Substituted Indole-5-carboxamides and -acetamides as Potent Nonpeptide GnRH Receptor Antagonists
The 2-aryltryptamine class of GnRH receptor antagonists has been modified to incorporate carboxamide and acetamide substituents at the indole 5-position. With either a phenol or methanesulfonamide terminus on the N-aralkyl side chain, potent binding affinity to the GnRH receptor was achieved. A func...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2001-07, Vol.11 (13), p.1723-1726 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Ashton, Wallace T. Sisco, Rosemary M. Yang, Yi Tien Lo, Jane-Ling Yudkovitz, Joel B. Cheng, Kang Goulet, Mark T. |
| description | The 2-aryltryptamine class of GnRH receptor antagonists has been modified to incorporate carboxamide and acetamide substituents at the indole 5-position. With either a phenol or methanesulfonamide terminus on the
N-aralkyl side chain, potent binding affinity to the GnRH receptor was achieved. A functional assay for GnRH antagonism was even more sensitive to structural modification and revealed a strong preference for branched tertiary amides.
The 2-aryltryptamine class of GnRH receptor antagonists has been modified to incorporate carboxamide and acetamide substituents at the indole 5-position. With either a phenol or methanesulfonamide terminus on the
N-aralkyl side chain, potent binding affinity to the GnRH receptor was achieved. A functional assay for GnRH antagonism was even more sensitive to structural modification and revealed a strong preference fro branched chain amides such as
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45. |
| doi_str_mv | 10.1016/S0960-894X(01)00274-8 |
| format | Article |
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N-aralkyl side chain, potent binding affinity to the GnRH receptor was achieved. A functional assay for GnRH antagonism was even more sensitive to structural modification and revealed a strong preference for branched tertiary amides.
The 2-aryltryptamine class of GnRH receptor antagonists has been modified to incorporate carboxamide and acetamide substituents at the indole 5-position. With either a phenol or methanesulfonamide terminus on the
N-aralkyl side chain, potent binding affinity to the GnRH receptor was achieved. A functional assay for GnRH antagonism was even more sensitive to structural modification and revealed a strong preference fro branched chain amides such as
28 and
45.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(01)00274-8</identifier><identifier>PMID: 11425546</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Amides - chemistry ; Biological and medical sciences ; Hormones. Endocrine system ; Indoles - chemistry ; Indoles - metabolism ; Indoles - pharmacology ; Medical sciences ; Pharmacology. Drug treatments ; Protein Binding ; Receptors, LHRH - antagonists & inhibitors ; Receptors, LHRH - metabolism</subject><ispartof>Bioorganic & medicinal chemistry letters, 2001-07, Vol.11 (13), p.1723-1726</ispartof><rights>2001 Elsevier Science Ltd</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-1ced7e1a6687df46a15be782b8b3bbc43d6f83ed4902114eeca4f2199d09f66a3</citedby><cites>FETCH-LOGICAL-c390t-1ced7e1a6687df46a15be782b8b3bbc43d6f83ed4902114eeca4f2199d09f66a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0960-894X(01)00274-8$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3541,27915,27916,45986</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1046904$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11425546$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ashton, Wallace T.</creatorcontrib><creatorcontrib>Sisco, Rosemary M.</creatorcontrib><creatorcontrib>Yang, Yi Tien</creatorcontrib><creatorcontrib>Lo, Jane-Ling</creatorcontrib><creatorcontrib>Yudkovitz, Joel B.</creatorcontrib><creatorcontrib>Cheng, Kang</creatorcontrib><creatorcontrib>Goulet, Mark T.</creatorcontrib><title>Substituted Indole-5-carboxamides and -acetamides as Potent Nonpeptide GnRH Receptor Antagonists</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The 2-aryltryptamine class of GnRH receptor antagonists has been modified to incorporate carboxamide and acetamide substituents at the indole 5-position. With either a phenol or methanesulfonamide terminus on the
N-aralkyl side chain, potent binding affinity to the GnRH receptor was achieved. A functional assay for GnRH antagonism was even more sensitive to structural modification and revealed a strong preference for branched tertiary amides.
