Abstract:
:The synthesis of seco-D and D-homo digitalis derivatives, from the carda-14,20(22)-dienolide 1, is described. Selective ozonolysis gave the seco-D 14-ketoaldehyde 2a. Modification of the two carbonyl groups and of the alpha, beta-unsaturated lactone ring of the seco-D 14-ketoaldehyde 2a allowed preparation of derivatives with a broad range of binding affinity to the Na+, K(+)-ATPase receptor. Some of the seco-D derivatives (10, 11b, and 13b) showed a binding affinity similar to that of digitoxigenin, demonstrating that the D-ring is not essential for recognition by the digitalis receptor. In the class of D-homo derivatives the highest binding value, about 15 times lower than that of digitoxigenin, was that of the C/D cis compound 29b; the C/D trans analog 28b showed a 7-fold decrease in binding affinity, indicating that the C/D configuration plays an important role in D-homo derivatives as in the classical digitalis compounds.
journal_name
Steroidsjournal_title
Steroidsauthors
Gobbini M,Benicchio A,Marazzi G,Padoani G,Torri M,Melloni Pdoi
10.1016/s0039-128x(96)00117-1subject
Has Abstractpub_date
1996-10-01 00:00:00pages
572-82issue
10eissn
0039-128Xissn
1878-5867pii
S0039-128X(96)00117-1journal_volume
61pub_type
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