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Structure–activity relationship (SAR) of the α-amino acid residue of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists
Structure–activity relationship (SAR) of the α-amino acid residue and identification of (S)-2,3-diaminopropanoic acid (DAP) replacements of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists are described. This letter describes the structure–activity relationship (SAR) of the ‘rig...
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| Published in: | Bioorganic & medicinal chemistry letters 2011-01, Vol.21 (1), p.307-310 |
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| Main Authors: | , , , , , , , , , , , , , , , , , |
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| cited_by | cdi_FETCH-LOGICAL-c441t-58ac45b0005b08ac9598f991784fe046188cb1f94e62b0f0da89d34bc8833bc53 |
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| cites | cdi_FETCH-LOGICAL-c441t-58ac45b0005b08ac9598f991784fe046188cb1f94e62b0f0da89d34bc8833bc53 |
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| container_issue | 1 |
| container_start_page | 307 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 21 |
| creator | Zhong, Min Hanan, Emily J. Shen, Wang Bui, Minna Arkin, Michelle R. Barr, Kenneth J. Evanchik, Marc J. Hoch, Ute Hyde, Jennifer Martell, Jose R. Oslob, Johan D. Paulvannan, Kumar Prabhu, Saileta Silverman, Jeffrey A. Wright, Jasmin Yu, Chul H. Zhu, Jiang Flanagan, W. Mike |
| description | Structure–activity relationship (SAR) of the α-amino acid residue and identification of (S)-2,3-diaminopropanoic acid (DAP) replacements of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists are described.
This letter describes the structure–activity relationship (SAR) of the ‘right-wing’ α-amino acid residue of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists. Novel (S)-substituted heteroaryl-bearing α-amino acids have been identified as replacements of the ‘right-wing’ (S)-2,3-diaminopropanoic acid (DAP) moiety. Improvement of potency in the Hut-78 assay in the presence of 10% human serum has also been achieved. |
| doi_str_mv | 10.1016/j.bmcl.2010.11.014 |
| format | article |
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This letter describes the structure–activity relationship (SAR) of the ‘right-wing’ α-amino acid residue of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists. Novel (S)-substituted heteroaryl-bearing α-amino acids have been identified as replacements of the ‘right-wing’ (S)-2,3-diaminopropanoic acid (DAP) moiety. Improvement of potency in the Hut-78 assay in the presence of 10% human serum has also been achieved.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2010.11.014</identifier><identifier>PMID: 21109434</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>(S)-2,3-Diaminopropanoic acid replacement ; amino acids ; Amino Acids - chemistry ; Animals ; antagonists ; beta-Alanine - analogs & derivatives ; beta-Alanine - chemistry ; Biological and medical sciences ; blood serum ; Bones, joints and connective tissue. Antiinflammatory agents ; humans ; Immunomodulators ; Intercellular Adhesion Molecule-1 - chemistry ; Intercellular Adhesion Molecule-1 - metabolism ; LFA-1/ICAM-1 antagonist ; Lymphocyte Function-Associated Antigen-1 - chemistry ; Lymphocyte Function-Associated Antigen-1 - metabolism ; Male ; Medical sciences ; Pharmacology. Drug treatments ; Rats ; Rats, Sprague-Dawley ; Structure-Activity Relationship ; structure-activity relationships ; Tetrahydroisoquinoline ; Tetrahydroisoquinolines - chemical synthesis ; Tetrahydroisoquinolines - chemistry ; Tetrahydroisoquinolines - pharmacokinetics ; α-Amino acid</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-01, Vol.21 (1), p.307-310</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c441t-58ac45b0005b08ac9598f991784fe046188cb1f94e62b0f0da89d34bc8833bc53</citedby><cites>FETCH-LOGICAL-c441t-58ac45b0005b08ac9598f991784fe046188cb1f94e62b0f0da89d34bc8833bc53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23726806$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21109434$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhong, Min</creatorcontrib><creatorcontrib>Hanan, Emily J.</creatorcontrib><creatorcontrib>Shen, Wang</creatorcontrib><creatorcontrib>Bui, Minna</creatorcontrib><creatorcontrib>Arkin, Michelle R.</creatorcontrib><creatorcontrib>Barr, Kenneth J.</creatorcontrib><creatorcontrib>Evanchik, Marc J.</creatorcontrib><creatorcontrib>Hoch, Ute</creatorcontrib><creatorcontrib>Hyde, Jennifer</creatorcontrib><creatorcontrib>Martell, Jose R.</creatorcontrib><creatorcontrib>Oslob, Johan D.</creatorcontrib><creatorcontrib>Paulvannan, Kumar</creatorcontrib><creatorcontrib>Prabhu, Saileta</creatorcontrib><creatorcontrib>Silverman, Jeffrey A.</creatorcontrib><creatorcontrib>Wright, Jasmin</creatorcontrib><creatorcontrib>Yu, Chul H.</creatorcontrib><creatorcontrib>Zhu, Jiang</creatorcontrib><creatorcontrib>Flanagan, W. Mike</creatorcontrib><title>Structure–activity relationship (SAR) of the α-amino acid residue of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Structure–activity relationship (SAR) of the α-amino acid residue and identification of (S)-2,3-diaminopropanoic acid (DAP) replacements of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists are described.
