Synthesis of novel substituted 2-phenylpyrazolopyridines with potent activity against herpesviruses
Herpesviruses are a significant source of human disease; amongst these herpes simplex virus 1 (HSV-1) and HSV-2 are very prevalent and cause recurrent infections. We recently identified a pyrazolo[1,5- a]pyridine scaffold that showed promising activity against HSV-1 and HSV-2 in Vero cell antiviral...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2005-09, Vol.13 (18), p.5346-5361 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Gudmundsson, Kristjan S. Johns, Brian A. Wang, Zhicheng Turner, Elizabeth M. Allen, Scott H. Freeman, George A. Boyd, F. Leslie Sexton, Connie J. Selleseth, Dean W. Moniri, Kelly R. Creech, Katrina L. |
| description | Herpesviruses are a significant source of human disease; amongst these herpes simplex virus 1 (HSV-1) and HSV-2 are very prevalent and cause recurrent infections. We recently identified a pyrazolo[1,5-
a]pyridine scaffold that showed promising activity against HSV-1 and HSV-2 in Vero cell antiviral assays. Here, we describe the synthesis and anti-herpetic activity of several 3-pyrimidinyl-2-phenylpyrazolo[1,5-
a]pyridines with differing 2-phenyl substitution patterns. Approaches to rapidly access a number of analogs with different 2-phenyl substitution patterns are outlined. Several of the compounds described have comparable activity to acyclovir against HSV-1 and HSV-2. |
| doi_str_mv | 10.1016/j.bmc.2005.05.043 |
| format | Article |
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a]pyridine scaffold that showed promising activity against HSV-1 and HSV-2 in Vero cell antiviral assays. Here, we describe the synthesis and anti-herpetic activity of several 3-pyrimidinyl-2-phenylpyrazolo[1,5-
a]pyridines with differing 2-phenyl substitution patterns. Approaches to rapidly access a number of analogs with different 2-phenyl substitution patterns are outlined. Several of the compounds described have comparable activity to acyclovir against HSV-1 and HSV-2.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2005.05.043</identifier><identifier>PMID: 16039862</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Anti-viral compounds ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Biological and medical sciences ; Cell Line ; Cercopithecus aethiops ; Herpesvirus 1, Human - drug effects ; Herpesvirus 2, Human - drug effects ; Herpesviruses ; Humans ; Medical sciences ; Microbial Sensitivity Tests ; Pharmacology. Drug treatments ; Phenol - chemistry ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; Pyrazolopyridines ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Pyridines - pharmacology ; Structure-Activity Relationship ; Vero Cells ; Virus Replication - drug effects</subject><ispartof>Bioorganic & medicinal chemistry, 2005-09, Vol.13 (18), p.5346-5361</ispartof><rights>2005 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-58fe274d3b0fa91f8a619c00fca7e90ed3be819bbc6daf43831b1e2effeb5343</citedby><cites>FETCH-LOGICAL-c381t-58fe274d3b0fa91f8a619c00fca7e90ed3be819bbc6daf43831b1e2effeb5343</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2005.05.043$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17015905$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16039862$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gudmundsson, Kristjan S.</creatorcontrib><creatorcontrib>Johns, Brian A.</creatorcontrib><creatorcontrib>Wang, Zhicheng</creatorcontrib><creatorcontrib>Turner, Elizabeth M.</creatorcontrib><creatorcontrib>Allen, Scott H.</creatorcontrib><creatorcontrib>Freeman, George A.</creatorcontrib><creatorcontrib>Boyd, F. Leslie</creatorcontrib><creatorcontrib>Sexton, Connie J.</creatorcontrib><creatorcontrib>Selleseth, Dean W.</creatorcontrib><creatorcontrib>Moniri, Kelly R.</creatorcontrib><creatorcontrib>Creech, Katrina L.</creatorcontrib><title>Synthesis of novel substituted 2-phenylpyrazolopyridines with potent activity against herpesviruses</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Herpesviruses are a significant source of human disease; amongst these herpes simplex virus 1 (HSV-1) and HSV-2 are very prevalent and cause recurrent infections. We recently identified a pyrazolo[1,5-
