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.
Section of Radiopharmaceutical Chemistry, George Washington University Medical Center, Washington, D.C. 20037.
V I
VI
Cohen
R E
RE
Gibson
L H
LH
Fan
R
R
De La Cruz
M S
MS
Gitler
E
E
Hariman
R C
RC
Reba
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