Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2)
[Display omitted] Salvinorin A is the only known non-nitrogenous and specific κ-opioid agonist. A series of salvinorin A derivatives were prepared and tested for in vitro activity at the κ-opioid receptor. Unsubstituted carbamate 9 was a potent κ-agonist (EC 50 = 6.2 nM) and should be more stable th...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2005-06, Vol.15 (11), p.2761-2765 |
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| container_issue | 11 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 15 |
| creator | Béguin, Cécile Richards, Michele R. Wang, Yulin Chen, Yong Liu-Chen, Lee-Yuan Ma, Zhongze Lee, David Y.W. Carlezon, William A. Cohen, Bruce M. |
| description | [Display omitted]
Salvinorin A is the only known non-nitrogenous and specific κ-opioid agonist. A series of salvinorin A derivatives were prepared and tested for in vitro activity at the κ-opioid receptor. Unsubstituted carbamate
9 was a potent κ-agonist (EC
50
=
6.2
nM) and should be more stable than salvinorin A toward metabolic transformations. Compound
10, containing an
N-methyl carbamate at C(2), showed partial agonist activity with 81% efficacy when compared with the full agonist U50,488H. No antagonist ligands were observed. |
| doi_str_mv | 10.1016/j.bmcl.2005.03.113 |
| format | Article |
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Salvinorin A is the only known non-nitrogenous and specific κ-opioid agonist. A series of salvinorin A derivatives were prepared and tested for in vitro activity at the κ-opioid receptor. Unsubstituted carbamate
9 was a potent κ-agonist (EC
50
=
6.2
nM) and should be more stable than salvinorin A toward metabolic transformations. Compound
10, containing an
N-methyl carbamate at C(2), showed partial agonist activity with 81% efficacy when compared with the full agonist U50,488H. No antagonist ligands were observed.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2005.03.113</identifier><identifier>PMID: 15869877</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Agonist ; Animals ; Biological and medical sciences ; CHO Cells ; Cricetinae ; Diterpenes - chemical synthesis ; Diterpenes - chemistry ; Diterpenes - pharmacology ; Diterpenes, Clerodane ; Drug Evaluation, Preclinical ; Kappa-opioid receptor ; Medical sciences ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Partial agonist ; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems ; Pharmacology. Drug treatments ; Salvinorin ; Structure–activity relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2005-06, Vol.15 (11), p.2761-2765</ispartof><rights>2005 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c384t-deb44f95cd12aabdabb934a7dc7976496d1ce5daa8e6465338c2115aceef678a3</citedby><cites>FETCH-LOGICAL-c384t-deb44f95cd12aabdabb934a7dc7976496d1ce5daa8e6465338c2115aceef678a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X05004361$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16810661$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15869877$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Béguin, Cécile</creatorcontrib><creatorcontrib>Richards, Michele R.</creatorcontrib><creatorcontrib>Wang, Yulin</creatorcontrib><creatorcontrib>Chen, Yong</creatorcontrib><creatorcontrib>Liu-Chen, Lee-Yuan</creatorcontrib><creatorcontrib>Ma, Zhongze</creatorcontrib><creatorcontrib>Lee, David Y.W.</creatorcontrib><creatorcontrib>Carlezon, William A.</creatorcontrib><creatorcontrib>Cohen, Bruce M.</creatorcontrib><title>Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2)</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
Salvinorin A is the only known non-nitrogenous and specific κ-opioid agonist. A series of salvinorin A derivatives were prepared and tested for in vitro activity at the κ-opioid receptor. Unsubstituted carbamate
9 was a potent κ-agonist (EC
50
=
6.2
nM) and should be more stable than salvinorin A toward metabolic transformations. Compound
10, containing an
