Synthesis and evaluation of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 3: Heterocyclic P3
A series of N α-2-benzoxazolyl-α-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure–activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are di...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2006-04, Vol.16 (7), p.1975-1980 |
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| container_end_page | 1980 |
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| container_issue | 7 |
| container_start_page | 1975 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 16 |
| creator | Tully, David C. Liu, Hong Alper, Phil B. Chatterjee, Arnab K. Epple, Robert Roberts, Michael J. Williams, Jennifer A. Nguyen, KhanhLinh T. Woodmansee, David H. Tumanut, Christine Li, Jun Spraggon, Glen Chang, Jonathan Tuntland, Tove Harris, Jennifer L. Karanewsky, Donald S. |
| description | A series of
N
α-2-benzoxazolyl-α-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure–activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound
3 bound to the active site of cathepsin S is also reported.
A series of
N
α-2-benzoxazolyl-α-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure–activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound
3 bound to the active site of cathepsin S is also reported. |
| doi_str_mv | 10.1016/j.bmcl.2005.12.095 |
| format | Article |
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N
α-2-benzoxazolyl-α-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure–activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound
3 bound to the active site of cathepsin S is also reported.
A series of
N
α-2-benzoxazolyl-α-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure–activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound
3 bound to the active site of cathepsin S is also reported.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2005.12.095</identifier><identifier>PMID: 16446091</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Amides - chemistry ; Amides - pharmacology ; Animals ; Biological and medical sciences ; Cathepsin ; Cathepsin S ; Cathepsins - antagonists & inhibitors ; Cathepsins - chemistry ; Cathepsins - genetics ; Cathepsins - physiology ; Crystallography, X-Ray ; Cysteine protease inhibitor ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Heterocyclic Compounds - chemistry ; Heterocyclic Compounds - pharmacology ; Immunomodulators ; Medical sciences ; Mice ; Mice, Knockout ; Models, Molecular ; Noncovalent inhibitor ; Peptidomimetics ; Pharmacology. Drug treatments ; Rats</subject><ispartof>Bioorganic & medicinal chemistry letters, 2006-04, Vol.16 (7), p.1975-1980</ispartof><rights>2006 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-c966660824772815a648d2a0c6bfba6264fab130b29f016864c1d27ec4fc717c3</citedby><cites>FETCH-LOGICAL-c415t-c966660824772815a648d2a0c6bfba6264fab130b29f016864c1d27ec4fc717c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2005.12.095$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17561120$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16446091$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tully, David C.</creatorcontrib><creatorcontrib>Liu, Hong</creatorcontrib><creatorcontrib>Alper, Phil B.</creatorcontrib><creatorcontrib>Chatterjee, Arnab K.</creatorcontrib><creatorcontrib>Epple, Robert</creatorcontrib><creatorcontrib>Roberts, Michael J.</creatorcontrib><creatorcontrib>Williams, Jennifer A.</creatorcontrib><creatorcontrib>Nguyen, KhanhLinh T.</creatorcontrib><creatorcontrib>Woodmansee, David H.</creatorcontrib><creatorcontrib>Tumanut, Christine</creatorcontrib><creatorcontrib>Li, Jun</creatorcontrib><creatorcontrib>Spraggon, Glen</creatorcontrib><creatorcontrib>Chang, Jonathan</creatorcontrib><creatorcontrib>Tuntland, Tove</creatorcontrib><creatorcontrib>Harris, Jennifer L.</creatorcontrib><creatorcontrib>Karanewsky, Donald S.</creatorcontrib><title>Synthesis and evaluation of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 3: Heterocyclic P3</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of
N
α-2-benzoxazolyl-α-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure–activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound
3 bound to the active site of cathepsin S is also reported.
A series of
N
α-2-benzoxazolyl-α-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure–activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound
3 bound to the active site of cathepsin S is also reported.</description><subject>Amides - chemistry</subject><subject>Amides - pharmacology</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cathepsin</subject><subject>Cathepsin S</subject><subject>Cathepsins - antagonists & inhibitors</subject><subject>Cathepsins - chemistry</subject><subject>Cathepsins - genetics</subject><subject>Cathepsins - physiology</subject><subject>Crystallography, X-Ray</subject><subject>Cysteine protease inhibitor</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Heterocyclic Compounds - pharmacology</subject><subject>Immunomodulators</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Knockout</subject><subject>Models, Molecular</subject><subject>Noncovalent inhibitor</subject><subject>Peptidomimetics</subject><subject>Pharmacology. 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Part 3: Heterocyclic P3</title><author>Tully, David C. ; Liu, Hong ; Alper, Phil B. ; Chatterjee, Arnab K. ; Epple, Robert ; Roberts, Michael J. ; Williams, Jennifer A. ; Nguyen, KhanhLinh T. ; Woodmansee, David H. ; Tumanut, Christine ; Li, Jun ; Spraggon, Glen ; Chang, Jonathan ; Tuntland, Tove ; Harris, Jennifer L. ; Karanewsky, Donald S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-c966660824772815a648d2a0c6bfba6264fab130b29f016864c1d27ec4fc717c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Amides - chemistry</topic><topic>Amides - pharmacology</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cathepsin</topic><topic>Cathepsin S</topic><topic>Cathepsins - antagonists & inhibitors</topic><topic>Cathepsins - chemistry</topic><topic>Cathepsins - genetics</topic><topic>Cathepsins - physiology</topic><topic>Crystallography, X-Ray</topic><topic>Cysteine protease inhibitor</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Heterocyclic Compounds - pharmacology</topic><topic>Immunomodulators</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Mice, Knockout</topic><topic>Models, Molecular</topic><topic>Noncovalent inhibitor</topic><topic>Peptidomimetics</topic><topic>Pharmacology. 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Part 3: Heterocyclic P3</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2006-04-01</date><risdate>2006</risdate><volume>16</volume><issue>7</issue><spage>1975</spage><epage>1980</epage><pages>1975-1980</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of
N
α-2-benzoxazolyl-α-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure–activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound
3 bound to the active site of cathepsin S is also reported.
A series of
N
α-2-benzoxazolyl-α-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure–activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound
3 bound to the active site of cathepsin S is also reported.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16446091</pmid><doi>10.1016/j.bmcl.2005.12.095</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2006-04, Vol.16 (7), p.1975-1980 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67688843 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Amides - chemistry Amides - pharmacology Animals Biological and medical sciences Cathepsin Cathepsin S Cathepsins - antagonists & inhibitors Cathepsins - chemistry Cathepsins - genetics Cathepsins - physiology Crystallography, X-Ray Cysteine protease inhibitor Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Heterocyclic Compounds - chemistry Heterocyclic Compounds - pharmacology Immunomodulators Medical sciences Mice Mice, Knockout Models, Molecular Noncovalent inhibitor Peptidomimetics Pharmacology. Drug treatments Rats |
| title | Synthesis and evaluation of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 3: Heterocyclic P3 |
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