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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
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 M1, M2, and M3 muscarinic receptors using [3H] pirenzepine and [3H] NMS as ligands. The binding affinity depend...
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| Published in: | Archiv der Pharmazie (Weinheim) 2003-06, Vol.336 (3), p.143-154 |
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| Main Authors: | , , , , , , , |
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| cites | cdi_FETCH-LOGICAL-c4093-bf5e0bcf9eed4fb00ff4baa227ba45b4f940c1e9498f0e6fc90069c68cea0d243 |
| container_end_page | 154 |
| container_issue | 3 |
| container_start_page | 143 |
| container_title | Archiv der Pharmazie (Weinheim) |
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| creator | Del Giudice, Maria Rosaria Mustazza, Carlo Borioni, Anna Gatta, Franco Tayebati, Khosrow Amenta, Francesco Tucci, Paolo Pieretti, Stefano |
| description | 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 M1, M2, and M3 muscarinic receptors using [3H] pirenzepine and [3H] 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 5l and 6i good M1 and M3 antagonistic properties in vitro and were devoid of cholinergic side effects in vivo. |
| doi_str_mv | 10.1002/ardp.200390013 |
| format | article |
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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 5l and 6i good M1 and M3 antagonistic properties in vitro and were devoid of cholinergic side effects in vivo.</description><identifier>ISSN: 0365-6233</identifier><identifier>EISSN: 1521-4184</identifier><identifier>DOI: 10.1002/ardp.200390013</identifier><identifier>PMID: 12822179</identifier><identifier>CODEN: ARPMAS</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Animals ; Arecoline bioisosteres ; Atropine - pharmacology ; Binding, Competitive ; Biological and medical sciences ; Cholinergic Agents - chemical synthesis ; Cholinergic Agents - chemistry ; Cholinergic Agents - pharmacology ; Cholinergic system ; Guinea Pigs ; Ileum - drug effects ; In Vitro Techniques ; Ligands ; Male ; Medical sciences ; Muscarinic Agonists - pharmacology ; Muscarinic Antagonists - pharmacology ; Muscarinic receptors ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Organ Specificity ; Oxotremorine - pharmacology ; Pharmacology. Drug treatments ; Pyrazoles ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Pyridines - pharmacology ; Rabbits ; Receptors, Muscarinic - drug effects ; Structure-Activity Relationship ; Swine ; Triazoles ; Triazoles - chemical synthesis ; Triazoles - chemistry ; Triazoles - pharmacology ; Urinary Bladder - drug effects ; Vas Deferens - drug effects</subject><ispartof>Archiv der Pharmazie (Weinheim), 2003-06, Vol.336 (3), p.143-154</ispartof><rights>Copyright © 2003 WILEY‐VCH Verlag GmbH & Co. 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Pharm. Pharm. Med. Chem</addtitle><description>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 M1, M2, and M3 muscarinic receptors using [3H] pirenzepine and [3H] 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 5l and 6i good M1 and M3 antagonistic properties in vitro and were devoid of cholinergic side effects in vivo.</description><subject>Animals</subject><subject>Arecoline bioisosteres</subject><subject>Atropine - pharmacology</subject><subject>Binding, Competitive</subject><subject>Biological and medical sciences</subject><subject>Cholinergic Agents - chemical synthesis</subject><subject>Cholinergic Agents - chemistry</subject><subject>Cholinergic Agents - pharmacology</subject><subject>Cholinergic system</subject><subject>Guinea Pigs</subject><subject>Ileum - drug effects</subject><subject>In Vitro Techniques</subject><subject>Ligands</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Muscarinic Agonists - pharmacology</subject><subject>Muscarinic Antagonists - pharmacology</subject><subject>Muscarinic receptors</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Organ Specificity</subject><subject>Oxotremorine - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrazoles</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacology</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Pyridines - pharmacology</subject><subject>Rabbits</subject><subject>Receptors, Muscarinic - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>Swine</subject><subject>Triazoles</subject><subject>Triazoles - chemical synthesis</subject><subject>Triazoles - chemistry</subject><subject>Triazoles - pharmacology</subject><subject>Urinary Bladder - drug effects</subject><subject>Vas Deferens - drug effects</subject><issn>0365-6233</issn><issn>1521-4184</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNqFkUtvEzEUhS0EomlgyxJ5A6JSHPyaSbzsG6SkQCliaXk818QwmRnsmcDwn_iPOE3UdsfGtq6_c659D0IvGJ0ySvlbE8p2yikVilImHqERyzgjks3lYzSiIs9IzoU4QIcxfqcJozx7ig4Yn3POZmqE_n4e6m4F0UfcOMzIErrVUJGMvGmHYP40FREEm7rEqZTqt0c2wXyCJemCf0hsgSOyuxQTnJMOumBWQxma5OVLXwM-g-A3pvMbiLeamxX4gM83pupTtamxiXjZR2uCr73F12Ch7ZqAF_5bwuMz9MSZKsLz_T5GXy7Ob07fkcWHy_enxwtiJVWCFC4DWlinAErpCkqdk4UxnM8KI7NCOiWpZaCkmjsKubNpeLmy-dyCoSWXYoxe73zb0PzsIXZ67aOFqjI1NH3UMyGUlGkdo-kOtKGJMYDTbfBrEwbNqN4GpLcB6buAkuDl3rkv1lDe4_tEEvBqD5g0hsoFU1sf7zk5VyLPt0Zqx_3yFQz_aauPr88-PnwE2Wl97OD3ndaEHzqfiVmmv15dpj-esJNPV0t9If4BOTm3GA</recordid><startdate>200306</startdate><enddate>200306</enddate><creator>Del