N-methyl carbamate at C(2), showed partial agonist activity with 81% efficacy when compared with the full agonist U50,488H. No antagonist ligands were observed.</description><subject>Agonist</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>CHO Cells</subject><subject>Cricetinae</subject><subject>Diterpenes - chemical synthesis</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - pharmacology</subject><subject>Diterpenes, Clerodane</subject><subject>Drug Evaluation, Preclinical</subject><subject>Kappa-opioid receptor</subject><subject>Medical sciences</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Partial agonist</subject><subject>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</subject><subject>Pharmacology. Drug treatments</subject><subject>Salvinorin</subject><subject>Structure–activity relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp90MFq3DAQgGFRErrbbV-gh6BLSnOwI1mybEMvYWmTQCCHJJBDQYylcaPFtjaSvZC3r5ZdyC2nuXwzDD8h3znLOePqcpO3g-nzgrEyZyLnXHwiSy6VzIRk5QlZskaxrG7k84J8iXHDGJdMys9kwctaNXVVLcnfh7dxesHoIoXRUjfSnZuCp9sXCAMY3_t_zkBPcQf9DJPzI_UdjdDv3OhD4ldpD5KaMdLBW9c5tBQmuv5ZXHwlpx30Eb8d54o8_fn9uL7J7u6vb9dXd5kRtZwyi62UXVMaywuA1kLbNkJCZU3VVEo2ynKDpQWoUUlVClGbgvMSDGKnqhrEivw43N0G_5oemfTgosG-hxH9HHVCZcFUkWBxgCb4GAN2ehvcAOFNc6b3TfVG75vqfVPNhE5N09LZ8frcDmjfV44REzg_AoipVRdgNC6-O1VzphRP7tfBYWqxcxh0NA5Hg9YFNJO23n30x38qGZYi</recordid><startdate>20050602</startdate><enddate>20050602</enddate><creator>Béguin, Cécile</creator><creator>Richards, Michele R.</creator><creator>Wang, Yulin</creator><creator>Chen, Yong</creator><creator>Liu-Chen, Lee-Yuan</creator><creator>Ma, Zhongze</creator><creator>Lee, David Y.W.</creator><creator>Carlezon, William A.</creator><creator>Cohen, Bruce M.</creator><general>Elsevier Ltd</general><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>7X8</scope></search><sort><creationdate>20050602</creationdate><title>Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2)</title><author>Béguin, Cécile ; Richards, Michele R. ; Wang, Yulin ; Chen, Yong ; Liu-Chen, Lee-Yuan ; Ma, Zhongze ; Lee, David Y.W. ; Carlezon, William A. ; Cohen, Bruce M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c384t-deb44f95cd12aabdabb934a7dc7976496d1ce5daa8e6465338c2115aceef678a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Agonist</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>CHO Cells</topic><topic>Cricetinae</topic><topic>Diterpenes - chemical synthesis</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - pharmacology</topic><topic>Diterpenes, Clerodane</topic><topic>Drug Evaluation, Preclinical</topic><topic>Kappa-opioid receptor</topic><topic>Medical sciences</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Partial agonist</topic><topic>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</topic><topic>Pharmacology. Drug treatments</topic><topic>Salvinorin</topic><topic>Structure–activity relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Béguin, Cécile</creatorcontrib><creatorcontrib>Richards, Michele R.</creatorcontrib><creatorcontrib>Wang, Yulin</creatorcontrib><creatorcontrib>Chen, Yong</creatorcontrib><creatorcontrib>Liu-Chen, Lee-Yuan</creatorcontrib><creatorcontrib>Ma, Zhongze</creatorcontrib><creatorcontrib>Lee, David Y.W.</creatorcontrib><creatorcontrib>Carlezon, William A.</creatorcontrib><creatorcontrib>Cohen, Bruce M.</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Béguin, Cécile</au><au>Richards, Michele R.</au><au>Wang, Yulin</au><au>Chen, Yong</au><au>Liu-Chen, Lee-Yuan</au><au>Ma, Zhongze</au><au>Lee, David Y.W.</au><au>Carlezon, William A.</au><au>Cohen, Bruce M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2)</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2005-06-02</date><risdate>2005</risdate><volume>15</volume><issue>11</issue><spage>2761</spage><epage>2765</epage><pages>2761-2765</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
Salvinorin A is the only known non-nitrogenous and specific κ-opioid agonist. A series of salvinorin A derivatives were prepared and tested for in vitro activity at the κ-opioid receptor. Unsubstituted carbamate
9 was a potent κ-agonist (EC
50
=
6.2
nM) and should be more stable than salvinorin A toward metabolic transformations. Compound
10, containing an
N-methyl carbamate at C(2), showed partial agonist activity with 81% efficacy when compared with the full agonist U50,488H. No antagonist ligands were observed.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15869877</pmid><doi>10.1016/j.bmcl.2005.03.113</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2005-06, Vol.15 (11), p.2761-2765 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Agonist Animals Biological and medical sciences CHO Cells Cricetinae Diterpenes - chemical synthesis Diterpenes - chemistry Diterpenes - pharmacology Diterpenes, Clerodane Drug Evaluation, Preclinical Kappa-opioid receptor Medical sciences Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Partial agonist Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Salvinorin Structure–activity relationship |
| title | Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2) |
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