This letter describes the structure–activity relationship (SAR) of the ‘right-wing’ α-amino acid residue of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists. Novel (S)-substituted heteroaryl-bearing α-amino acids have been identified as replacements of the ‘right-wing’ (S)-2,3-diaminopropanoic acid (DAP) moiety. Improvement of potency in the Hut-78 assay in the presence of 10% human serum has also been achieved.</description><subject>(S)-2,3-Diaminopropanoic acid replacement</subject><subject>amino acids</subject><subject>Amino Acids - chemistry</subject><subject>Animals</subject><subject>antagonists</subject><subject>beta-Alanine - analogs & derivatives</subject><subject>beta-Alanine - chemistry</subject><subject>Biological and medical sciences</subject><subject>blood serum</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>humans</subject><subject>Immunomodulators</subject><subject>Intercellular Adhesion Molecule-1 - chemistry</subject><subject>Intercellular Adhesion Molecule-1 - metabolism</subject><subject>LFA-1/ICAM-1 antagonist</subject><subject>Lymphocyte Function-Associated Antigen-1 - chemistry</subject><subject>Lymphocyte Function-Associated Antigen-1 - metabolism</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>Structure-Activity Relationship</subject><subject>structure-activity relationships</subject><subject>Tetrahydroisoquinoline</subject><subject>Tetrahydroisoquinolines - chemical synthesis</subject><subject>Tetrahydroisoquinolines - chemistry</subject><subject>Tetrahydroisoquinolines - pharmacokinetics</subject><subject>α-Amino acid</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqF0cFu0zAYB3ALgVgZvAAH8AWxHdLZiZPaEpdq2tikIgTdJG6WY39ZXSVxZzuVetsLcOJJeBEegifBUQvc4GJb9u-zP_mP0EtKppTQ6mw9rTvdTnMybtApoewRmlBWsaxgpHyMJkRUJOOCfTlCz0JYkyQIY0_RUU4pEaxgE_R1Gf2g4-Dh58M3paPd2rjDHloVrevDym7wyXL--RS7BscV4B_fM9XZ3mGlrUkuWDPAeLhxEfqII0SvVjvjnQ3ufkiytT3gk5ur60-nmQFvt2Dw4nKe0bPr8_mHjGLVR3XnehtieI6eNKoN8OIwH6Pby4ub86ts8fF90otMM0ZjVnKlWVkTQtKQ1qIUvBGCzjhrgLCKcq5r2ggGVV6ThhjFhSlYrTkvilqXxTF6u79341OTEKLsbNDQtqoHNwSZHMl5Vc3-L9NXCp4LkWS-l9q7EDw0cuNtp_xOUiLHvORajnnJMS9JqUxppKJXh-uHugPzp-R3QAm8OQAVtGobr3ptw19XzPKKkyq513vXKCfVnU_mdpleKlPoBcsZSeLdXkD62K0FL4O20Gsw1oOO0jj7r05_ASPpvec</recordid><startdate>20110101</startdate><enddate>20110101</enddate><creator>Zhong, Min</creator><creator>Hanan, Emily J.</creator><creator>Shen, Wang</creator><creator>Bui, Minna</creator><creator>Arkin, Michelle R.</creator><creator>Barr, Kenneth J.</creator><creator>Evanchik, Marc J.</creator><creator>Hoch, Ute</creator><creator>Hyde, Jennifer</creator><creator>Martell, Jose R.</creator><creator>Oslob, Johan D.</creator><creator>Paulvannan, Kumar</creator><creator>Prabhu, Saileta</creator><creator>Silverman, Jeffrey A.</creator><creator>Wright, Jasmin</creator><creator>Yu, Chul H.</creator><creator>Zhu, Jiang</creator><creator>Flanagan, W. 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Antiinflammatory agents</topic><topic>humans</topic><topic>Immunomodulators</topic><topic>Intercellular Adhesion Molecule-1 - chemistry</topic><topic>Intercellular Adhesion Molecule-1 - metabolism</topic><topic>LFA-1/ICAM-1 antagonist</topic><topic>Lymphocyte Function-Associated Antigen-1 - chemistry</topic><topic>Lymphocyte Function-Associated Antigen-1 - metabolism</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>Structure-Activity Relationship</topic><topic>structure-activity relationships</topic><topic>Tetrahydroisoquinoline</topic><topic>Tetrahydroisoquinolines - chemical synthesis</topic><topic>Tetrahydroisoquinolines - chemistry</topic><topic>Tetrahydroisoquinolines - pharmacokinetics</topic><topic>α-Amino acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhong, Min</creatorcontrib><creatorcontrib>Hanan, Emily J.