Synthesis of 1-Methyl-5-(pyrazol-3- and -5-yl- and 1, 2, 4-triazol-3- and 5-yl)-1, 2, 3, 6-tetrahydropyridine Derivatives and Their Evaluation as Muscarinic Receptor Ligands
| Autor: | Franco Gatta, Francesco Amenta, Khosrow Tayebati, Anna Borioni, Maria Rosaria Del Giudice, Stefano Pieretti, Paolo Tucci, Carlo Mustazza |
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| Rok vydání: | 2003 |
| Předmět: |
Atropine
Male Pyridines Swine Stereochemistry Guinea Pigs Urinary Bladder Cholinergic Agents Pharmaceutical Science Muscarinic Antagonists In Vitro Techniques Muscarinic Agonists Ligands Binding Competitive Structure-Activity Relationship chemistry.chemical_compound Vas Deferens Ileum In vivo Drug Discovery Muscarinic acetylcholine receptor medicine Animals Arecoline Functional studies M.2 Oxotremorine Muscarinic acetylcholine receptor M3 General Medicine Triazoles Receptors Muscarinic Pirenzepine In vitro chemistry Organ Specificity Pyrazoles Cholinergic Rabbits Bioisostere medicine.drug |
| Zdroj: | Archiv der Pharmazie. 336:143-154 |
| ISSN: | 1521-4184 0365-6233 |
| DOI: | 10.1002/ardp.200390013 |
| Popis: | A series of 1-methyl-5-(pyrazol-3- and -5-yl- and 1,2,4-triazol-3- and 5-yl)-1,2,3,6-tetrahydropyridine derivatives structurally related to arecoline were synthesized and evaluated on M 1 , M 2 , and M 3 muscarinic receptors using [ 3 H]pirenzepine and [ 3 H]NMS as ligands. The binding affinity depended on the position and size of the substituents. The most interesting compounds were further evaluated in functional studies on isolated organs and in vivo for cholinergic side effects. Compounds 51 and 6 i displayed good M 1 and M 3 antagonistic properties in vitro and were devoid of cholinergic side effects in vivo. |
| Databáze: | OpenAIRE |
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