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  • Synthesis and biological evaluation of 2-hydroxy derivatives of digitoxigenin and 3-epidigitoxigenin.

Synthesis and biological evaluation of 2-hydroxy derivatives of digitoxigenin and 3-epidigitoxigenin.

Bioorganic & medicinal chemistry (1998-12-05)
M Gobbini, G Marazzi, G Padoani, L Quadri, L Valentino, M P Zappavigna, P Melloni
ABSTRACT

The four stereoisomers of the 2-hydroxy derivatives of digitoxigenin and 3-epidigitoxigenin have been synthesized, their structures established by NMR, and their binding affinity for the digitalis receptor on Na+, K(+)-ATPase evaluated. These derivatives showed lower affinities than the parent compounds. The hydrophilic hydroxy groups in the alpha position are more detrimental to the affinity than hydroxy groups in the beta position.

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Lithium tri-tert-butoxyaluminum hydride solution, 1.0 M in THF
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Sigma-Aldrich
Digitoxigenin
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