2-Substituted 1-azabicycloalkanes, a new class of non-opiate antinociceptive agents

2-Substituted 1-azabicycloalkanes (3- and 5-aryloctahydroindolizines 2 and 11, 3-cyclohexyloctahydroindolizine 12, 4-aryloctahydroquinolizines 13, and 3-arylhexahydropyrrolizines 14) constitute a new class of non-opiate antinociceptive agents. These compounds demonstrated activity in the mouse abdom...

Full description

Saved in:
Bibliographic Details
Published in:Journal of medicinal chemistry 1992-07, Vol.35 (15), p.2855-2863
Main Authors: Carson, John R, Carmosin, Richard J, Vaught, Jeffry L, Gardocki, Joseph F, Costanzo, Michael J, Raffa, Robert B, Almond, Harold R
Format: Article
Language:English
Subjects:
Analgesics - chemistry
Analgesics - pharmacology
Animals
Chemistry
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indolizines - chemical synthesis
Indolizines - pharmacology
Mice
Organic chemistry
Organic compounds
Physics
Preparations and properties
Pyrrolizidine Alkaloids - chemical synthesis
Pyrrolizidine Alkaloids - pharmacology
Quinolizines - chemical synthesis
Quinolizines - pharmacology
Rats
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
Structure-Activity Relationship
X-Ray Diffraction
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:2-Substituted 1-azabicycloalkanes (3- and 5-aryloctahydroindolizines 2 and 11, 3-cyclohexyloctahydroindolizine 12, 4-aryloctahydroquinolizines 13, and 3-arylhexahydropyrrolizines 14) constitute a new class of non-opiate antinociceptive agents. These compounds demonstrated activity in the mouse abdominal constriction test and many were active in the mouse tail-flick test. trans-3-(2-Bromophenyl)octahydroindolizine (2a) did not bind to the opiate receptor nor did it affect arachidonate metabolism. 3-Aryloctahydroindolizines were prepared by catalytic hydrogenation of 1-aryl-3-(2-pyridinyl)-2-propen-1-ones. The X-ray crystal structure of (-)-2a was determined and absolute stereochemistry assigned as 3-R,8a-R.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00093a019