Synthesis and structure-activity relationship of some 5-[[(dialkylamino)alkyl]-1-piperidinyl]acetyl]-10,11-dihydro-5H-benzo[b,e][1,4]diazepin-11-ones as M2-selective antimuscarinics

A series of 5-[[[(dialkylamino)alkyl]-1-piperidinyl]acetyl]- 10,11-dihydro-5H-dibenzo[b,e][1,4]-diazepin-11-ones were prepared as potential M2-selective ligands. The compounds were evaluated for their affinity and selectivity for the muscarinic cholinergic receptor. The best M2-selective antimuscari...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1993-01, Vol.36 (1), p.162-165
Main Authors: COHEN, V. I, BAUMGOLD, J, JIN, B, DE LA CRUZ, R, RZESZOTARSKI, W. J, REBA, R. C
Format: Article
Language:English
Subjects:
Animals
Benzodiazepinones - chemical synthesis
Benzodiazepinones - chemistry
Benzodiazepinones - pharmacology
Brain - drug effects
Brain - metabolism
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Mice
Organic chemistry
Parasympatholytics - chemical synthesis
Piperidines - chemical synthesis
Piperidines - chemistry
Piperidines - pharmacology
Pirenzepine - analogs & derivatives
Pirenzepine - pharmacology
Preparations and properties
Rats
Receptors, Muscarinic - drug effects
Receptors, Muscarinic - metabolism
Structure-Activity Relationship
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Summary:A series of 5-[[[(dialkylamino)alkyl]-1-piperidinyl]acetyl]- 10,11-dihydro-5H-dibenzo[b,e][1,4]-diazepin-11-ones were prepared as potential M2-selective ligands. The compounds were evaluated for their affinity and selectivity for the muscarinic cholinergic receptor. The best M2-selective antimuscarinic agent studied is 5-[[4-[4-diethylamino)butyl]-1- piperidinyl]acetyl]-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-11- one, which is approximately 10 times more potent at M2 receptors than previously known compounds such as 11-[[4-[4-(diethylamino)butyl]- 1-piperidinyl]acetyl]-5,11-dihydro-6H- pyrido[2,3-b][1,4]benzodiazepin-6-one (AQ-RA 741).
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00053a021