Discovery of α-amidosulfones as potent and selective agonists of CB2 : Synthesis, SAR, and pharmacokinetic properties

A series of alpha-amidosulfones were found to be potent and selective agonists of CB(2). The discovery, synthesis, and structure-activity relationships of this series of agonists are reported. In addition, the pharmacokinetic properties of the most promising compounds are profiled.

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Bioorganic & medicinal chemistry letters 2009, Vol.19 (1), p.31-35
Hauptverfasser: MARX, Isaac E, DIMAURO, Erin F, MARTIN, Matthew W, WHITE, Ryan D, FREMEAU, Robert T, PATEL, Vinod F, CHENG, Alan, EMKEY, Renee, HITCHCOCK, Stephen A, LIYUE HUANG, HUANG, Ming Y, HUMAN, Jason, LEE, Josie H, XINGWEN LI
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 35
container_issue 1
container_start_page 31
container_title Bioorganic & medicinal chemistry letters
container_volume 19
creator MARX, Isaac E
DIMAURO, Erin F
MARTIN, Matthew W
WHITE, Ryan D
FREMEAU, Robert T
PATEL, Vinod F
CHENG, Alan
EMKEY, Renee
HITCHCOCK, Stephen A
LIYUE HUANG
HUANG, Ming Y
HUMAN, Jason
LEE, Josie H
XINGWEN LI
description A series of alpha-amidosulfones were found to be potent and selective agonists of CB(2). The discovery, synthesis, and structure-activity relationships of this series of agonists are reported. In addition, the pharmacokinetic properties of the most promising compounds are profiled.
doi_str_mv 10.1016/j.bmcl.2008.11.026
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_66770045</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>20345759</sourcerecordid><originalsourceid>FETCH-LOGICAL-c362t-6b3ccb0c3d14341c5ddd303e1223acaad5cc8f5f641a2766e02911ef337548713</originalsourceid><addsrcrecordid>eNqFkcFu1DAQhi0EokvhBTggX-DUhBnbcTbcygItUiUkChI3y-tMqJckTjPZlfax-iI8E1m6gmNPc_n-_9foE-IlQo6A9u0mX3ehzRXAMkfMQdlHYoHGmkwbKB6LBVQWsmVlfpyIZ8wbADRgzFNxghVYpUqzELsPkUPa0biXqZG_7zLfxTrxtm1STyw9yyFN1E_S97VkailMcUfS_0x95IkPodV7Jd_J630_3RBHPpPX51_P_vLDjR87H9Kv2NMUgxzGNNA4ReLn4knjW6YXx3sqvn_6-G11mV19ufi8Or_KgrZqyuxah7CGoGs02mAo6rrWoAmV0j54XxchLJuisQa9Kq0lUBUiNVqXhVmWqE_Fm_veefp2Szy5bv6X2tb3lLbsrC1LAFM8CCrQpiiLagbVPRjGxDxS44Yxdn7cOwR30OI27qDFHbQ4RDdrmUOvju3bdUf1_8jRwwy8PgKeg2-b0fch8j9OIei5Tuk_XEaX0g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>20345759</pqid></control><display><type>article</type><title>Discovery of α-amidosulfones as potent and selective agonists of CB2 : Synthesis, SAR, and pharmacokinetic properties</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals</source><creator>MARX, Isaac E ; DIMAURO, Erin F ; MARTIN, Matthew W ; WHITE, Ryan D ; FREMEAU, Robert T ; PATEL, Vinod F ; CHENG, Alan ; EMKEY, Renee ; HITCHCOCK, Stephen A ; LIYUE HUANG ; HUANG, Ming Y ; HUMAN, Jason ; LEE, Josie H ; XINGWEN LI</creator><creatorcontrib>MARX, Isaac E ; DIMAURO, Erin F ; MARTIN, Matthew W ; WHITE, Ryan D ; FREMEAU, Robert T ; PATEL, Vinod F ; CHENG, Alan ; EMKEY, Renee ; HITCHCOCK, Stephen A ; LIYUE HUANG ; HUANG, Ming Y ; HUMAN, Jason ; LEE, Josie H ; XINGWEN LI</creatorcontrib><description>A series of alpha-amidosulfones were found to be potent and selective agonists of CB(2). The discovery, synthesis, and structure-activity relationships of this series of agonists are reported. In addition, the pharmacokinetic properties of the most promising compounds are profiled.