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Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists
Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1– 4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is high...
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| Published in: | Farmaco (Società chimica italiana : 1989) 1999-06, Vol.54 (6), p.364-374 |
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| Main Authors: | , , , , , , , , , , , , , , , , |
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| cited_by | cdi_FETCH-LOGICAL-c390t-5165331f075aa35c5806619c04ef7a0b7fcbbb7fa03d930d82f35181e2fa2ba93 |
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| cites | cdi_FETCH-LOGICAL-c390t-5165331f075aa35c5806619c04ef7a0b7fcbbb7fa03d930d82f35181e2fa2ba93 |
| container_end_page | 374 |
| container_issue | 6 |
| container_start_page | 364 |
| container_title | Farmaco (Società chimica italiana : 1989) |
| container_volume | 54 |
| creator | Giardina, G.A.M Artico, M Cavagnera, S Cerri, A Consolandi, E Gagliardi, S Graziani, D Grugni, M Hay, D.W.P Luttmann, M.A Mena, R Raveglia, L.F Rigolio, R Sarau, H.M Schmidt, D.B Zanoni, G Farina, C |
| description | Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists
1–
4 of general formula
I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (
5,
6,
10 and
13) and compound
5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. |
| doi_str_mv | 10.1016/S0014-827X(99)00043-9 |
| format | article |
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1–
4 of general formula
I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (
5,
6,
10 and
13) and compound
5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline.</description><identifier>ISSN: 0014-827X</identifier><identifier>EISSN: 1879-0569</identifier><identifier>DOI: 10.1016/S0014-827X(99)00043-9</identifier><identifier>PMID: 10443017</identifier><language>eng</language><publisher>Lausanne: Elsevier SAS</publisher><subject>2-Phenyl-4-quinolinecarboxamides ; Animals ; Binding, Competitive - drug effects ; Biological and medical sciences ; CHO Cells ; Cloning, Molecular ; Cricetinae ; Humans ; Medical sciences ; Neurokinin B ; Neurokinin-3 receptor antagonists ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems ; Pharmacology. Drug treatments ; Quinolines - chemical synthesis ; Quinolines - pharmacology ; Radioligand Assay ; Receptors, Neurokinin-3 - antagonists & inhibitors ; Structure-Activity Relationship ; Tachykinins</subject><ispartof>Farmaco (Società chimica italiana : 1989), 1999-06, Vol.54 (6), p.364-374</ispartof><rights>1999 Elsevier Science S.A.</rights><rights>1999 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-5165331f075aa35c5806619c04ef7a0b7fcbbb7fa03d930d82f35181e2fa2ba93</citedby><cites>FETCH-LOGICAL-c390t-5165331f075aa35c5806619c04ef7a0b7fcbbb7fa03d930d82f35181e2fa2ba93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1896389$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10443017$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Giardina, G.A.M</creatorcontrib><creatorcontrib>Artico, M</creatorcontrib><creatorcontrib>Cavagnera, S</creatorcontrib><creatorcontrib>Cerri, A</creatorcontrib><creatorcontrib>Consolandi, E</creatorcontrib><creatorcontrib>Gagliardi, S</creatorcontrib><creatorcontrib>Graziani, D</creatorcontrib><creatorcontrib>Grugni, M</creatorcontrib><creatorcontrib>Hay, D.W.P</creatorcontrib><creatorcontrib>Luttmann, M.A</creatorcontrib><creatorcontrib>Mena, R</creatorcontrib><creatorcontrib>Raveglia, L.F</creatorcontrib><creatorcontrib>Rigolio, R</creatorcontrib><creatorcontrib>Sarau, H.M</creatorcontrib><creatorcontrib>Schmidt, D.B</creatorcontrib><creatorcontrib>Zanoni, G</creatorcontrib><creatorcontrib>Farina, C</creatorcontrib><title>Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists</title><title>Farmaco (Società chimica italiana : 1989)</title><addtitle>Farmaco</addtitle><description>Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists
1–
4 of general formula
I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (
5,
6,
10 and
13) and compound
5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline.</description><subject>2-Phenyl-4-quinolinecarboxamides</subject><subject>Animals</subject><subject>Binding, Competitive - drug effects</subject><subject>Biological and medical sciences</subject><subject>CHO Cells</subject><subject>Cloning, Molecular</subject><subject>Cricetinae</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Neurokinin B</subject><subject>Neurokinin-3 receptor antagonists</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - pharmacology</subject><subject>Radioligand Assay</subject><subject>Receptors, Neurokinin-3 - antagonists & inhibitors</subject><subject>Structure-Activity