Synthesis and muscarinic cholinergic receptor affinities of 3-quinuclidinyl alpha-(alkoxyalkyl)-alpha-aryl-alpha-hydroxyacetates.
Seven analogues of 3-quinuclidinyl benzilate (QNB) in which one phenyl ring was replaced by an alkoxyalkyl moiety were synthesized and their affinities for the muscarinic cholinergic receptor determined. An oxygen in the beta-position of the moiety was not well-tolerated. By contrast, an oxygen in the gamma-position did not change the affinity for the muscarinic receptor. However, when a bromine was placed on the remaining phenyl ring, the affinity was significantly reduced in striking contrast to results obtained on halogenation of QNB.
Cohen
V I
VI
Section of Radiopharmaceutical Chemistry, George Washington University Medical Center, Washington, D.C. 20037.
Gibson
R E
RE
Fan
L H
LH
De La Cruz
R
R
Gitler
M S
MS
Hariman
E
E
Reba
R C
RC
D000818:Animals; D001966:Bromine; D003342:Corpus Striatum / Q000737:chemistry; D007457:Iodine Radioisotopes; D008297:Male; D015394:Molecular Structure; D011813:Quinuclidinyl Benzilate / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D051381:Rats; D011919:Rats, Inbred Strains; D011976:Receptors, Muscarinic / Q000378:metabolism*; D013329:Structure-Activity Relationship
D007457:Iodine Radioisotopes; D011976:Receptors, Muscarinic; D011813:Quinuclidinyl Benzilate; C040062:3-quinuclidinyl-4-iodobenzilate; D001966:Bromine