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Molecules 1998, 3(1), 20-25; doi:10.3390/30100020

Synthesis and Biological Evaluation of 14 -Methoxy Digitalis Derivatives

Prassis Istituto di Ricerche Sigma-Tau, Via Forlanini, 3, 20019 Settimo Milanese (MI), Italy
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Received: 11 November 1997 / Accepted: 15 January 1998 / Published: 25 January 1998
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Abstract

The synthesis and biological evaluation of 14β-methoxy derivatives of digitoxigenin and of other digitalis-like compounds are reported. These compounds have a 14β-oxygen, which can be a hydrogen bonding acceptor, as is the case of 14β,15β-epoxide derivatives, but not a hydrogen bonding donor as is the case of 14β-hydroxy derivatives. All the new 14β-methoxy derivatives show a considerable reduced binding affinity on Na+,K+-ATPase when compared with the 14β-hydroxy analogues and also with the 14β,15β-epoxy derivatives. These results could mean that the digitalis receptor does not permit the presence of a bulky substituent in the 14β region, even of relatively small volume like the methyl group
Keywords: 14b-Methoxy digitalis derivatives; binding affinity; Na+; K+-ATPase 14b-Methoxy digitalis derivatives; binding affinity; Na+; K+-ATPase
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Gobbini, M.; Almirante, N.; Cerri, A.; Padoani, G.; Melloni, P. Synthesis and Biological Evaluation of 14 -Methoxy Digitalis Derivatives. Molecules 1998, 3, 20-25.

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