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Design, synthesis, and structure-activity relationship study of bicyclic piperazine analogs of indole-3-carboxamides as novel cannabinoid CB1 receptor agonists.
- Source :
-
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2010 Dec 15; Vol. 20 (24), pp. 7327-30. Date of Electronic Publication: 2010 Oct 20. - Publication Year :
- 2010
-
Abstract
- Bicyclic piperazine derivatives were synthesized as conformationally constrained analogs of N-alkyl piperazines and were found to be potent CB1 receptor agonists. The CB1 receptor agonist activity was dependent upon the absolute configuration of the chiral center of the bicyclic ring system. Although the conformational constraint did not protect the compounds from metabolism by N-dealkylation, several bicyclic analogs were found to be more potent than the unconstrained lead compound. Compound 8b demonstrated potent antinociceptive activity in vivo.<br /> (Copyright © 2010 Elsevier Ltd. All rights reserved.)
- Subjects :
- Animals
Azabicyclo Compounds chemistry
Azabicyclo Compounds pharmacology
Drug Design
Humans
Indoles chemistry
Indoles pharmacology
Mice
Microsomes, Liver metabolism
Piperazines chemical synthesis
Piperazines pharmacology
Receptor, Cannabinoid, CB1 metabolism
Structure-Activity Relationship
Amides chemistry
Azabicyclo Compounds chemical synthesis
Bridged Bicyclo Compounds chemistry
Indoles chemical synthesis
Piperazines chemistry
Receptor, Cannabinoid, CB1 agonists
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3405
- Volume :
- 20
- Issue :
- 24
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry letters
- Publication Type :
- Academic Journal
- Accession number :
- 21074434
- Full Text :
- https://doi.org/10.1016/j.bmcl.2010.10.061