Synthesis and biological evaluation of 2-hydroxy derivatives of digitoxigenin and 3-epidigitoxigenin.
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.
Gobbini
M
M
Prassis Istituto di Ricerche Sigma-Tau, Settimo Milanese, MI, Italy.
Marazzi
G
G
Padoani
G
G
Quadri
L
L
Valentino
L
L
Zappavigna
M P
MP
Melloni
P
P
D004073:Digitoxigenin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D000254:Sodium-Potassium-Exchanging ATPase / Q000378:metabolism*; D013329:Structure-Activity Relationship
D004073:Digitoxigenin; D000254:Sodium-Potassium-Exchanging ATPase