
- W2023447551 created "2016-06-24" @default.
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- W2023447551 date "2009-04-29" @default.
- W2023447551 modified "2023-10-09" @default.
- W2023447551 title "New 1α,25-Dihydroxy-19-norvitamin D<sub>3</sub> Compounds Constrained in a Single A-Ring Conformation: Synthesis of the Analogues by Ring-Closing Metathesis Route and Their Biological Evaluation" @default.
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- W2023447551 doi "https://doi.org/10.1021/jm9001583" @default.
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