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1‐Pentanoyl‐ N ‐{[2'‐(1 H ‐tetrazol‐5‐yl)biphenyl‐4‐yl]methyl}‐pyrrolidine‐2‐carboxamide: Investigation of Structural Variations
Author(s) -
Catalano Alessia,
Carocci Alessia,
Di Mola Antonia,
Bruno Claudio,
Vanderheyden Patrick M. L.,
Franchini Carlo
Publication year - 2011
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201000296
Subject(s) - carboxamide , pyrrolidine , chemistry , stereochemistry , tetrazole , biphenyl , moiety , chemical synthesis , receptor , in vitro , biochemistry , organic chemistry
We recently reported a series of 1‐acyl‐ N ‐(biphenyl‐4‐ylmethyl)pyrrolidine‐2‐carboxamides as AT 1 receptor ligands. The most potent compound of the series, 1‐pentanoyl‐ N ‐{[2'‐(1 H ‐tetrazol‐5‐yl)biphenyl‐4‐yl]methyl}‐pyrrolidine‐2‐carboxamide, showed an interesting affinity for the receptor. To investigate the influence of structure variations on affinity, the synthesis of additional compounds belonging to this series has been performed. Biological tests run on the newly synthesized compounds on CHO‐hAT 1 cells stably expressing the human AT 1 receptor confirm our previous hypothesis, i.e. that, within this series, the length of the acyl chain, the substitution of the amidic group and the nature of the acidic one are crucial for the receptor interaction, being a valeric chain, a secondary amidic function and the tetrazole moiety, respectively, the optimal ones.