Piperazinyl benzamidines: Synthesis and affinity for the delta opioid receptor
Piperazinyl benzamidines were prepared and found to bind to the rat delta (δ) opioid receptor. The most active compounds had a N,N-diethylcarboxamido group and a N-benzyl piperazine. The most potent among these was N,N-diethyl-4-[4-(phenylmethyl)-1-piperazinyl][2-(trifluoromethyl)phenyl]iminomethyl]...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2001-07, Vol.11 (13), p.1741-1743 |
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| container_end_page | 1743 |
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| container_issue | 13 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 11 |
| creator | Nortey, Samuel O. Baxter, Ellen W. Codd, Ellen E. Zhang, Sui-Po Reitz, Allen B. |
| description | Piperazinyl benzamidines were prepared and found to bind to the rat delta (δ) opioid receptor. The most active compounds had a
N,N-diethylcarboxamido group and a
N-benzyl piperazine. The most potent among these was
N,N-diethyl-4-[4-(phenylmethyl)-1-piperazinyl][2-(trifluoromethyl)phenyl]iminomethyl]benzamide (
27) with a 1.22
nM
K
i for the rat δ opioid receptor and ca. 1000× selectivity relative to the μ opioid subtype.
Piperazinyl benzamides such as
27 are potent and selective δ opioid receptor ligands. |
| doi_str_mv | 10.1016/S0960-894X(01)00272-4 |
| format | Article |
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N,N-diethylcarboxamido group and a
N-benzyl piperazine. The most potent among these was
N,N-diethyl-4-[4-(phenylmethyl)-1-piperazinyl][2-(trifluoromethyl)phenyl]iminomethyl]benzamide (
27) with a 1.22
nM
K
i for the rat δ opioid receptor and ca. 1000× selectivity relative to the μ opioid subtype.
Piperazinyl benzamides such as
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N,N-diethylcarboxamido group and a
N-benzyl piperazine. The most potent among these was
N,N-diethyl-4-[4-(phenylmethyl)-1-piperazinyl][2-(trifluoromethyl)phenyl]iminomethyl]benzamide (
27) with a 1.22
nM
K
i for the rat δ opioid receptor and ca. 1000× selectivity relative to the μ opioid subtype.
Piperazinyl benzamides such as
27 are potent and selective δ opioid receptor ligands.</description><subject>Animals</subject><subject>Benzamidines - chemical synthesis</subject><subject>Benzamidines - chemistry</subject><subject>Benzamidines - metabolism</subject><subject>Biological and medical sciences</subject><subject>Medical sciences</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>Piperazines - chemistry</subject><subject>Rats</subject><subject>Receptors, Opioid, delta - metabolism</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkF1LHDEUhoNU6lb7E5RclNJejD2ZSTJJb0qRtgpiBRW8C5nkBCOzmWkyW1h_vbPu0vauVwcOz_l4H0KOGZwyYPLTDWgJldL8_gOwjwB1W1d8jywYl7xqOIhXZPEHOSBvSnkEYBw4f00OGOO1EAIW5Oo6jpjtU0zrnnaYnuwy-piwfKY36zQ9YImF2uSpDSGmOK1pGDKd-9RjP1k6jHGInmZ0OE5DPiL7wfYF3-7qIbn7_u327Ly6_Pnj4uzrZeUaDVPVSei4UrJDCYjCBqHbpg2aK2lVrecMWintOQpsnW1F6KBttPBKSsaU4M0heb_dO-bh1wrLZJaxOOx7m3BYFdNuotcNzKDYgi4PpWQMZsxxafPaMDAbkeZFpNlYMsDMi0izOXCyO7Dqluj_Tu3MzcC7HWCLs33INrlY_tk-Z2jljH3ZYjjb-B0xm-IiJoc-zs4m44f4n0-eAbqqjyw</recordid><startdate>20010709</startdate><enddate>20010709</enddate><creator>Nortey, Samuel O.</creator><creator>Baxter, Ellen W.</creator><creator>Codd, Ellen E.</creator><creator>Zhang, Sui-Po</creator><creator>Reitz, Allen B.</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>20010709</creationdate><title>Piperazinyl benzamidines: Synthesis and affinity for the delta opioid receptor</title><author>Nortey, Samuel O. ; Baxter, Ellen W. ; Codd, Ellen E. ; Zhang, Sui-Po ; Reitz, Allen B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-b60b4886be60ee5af59737f9486a8291469889d4e5e7ca75fb07395d866118543</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Animals</topic><topic>Benzamidines - chemical synthesis</topic><topic>Benzamidines - chemistry</topic><topic>Benzamidines - metabolism</topic><topic>Biological and medical sciences</topic><topic>Medical sciences</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>Piperazines - chemistry</topic><topic>Rats</topic><topic>Receptors, Opioid, delta - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nortey, Samuel O.</creatorcontrib><creatorcontrib>Baxter, Ellen W.</creatorcontrib><creatorcontrib>Codd, Ellen E.</creatorcontrib><creatorcontrib>Zhang, Sui-Po</creatorcontrib><creatorcontrib>Reitz, Allen B.</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>Nortey, Samuel O.</au><au>Baxter, Ellen W.</au><au>Codd, Ellen E.</au><au>Zhang, Sui-Po</au><au>Reitz, Allen B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Piperazinyl benzamidines: Synthesis and affinity for the delta opioid receptor</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2001-07-09</date><risdate>2001</risdate><volume>11</volume><issue>13</issue><spage>1741</spage><epage>1743</epage><pages>1741-1743</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Piperazinyl benzamidines were prepared and found to bind to the rat delta (δ) opioid receptor. The most active compounds had a
N,N-diethylcarboxamido group and a
N-benzyl piperazine. The most potent among these was
N,N-diethyl-4-[4-(phenylmethyl)-1-piperazinyl][2-(trifluoromethyl)phenyl]iminomethyl]benzamide (
27) with a 1.22
nM
K
i for the rat δ opioid receptor and ca. 1000× selectivity relative to the μ opioid subtype.
Piperazinyl benzamides such as
27 are potent and selective δ opioid receptor ligands.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>11425550</pmid><doi>10.1016/S0960-894X(01)00272-4</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2001-07, Vol.11 (13), p.1741-1743 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_70960230 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Animals Benzamidines - chemical synthesis Benzamidines - chemistry Benzamidines - metabolism Biological and medical sciences Medical sciences Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Piperazines - chemistry Rats Receptors, Opioid, delta - metabolism |
| title | Piperazinyl benzamidines: Synthesis and affinity for the delta opioid receptor |
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