Synthesis of 5-(4-Alkoxy-[1,2,5]thiadiazol-3-yl)-3-methyl-1,2,3,4- tetrahydropyrimidine Oxalate Salts and Their Evaluation as Muscarinic Receptor Agonists

Park, Jewn-Giew; Lee, Mi-Jeoung; Kong, Jae Yang; Jung, Myung Hun

doi:10.1002/(sici)1521-4184(20005)333:5<113::aid-ardp113>3.3.co;2-0

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“…Over the past few years the naturally occurring muscarinic agonist arecoline [9] (1-methyl-5-methoxycarbonyl-1,2,3,6-tetrahydropyridine) has been a template for the preparation of new muscarinic ligands bearing a heterocyclic ring in substitution of the labile arecoline ester group.Thus arecoline bioisosteres bearing a thiadiazole [10,11], oxadiazole [12], tetrazole, or 1,2,3-triazole [13] ring were studied for affinities to M 1 -M 3 receptors, while at present the corresponding pyrazoles [14] and [1,2,4]triazoles were only partially investigated.…”

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confidence: 99%

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

Giudice¹,

Mustazza²,

Borioni³

et al. 2003

Archiv der Pharmazie

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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 5 l and 6 i good M(1) and M(3) antagonistic properties in vitro and were devoid of cholinergic side effects in vivo.

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