8‐Substituted Xanthines as Phosphodiesterase Inhibitors: Conformation‐Dependent Lipophilicity and Structure‐Activity Relationships | Zendy

Walther Bernard | Zendy; Carrupt PierreAlain | Zendy; El Tayar Nabil | Zendy; Testa Bernard | Zendy

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8‐Substituted Xanthines as Phosphodiesterase Inhibitors: Conformation‐Dependent Lipophilicity and Structure‐Activity Relationships

Author(s) -

Walther Bernard,

Carrupt PierreAlain,

El Tayar Nabil,

Testa Bernard

Publication year - 1989

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19890720314

Subject(s) - lipophilicity , chemistry , substituent , quantitative structure–activity relationship , tautomer , potency , caffeine , stereochemistry , phosphodiesterase , enzyme , organic chemistry , biochemistry , in vitro , medicine , endocrinology

The 8‐substituted xanthines 1 – 21 (including compound S 9795), caffeine ( 22 ), and the three isomeric dimethyl‐xanthines 23 – 25 (see Table 1 ), were examined for their lipophilic behaviour using a reversed‐phase HPLC technique. A number of flexible compounds showed a smaller‐than‐expected lipophilicity which based on conformational and tautomeric calculations were ascribed to the predominance of folded forms. A QSAR analysis of the phosphodiesterase‐inhibitory potency of several compounds showed favourable factors to be a low lipophilicity and the absence of a substituent on the N 7 position.

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