Giudice, Maria Rosaria</creator><creator>Mustazza, Carlo</creator><creator>Borioni, Anna</creator><creator>Gatta, Franco</creator><creator>Tayebati, Khosrow</creator><creator>Amenta, Francesco</creator><creator>Tucci, Paolo</creator><creator>Pieretti, Stefano</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>200306</creationdate><title>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</title><author>Del Giudice, Maria Rosaria ; Mustazza, Carlo ; Borioni, Anna ; Gatta, Franco ; Tayebati, Khosrow ; Amenta, Francesco ; Tucci, Paolo ; Pieretti, Stefano</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4093-bf5e0bcf9eed4fb00ff4baa227ba45b4f940c1e9498f0e6fc90069c68cea0d243</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Animals</topic><topic>Arecoline bioisosteres</topic><topic>Atropine - pharmacology</topic><topic>Binding, Competitive</topic><topic>Biological and medical sciences</topic><topic>Cholinergic Agents - chemical synthesis</topic><topic>Cholinergic Agents - chemistry</topic><topic>Cholinergic Agents - pharmacology</topic><topic>Cholinergic system</topic><topic>Guinea Pigs</topic><topic>Ileum - drug effects</topic><topic>In Vitro Techniques</topic><topic>Ligands</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Muscarinic Agonists - pharmacology</topic><topic>Muscarinic Antagonists - pharmacology</topic><topic>Muscarinic receptors</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Organ Specificity</topic><topic>Oxotremorine - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrazoles</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacology</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Pyridines - pharmacology</topic><topic>Rabbits</topic><topic>Receptors, Muscarinic - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>Swine</topic><topic>Triazoles</topic><topic>Triazoles - chemical synthesis</topic><topic>Triazoles - chemistry</topic><topic>Triazoles - pharmacology</topic><topic>Urinary Bladder - drug effects</topic><topic>Vas Deferens - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Del Giudice, Maria Rosaria</creatorcontrib><creatorcontrib>Mustazza, Carlo</creatorcontrib><creatorcontrib>Borioni, Anna</creatorcontrib><creatorcontrib>Gatta, Franco</creatorcontrib><creatorcontrib>Tayebati, Khosrow</creatorcontrib><creatorcontrib>Amenta, Francesco</creatorcontrib><creatorcontrib>Tucci, Paolo</creatorcontrib><creatorcontrib>Pieretti, Stefano</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Archiv der Pharmazie (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Del Giudice, Maria Rosaria</au><au>Mustazza, Carlo</au><au>Borioni, Anna</au><au>Gatta, Franco</au><au>Tayebati, Khosrow</au><au>Amenta, Francesco</au><au>Tucci, Paolo</au><au>Pieretti, Stefano</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>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</atitle><jtitle>Archiv der Pharmazie (Weinheim)</jtitle><addtitle>Arch. Pharm. Pharm. Med. Chem</addtitle><date>2003-06</date><risdate>2003</risdate><volume>336</volume><issue>3</issue><spage>143</spage><epage>154</epage><pages>143-154</pages><issn>0365-6233</issn><eissn>1521-4184</eissn><coden>ARPMAS</coden><abstract>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 M1, M2, and M3 muscarinic receptors using [3H] pirenzepine and [3H] 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 5l and 6i good M1 and M3 antagonistic properties in vitro and were devoid of cholinergic side effects in vivo.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>12822179</pmid><doi>10.1002/ardp.200390013</doi><tpages>12</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0365-6233 |
| ispartof | Archiv der Pharmazie (Weinheim), 2003-06, Vol.336 (3), p.143-154 |
| issn | 0365-6233 1521-4184 |
| language | eng |
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| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Animals Arecoline bioisosteres Atropine - pharmacology Binding, Competitive Biological and medical sciences Cholinergic Agents - chemical synthesis Cholinergic Agents - chemistry Cholinergic Agents - pharmacology Cholinergic system Guinea Pigs Ileum - drug effects In Vitro Techniques Ligands Male Medical sciences Muscarinic Agonists - pharmacology Muscarinic Antagonists - pharmacology Muscarinic receptors Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Organ Specificity Oxotremorine - pharmacology Pharmacology. Drug treatments Pyrazoles Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Pyridines - chemical synthesis Pyridines - chemistry Pyridines - pharmacology Rabbits Receptors, Muscarinic - drug effects Structure-Activity Relationship Swine Triazoles Triazoles - chemical synthesis Triazoles - chemistry Triazoles - pharmacology Urinary Bladder - drug effects Vas Deferens - drug effects |
| title | 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 |
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