Analogues of 3-Quinuclidinyl Benzilate

Article abstract of DOI:10.1021/jm00351a020

A number of analogues of 3-quinuclidinyl benzilate (QNB) have been synthesized and their affinities to muscarinic receptor from rat or dog ventricular muscle measured.We have determined that the muscarinic receptor can to a different degree accomodate either a halogen in the ortho, meta, or para position of one phenyl ring or the repalcement of one phenyl ring with an alkyl group.Our in vitro competition studies show that the affinities lie within a 270-fold range, from the highest affinity compound, 3-quinuclidinyl α-hydroxy-α-cyclopentylphenylacetate (2), to the lowest affinity compound, 3-quinuclidinyl α-hydroxy-α-2-propargylphenylacetate (11).