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Substituted pyridines were synthesized as potential angiotensin II (AII) receptor antagonists. Substitution at the position 2 in the pyridine resulted in potent activity, and the optimal alkyl length was four carbons. The potency further increased with the introduction of a hydroxymethyl group at the position 4. One of the compounds, 2-butyl-6-chloro-4-hydroxymethyl-5-methyl-3-[[2'-(1H-tetrazol-5-yl )biphenyl-4-yl]methyl]pyridine 9 h (KT3-579) is a competitive AII antagonist with a pA2 value of 9.31, and is about 10 times more potent than Du Pont 753. It was found to be an AT1 specific antagonist with an IC50 of 3.09 nM.

Nonpeptide Angiotensin II Receptor Antagonists. I. Synthesis and Biological Activity of Pyridine Derivatives.