The 2-aryltryptamine class of GnRH receptor antagonists has been modified to incorporate carboxamide and acetamide substituents at the indole 5-position. With either a phenol or methanesulfonamide terminus on the
N-aralkyl side chain, potent binding affinity to the GnRH receptor was achieved. A functional assay for GnRH antagonism was even more sensitive to structural modification and revealed a strong preference fro branched chain amides such as
28 and
45.</description><subject>Amides - chemistry</subject><subject>Biological and medical sciences</subject><subject>Hormones. Endocrine system</subject><subject>Indoles - chemistry</subject><subject>Indoles - metabolism</subject><subject>Indoles - pharmacology</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Protein Binding</subject><subject>Receptors, LHRH - antagonists & inhibitors</subject><subject>Receptors, LHRH - 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>eNqFkEtv1DAQgC1E1W4fPwGUA0JwMB0njhOfUFXRh1QV1IfEzTj2BBll7a3tVO2_x-0ulBun0Yy-eX2EvGHwiQETh9cgBdBe8u8fgH0EqDtO-1dkwbjgtOHQviaLv8gO2U3pFwDjwPk22WGM123LxYL8uJ6HlF2eM9rq3NswIW2p0XEID3rpLKZKe1tRbTD_yVP1LWT0uboMfoWrXKrVqb86q67QlDTE6shn_TN4l3LaJ1ujnhIebOIeuT35cnN8Ri--np4fH11Q00jIlBm0HTItRN_ZkQvN2gG7vh76oRkGwxsrxr5ByyXU5XpEo_lYMyktyFEI3eyR9-u5qxjuZkxZLV0yOE3aY5iT6kC2fbFUwHYNmhhSijiqVXRLHR8VA_WkVj2rVU_eFDD1rFb1pe_tZsE8LNG-dG1cFuDdBtDJ6GmM2huX_pnOhQResM9rDIuNe4dRJePQl_9dRJOVDe4_l_wGV3yWqg</recordid><startdate>20010709</startdate><enddate>20010709</enddate><creator>Ashton, Wallace T.</creator><creator>Sisco, Rosemary M.</creator><creator>Yang, Yi Tien</creator><creator>Lo, Jane-Ling</creator><creator>Yudkovitz, Joel B.</creator><creator>Cheng, Kang</creator><creator>Goulet, Mark T.</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>Substituted Indole-5-carboxamides and -acetamides as Potent Nonpeptide GnRH Receptor Antagonists</title><author>Ashton, Wallace T. ; Sisco, Rosemary M. ; Yang, Yi Tien ; Lo, Jane-Ling ; Yudkovitz, Joel B. ; Cheng, Kang ; Goulet, Mark T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-1ced7e1a6687df46a15be782b8b3bbc43d6f83ed4902114eeca4f2199d09f66a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Amides - chemistry</topic><topic>Biological and medical sciences</topic><topic>Hormones. Endocrine system</topic><topic>Indoles - chemistry</topic><topic>Indoles - metabolism</topic><topic>Indoles - pharmacology</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Protein Binding</topic><topic>Receptors, LHRH - antagonists & inhibitors</topic><topic>Receptors, LHRH - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ashton, Wallace T.</creatorcontrib><creatorcontrib>Sisco, Rosemary M.</creatorcontrib><creatorcontrib>Yang, Yi Tien</creatorcontrib><creatorcontrib>Lo, Jane-Ling</creatorcontrib><creatorcontrib>Yudkovitz, Joel B.</creatorcontrib><creatorcontrib>Cheng, Kang</creatorcontrib><creatorcontrib>Goulet, Mark T.</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>Ashton, Wallace T.</au><au>Sisco, Rosemary M.</au><au>Yang, Yi Tien</au><au>Lo, Jane-Ling</au><au>Yudkovitz, Joel B.</au><au>Cheng, Kang</au><au>Goulet, Mark T.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Substituted Indole-5-carboxamides and -acetamides as Potent Nonpeptide GnRH Receptor Antagonists</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>1723</spage><epage>1726</epage><pages>1723-1726</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The 2-aryltryptamine class of GnRH receptor antagonists has been modified to incorporate carboxamide and acetamide substituents at the indole 5-position. With either a phenol or methanesulfonamide terminus on the
N-aralkyl side chain, potent binding affinity to the GnRH receptor was achieved. A functional assay for GnRH antagonism was even more sensitive to structural modification and revealed a strong preference for branched tertiary amides.
The 2-aryltryptamine class of GnRH receptor antagonists has been modified to incorporate carboxamide and acetamide substituents at the indole 5-position. With either a phenol or methanesulfonamide terminus on the
N-aralkyl side chain, potent binding affinity to the GnRH receptor was achieved. A functional assay for GnRH antagonism was even more sensitive to structural modification and revealed a strong preference fro branched chain amides such as
28 and
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| ispartof | Bioorganic & medicinal chemistry letters, 2001-07, Vol.11 (13), p.1723-1726 |
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| source | Elsevier ScienceDirect Journals Complete - AutoHoldings; MEDLINE |
| subjects | Amides - chemistry Biological and medical sciences Hormones. Endocrine system Indoles - chemistry Indoles - metabolism Indoles - pharmacology Medical sciences Pharmacology. Drug treatments Protein Binding Receptors, LHRH - antagonists & inhibitors Receptors, LHRH - metabolism |
| title | Substituted Indole-5-carboxamides and -acetamides as Potent Nonpeptide GnRH Receptor Antagonists |
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