1-pentanoyl-N-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-pyrrolidine-2-carboxamide: investigation of structural variations

Alessia Catalano, Alessia Carocci, Antonia Di Mola, Claudio Bruno, Patrick M L Vanderheyden, Carlo Franchini

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

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'-(1H-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.

Original languageEnglish
Pages (from-to)617-26
Number of pages10
JournalArchiv der Pharmazie
Volume344
Issue number9
DOIs
Publication statusPublished - Sep 2011

Keywords

  • Angiotensin Receptor Antagonists
  • Animals
  • Biphenyl Compounds
  • CHO Cells
  • Cricetinae
  • Humans
  • Ligands
  • Losartan
  • Molecular Structure
  • Protein Binding
  • Pyrrolidines
  • Receptor, Angiotensin, Type 1
  • Tetrazoles

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