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2008.11.026</identifier><identifier>PMID: 19062274</identifier><language>eng</language><publisher>Amsterdam: Elsevier</publisher><subject>Amides - chemistry ; Amides - pharmacology ; Animals ; Biological and medical sciences ; Humans ; Medical sciences ; Microsomes, Liver ; Miscellaneous ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Pharmacokinetics ; Pharmacology. Drug treatments ; Rats ; Receptor, Cannabinoid, CB2 - agonists ; Structure-Activity Relationship ; Sulfones - chemistry ; Sulfones - pharmacology</subject><ispartof>Bioorganic &amp; medicinal chemistry letters, 2009, Vol.19 (1), p.31-35</ispartof><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-6b3ccb0c3d14341c5ddd303e1223acaad5cc8f5f641a2766e02911ef337548713</citedby><cites>FETCH-LOGICAL-c362t-6b3ccb0c3d14341c5ddd303e1223acaad5cc8f5f641a2766e02911ef337548713</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=21030082$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19062274$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>MARX, Isaac E</creatorcontrib><creatorcontrib>DIMAURO, Erin F</creatorcontrib><creatorcontrib>MARTIN, Matthew W</creatorcontrib><creatorcontrib>WHITE, Ryan D</creatorcontrib><creatorcontrib>FREMEAU, Robert T</creatorcontrib><creatorcontrib>PATEL, Vinod F</creatorcontrib><creatorcontrib>CHENG, Alan</creatorcontrib><creatorcontrib>EMKEY, Renee</creatorcontrib><creatorcontrib>HITCHCOCK, Stephen A</creatorcontrib><creatorcontrib>LIYUE HUANG</creatorcontrib><creatorcontrib>HUANG, Ming Y</creatorcontrib><creatorcontrib>HUMAN, Jason</creatorcontrib><creatorcontrib>LEE, Josie H</creatorcontrib><creatorcontrib>XINGWEN LI</creatorcontrib><title>Discovery of α-amidosulfones as potent and selective agonists of CB2 : Synthesis, SAR, and pharmacokinetic properties</title><title>Bioorganic &amp; medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of alpha-amidosulfones were found to be potent and selective agonists of CB(2). The discovery, synthesis, and structure-activity relationships of this series of agonists are reported. In addition, the pharmacokinetic properties of the most promising compounds are profiled.</description><subject>Amides - chemistry</subject><subject>Amides - pharmacology</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Microsomes, Liver</subject><subject>Miscellaneous</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Pharmacokinetics</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Receptor, Cannabinoid, CB2 - agonists</subject><subject>Structure-Activity Relationship</subject><subject>Sulfones - chemistry</subject><subject>Sulfones - pharmacology</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcFu1DAQhi0EokvhBTggX-DUhBnbcTbcygItUiUkChI3y-tMqJckTjPZlfax-iI8E1m6gmNPc_n-_9foE-IlQo6A9u0mX3ehzRXAMkfMQdlHYoHGmkwbKB6LBVQWsmVlfpyIZ8wbADRgzFNxghVYpUqzELsPkUPa0biXqZG_7zLfxTrxtm1STyw9yyFN1E_S97VkailMcUfS_0x95IkPodV7Jd_J630_3RBHPpPX51_P_vLDjR87H9Kv2NMUgxzGNNA4ReLn4knjW6YXx3sqvn_6-G11mV19ufi8Or_KgrZqyuxah7CGoGs02mAo6rrWoAmV0j54XxchLJuisQa9Kq0lUBUiNVqXhVmWqE_Fm_veefp2Szy5bv6X2tb3lLbsrC1LAFM8CCrQpiiLagbVPRjGxDxS44Yxdn7cOwR30OI27qDFHbQ4RDdrmUOvju3bdUf1_8jRwwy8PgKeg2-b0fch8j9OIei5Tuk_XEaX0g</recordid><startdate>2009</startdate><enddate>2009</enddate><creator>MARX, Isaac E</creator><creator>DIMAURO, Erin F</creator><creator>MARTIN, Matthew W</creator><creator>WHITE, Ryan D</creator><creator>FREMEAU, Robert T</creator><creator>PATEL, Vinod F</creator><creator>CHENG, Alan</creator><creator>EMKEY, Renee</creator><creator>HITCHCOCK, Stephen A</creator><creator>LIYUE HUANG</creator><creator>HUANG, Ming Y</creator><creator>HUMAN, Jason</creator><creator>LEE, Josie H</creator><creator>XINGWEN LI</creator><general>Elsevier</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>2009</creationdate><title>Discovery of α-amidosulfones as potent and selective agonists of CB2 : Synthesis, SAR, and pharmacokinetic properties</title><author>MARX, Isaac E ; DIMAURO, Erin F ; MARTIN, Matthew W ; WHITE, Ryan D ; FREMEAU, Robert T ; PATEL, Vinod F ; CHENG, Alan ; EMKEY, Renee ; HITCHCOCK, Stephen A ; LIYUE HUANG ; HUANG, Ming Y ; HUMAN, Jason ; LEE, Josie H ; XINGWEN LI</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-6b3ccb0c3d14341c5ddd303e1223acaad5cc8f5f641a2766e02911ef337548713</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Amides - chemistry</topic><topic>Amides - pharmacology</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Microsomes, Liver</topic><topic>Miscellaneous</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Pharmacokinetics</topic><topic>Pharmacology. Drug treatments</topic><topic>Rats</topic><topic>Receptor, Cannabinoid, CB2 - agonists</topic><topic>Structure-Activity Relationship</topic><topic>Sulfones - chemistry</topic><topic>Sulfones - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>MARX, Isaac E</creatorcontrib><creatorcontrib>DIMAURO, Erin F</creatorcontrib><creatorcontrib>MARTIN, Matthew W</creatorcontrib><creatorcontrib>WHITE, Ryan D</creatorcontrib><creatorcontrib>FREMEAU, Robert T</creatorcontrib><creatorcontrib>PATEL, Vinod F</creatorcontrib><creatorcontrib>CHENG, Alan</creatorcontrib><creatorcontrib>EMKEY, Renee</creatorcontrib><creatorcontrib>HITCHCOCK, Stephen A</creatorcontrib><creatorcontrib>LIYUE HUANG</creatorcontrib><creatorcontrib>HUANG, Ming Y</creatorcontrib><creatorcontrib>HUMAN, Jason</creatorcontrib><creatorcontrib>LEE, Josie H</creatorcontrib><creatorcontrib>XINGWEN LI</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic &amp; medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>MARX, Isaac E</au><au>DIMAURO, Erin F</au><au>MARTIN, Matthew W</au><au>WHITE, Ryan D</au><au>FREMEAU, Robert T</au><au>PATEL, Vinod F</au><au>CHENG, Alan</au><au>EMKEY, Renee</au><au>HITCHCOCK, Stephen A</au><au>LIYUE HUANG</au><au>HUANG, Ming Y</au><au>HUMAN, Jason</au><au>LEE, Josie H</au><au>XINGWEN LI</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of α-amidosulfones as potent and selective agonists of CB2 : Synthesis, SAR, and pharmacokinetic properties</atitle><jtitle>Bioorganic &amp; medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2009</date><risdate>2009</risdate><volume>19</volume><issue>1</issue><spage>31</spage><epage>35</epage><pages>31-35</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of alpha-amidosulfones were found to be potent and selective agonists of CB(2). The discovery, synthesis, and structure-activity relationships of this series of agonists are reported. In addition, the pharmacokinetic properties of the most promising compounds are profiled.</abstract><cop>Amsterdam</cop><pub>Elsevier</pub><pmid>19062274</pmid><doi>10.1016/j.bmcl.2008.11.026</doi><tpages>5</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0960-894X
ispartof Bioorganic & medicinal chemistry letters, 2009, Vol.19 (1), p.31-35
issn 0960-894X
1464-3405
language eng
recordid cdi_proquest_miscellaneous_66770045
source MEDLINE; Elsevier ScienceDirect Journals
subjects Amides - chemistry
Amides - pharmacology
Animals
Biological and medical sciences
Humans
Medical sciences
Microsomes, Liver
Miscellaneous
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Pharmacokinetics
Pharmacology. Drug treatments
Rats
Receptor, Cannabinoid, CB2 - agonists
Structure-Activity Relationship
Sulfones - chemistry
Sulfones - pharmacology
title Discovery of α-amidosulfones as potent and selective agonists of CB2 : Synthesis, SAR, and pharmacokinetic properties
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-19T00%3A39%3A29IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Discovery%20of%20%CE%B1-amidosulfones%20as%20potent%20and%20selective%20agonists%20of%20CB2%20:%20Synthesis,%20SAR,%20and%20pharmacokinetic%20properties&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry%20letters&rft.au=MARX,%20Isaac%20E&rft.date=2009&rft.volume=19&rft.issue=1&rft.spage=31&rft.epage=35&rft.pages=31-35&rft.issn=0960-894X&rft.eissn=1464-3405&rft_id=info:doi/10.1016/j.bmcl.2008.11.026&rft_dat=%3Cproquest_cross%3E20345759%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=20345759&rft_id=info:pmid/19062274&rfr_iscdi=true