Relationship</subject><subject>Tachykinins</subject><issn>0014-827X</issn><issn>1879-0569</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><recordid>eNqFkEuLFDEQgIMo7rj6E5QcRPQQTTqd7uS0yOILFwUf4C1WpytupDvpTTLi_Ht7dobVm5cqivrqwUfIQ8GfCy66F585Fy3TTf_tqTHPOOetZOYW2QjdG8ZVZ26TzQ1yQu6V8nMt-77r75ITwdtWrtWGfP-EywQOZ4yVJk_rJdKrbYhpChFp2ZWKMw2RNmy5xLibWMtu2g7ykH7DHEakH94zSTM6XGrKFGKFHymGUst9csfDVPDBMZ-Sr69ffTl_yy4-vnl3_vKCOWl4ZUp0Skrhea8ApHJK864TxvEWfQ986L0bhjUCl6ORfNSNl0pogY2HZgAjT8mTw94lp6stlmrnUBxOE0RM22I7Y5RSWq-gOoAup1IyervkMEPeWcHtXq29Vmv33qwx9lqt3R94dDywHWYc_5k6uFyBx0cAioPJZ4gulL-cNp3U-z1nBwxXG78CZltcwOhwDKu_ascU_vPJH_5rll8</recordid><startdate>19990630</startdate><enddate>19990630</enddate><creator>Giardina, G.A.M</creator><creator>Artico, M</creator><creator>Cavagnera, S</creator><creator>Cerri, A</creator><creator>Consolandi, E</creator><creator>Gagliardi, S</creator><creator>Graziani, D</creator><creator>Grugni, M</creator><creator>Hay, D.W.P</creator><creator>Luttmann, M.A</creator><creator>Mena, R</creator><creator>Raveglia, L.F</creator><creator>Rigolio, R</creator><creator>Sarau, H.M</creator><creator>Schmidt, D.B</creator><creator>Zanoni, G</creator><creator>Farina, C</creator><general>Elsevier SAS</general><general>Elsevier Science</general><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>19990630</creationdate><title>Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists</title><author>Giardina, G.A.M ; Artico, M ; Cavagnera, S ; Cerri, A ; Consolandi, E ; Gagliardi, S ; Graziani, D ; Grugni, M ; Hay, D.W.P ; Luttmann, M.A ; Mena, R ; Raveglia, L.F ; Rigolio, R ; Sarau, H.M ; Schmidt, D.B ; Zanoni, G ; Farina, C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-5165331f075aa35c5806619c04ef7a0b7fcbbb7fa03d930d82f35181e2fa2ba93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>2-Phenyl-4-quinolinecarboxamides</topic><topic>Animals</topic><topic>Binding, Competitive - drug effects</topic><topic>Biological and medical sciences</topic><topic>CHO Cells</topic><topic>Cloning, Molecular</topic><topic>Cricetinae</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Neurokinin B</topic><topic>Neurokinin-3 receptor antagonists</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinolines - chemical synthesis</topic><topic>Quinolines - pharmacology</topic><topic>Radioligand Assay</topic><topic>Receptors, Neurokinin-3 - antagonists & inhibitors</topic><topic>Structure-Activity Relationship</topic><topic>Tachykinins</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Giardina, G.A.M</creatorcontrib><creatorcontrib>Artico, M</creatorcontrib><creatorcontrib>Cavagnera, S</creatorcontrib><creatorcontrib>Cerri, A</creatorcontrib><creatorcontrib>Consolandi, E</creatorcontrib><creatorcontrib>Gagliardi, S</creatorcontrib><creatorcontrib>Graziani, D</creatorcontrib><creatorcontrib>Grugni, M</creatorcontrib><creatorcontrib>Hay, D.W.P</creatorcontrib><creatorcontrib>Luttmann, M.A</creatorcontrib><creatorcontrib>Mena, R</creatorcontrib><creatorcontrib>Raveglia, L.F</creatorcontrib><creatorcontrib>Rigolio, R</creatorcontrib><creatorcontrib>Sarau, H.M</creatorcontrib><creatorcontrib>Schmidt, D.B</creatorcontrib><creatorcontrib>Zanoni, G</creatorcontrib><creatorcontrib>Farina, C</creatorcontrib><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>Farmaco (Società chimica italiana : 1989)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Giardina, G.A.M</au><au>Artico, M</au><au>Cavagnera, S</au><au>Cerri, A</au><au>Consolandi, E</au><au>Gagliardi, S</au><au>Graziani, D</au><au>Grugni, M</au><au>Hay, D.W.P</au><au>Luttmann, M.A</au><au>Mena, R</au><au>Raveglia, L.F</au><au>Rigolio, R</au><au>Sarau, H.M</au><au>Schmidt, D.B</au><au>Zanoni, G</au><au>Farina, C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists</atitle><jtitle>Farmaco (Società chimica italiana : 1989)</jtitle><addtitle>Farmaco</addtitle><date>1999-06-30</date><risdate>1999</risdate><volume>54</volume><issue>6</issue><spage>364</spage><epage>374</epage><pages>364-374</pages><issn>0014-827X</issn><eissn>1879-0569</eissn><abstract>Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists
1–
4 of general formula
I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (
5,
6,
10 and
13) and compound
5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline.</abstract><cop>Lausanne</cop><pub>Elsevier SAS</pub><pmid>10443017</pmid><doi>10.1016/S0014-827X(99)00043-9</doi><tpages>11</tpages></addata></record> |
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| identifier | ISSN: 0014-827X |
| ispartof | Farmaco (Società chimica italiana : 1989), 1999-06, Vol.54 (6), p.364-374 |
| issn | 0014-827X 1879-0569 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_69955588 |
| source | Elsevier |
| subjects | 2-Phenyl-4-quinolinecarboxamides Animals Binding, Competitive - drug effects Biological and medical sciences CHO Cells Cloning, Molecular Cricetinae Humans Medical sciences Neurokinin B Neurokinin-3 receptor antagonists Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Quinolines - chemical synthesis Quinolines - pharmacology Radioligand Assay Receptors, Neurokinin-3 - antagonists & inhibitors Structure-Activity Relationship Tachykinins |
| title | Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists |
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