</creatorcontrib><creatorcontrib>Shen, Wang</creatorcontrib><creatorcontrib>Bui, Minna</creatorcontrib><creatorcontrib>Arkin, Michelle R.</creatorcontrib><creatorcontrib>Barr, Kenneth J.</creatorcontrib><creatorcontrib>Evanchik, Marc J.</creatorcontrib><creatorcontrib>Hoch, Ute</creatorcontrib><creatorcontrib>Hyde, Jennifer</creatorcontrib><creatorcontrib>Martell, Jose R.</creatorcontrib><creatorcontrib>Oslob, Johan D.</creatorcontrib><creatorcontrib>Paulvannan, Kumar</creatorcontrib><creatorcontrib>Prabhu, Saileta</creatorcontrib><creatorcontrib>Silverman, Jeffrey A.</creatorcontrib><creatorcontrib>Wright, Jasmin</creatorcontrib><creatorcontrib>Yu, Chul H.</creatorcontrib><creatorcontrib>Zhu, Jiang</creatorcontrib><creatorcontrib>Flanagan, W. 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Mike</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure–activity relationship (SAR) of the α-amino acid residue of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2011-01-01</date><risdate>2011</risdate><volume>21</volume><issue>1</issue><spage>307</spage><epage>310</epage><pages>307-310</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Structure–activity relationship (SAR) of the α-amino acid residue and identification of (S)-2,3-diaminopropanoic acid (DAP) replacements of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists are described.
This letter describes the structure–activity relationship (SAR) of the ‘right-wing’ α-amino acid residue of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists. Novel (S)-substituted heteroaryl-bearing α-amino acids have been identified as replacements of the ‘right-wing’ (S)-2,3-diaminopropanoic acid (DAP) moiety. Improvement of potency in the Hut-78 assay in the presence of 10% human serum has also been achieved.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21109434</pmid><doi>10.1016/j.bmcl.2010.11.014</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2011-01, Vol.21 (1), p.307-310 |
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| subjects | (S)-2,3-Diaminopropanoic acid replacement amino acids Amino Acids - chemistry Animals antagonists beta-Alanine - analogs & derivatives beta-Alanine - chemistry Biological and medical sciences blood serum Bones, joints and connective tissue. Antiinflammatory agents humans Immunomodulators Intercellular Adhesion Molecule-1 - chemistry Intercellular Adhesion Molecule-1 - metabolism LFA-1/ICAM-1 antagonist Lymphocyte Function-Associated Antigen-1 - chemistry Lymphocyte Function-Associated Antigen-1 - metabolism Male Medical sciences Pharmacology. Drug treatments Rats Rats, Sprague-Dawley Structure-Activity Relationship structure-activity relationships Tetrahydroisoquinoline Tetrahydroisoquinolines - chemical synthesis Tetrahydroisoquinolines - chemistry Tetrahydroisoquinolines - pharmacokinetics α-Amino acid |
| title | Structure–activity relationship (SAR) of the α-amino acid residue of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists |
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