a]pyridine scaffold that showed promising activity against HSV-1 and HSV-2 in Vero cell antiviral assays. Here, we describe the synthesis and anti-herpetic activity of several 3-pyrimidinyl-2-phenylpyrazolo[1,5-
a]pyridines with differing 2-phenyl substitution patterns. Approaches to rapidly access a number of analogs with different 2-phenyl substitution patterns are outlined. Several of the compounds described have comparable activity to acyclovir against HSV-1 and HSV-2.</description><subject>Animals</subject><subject>Anti-viral compounds</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>Cercopithecus aethiops</subject><subject>Herpesvirus 1, Human - drug effects</subject><subject>Herpesvirus 2, Human - drug effects</subject><subject>Herpesviruses</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Pharmacology. Drug treatments</subject><subject>Phenol - chemistry</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacology</subject><subject>Pyrazolopyridines</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Pyridines - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Vero Cells</subject><subject>Virus Replication - drug effects</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1r3DAQhkVpaLZJf0AvxZf25o1kybJETyX0CwI9NHchy6OuFq_kauQN7q-Pl13IrfDCHOaZl-Eh5D2jW0aZvNtv-4PbNpS221MEf0U2TEhRc67Za7KhWqqaKi2vyVvEPaW0EZq9IddMUq6VbDbE_V5i2QEGrJKvYjrCWOHcYwllLjBUTT3tIC7jtGT7L41pnWEIEbB6CmVXTalALJV1JRxDWSr7x4aIpdpBngCPIc8IeEuuvB0R3l3mDXn89vXx_kf98Ov7z_svD7XjipW6VR6aTgy8p95q5pWVTDtKvbMdaArrAhTTfe_kYL3girOeQQPeQ99ywW_Ip3PtlNPfGbCYQ0AH42gjpBmNVKLjvNMryM6gywkxgzdTDgebF8OoOYk1e7OKNSex5hTB15sPl_K5P8DwcnExuQIfL4BFZ0efbXQBX7iOslbTduU-nzlYTRwDZIMuQHQwhAyumCGF_7zxDMeymc8</recordid><startdate>20050915</startdate><enddate>20050915</enddate><creator>Gudmundsson, Kristjan S.</creator><creator>Johns, Brian A.</creator><creator>Wang, Zhicheng</creator><creator>Turner, Elizabeth M.</creator><creator>Allen, Scott H.</creator><creator>Freeman, George A.</creator><creator>Boyd, F. Leslie</creator><creator>Sexton, Connie J.</creator><creator>Selleseth, Dean W.</creator><creator>Moniri, Kelly R.</creator><creator>Creech, Katrina L.</creator><general>Elsevier Ltd</general><general>Elsevier Science</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>20050915</creationdate><title>Synthesis of novel substituted 2-phenylpyrazolopyridines with potent activity against herpesviruses</title><author>Gudmundsson, Kristjan S. ; Johns, Brian A. ; Wang, Zhicheng ; Turner, Elizabeth M. ; Allen, Scott H. ; Freeman, George A. ; Boyd, F. Leslie ; Sexton, Connie J. ; Selleseth, Dean W. ; Moniri, Kelly R. ; Creech, Katrina L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-58fe274d3b0fa91f8a619c00fca7e90ed3be819bbc6daf43831b1e2effeb5343</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Animals</topic><topic>Anti-viral compounds</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>Cercopithecus aethiops</topic><topic>Herpesvirus 1, Human - drug effects</topic><topic>Herpesvirus 2, Human - drug effects</topic><topic>Herpesviruses</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Pharmacology. Drug treatments</topic><topic>Phenol - chemistry</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacology</topic><topic>Pyrazolopyridines</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Pyridines - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Vero Cells</topic><topic>Virus Replication - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gudmundsson, Kristjan S.</creatorcontrib><creatorcontrib>Johns, Brian A.</creatorcontrib><creatorcontrib>Wang, Zhicheng</creatorcontrib><creatorcontrib>Turner, Elizabeth M.</creatorcontrib><creatorcontrib>Allen, Scott H.</creatorcontrib><creatorcontrib>Freeman, George A.</creatorcontrib><creatorcontrib>Boyd, F. Leslie</creatorcontrib><creatorcontrib>Sexton, Connie J.</creatorcontrib><creatorcontrib>Selleseth, Dean W.</creatorcontrib><creatorcontrib>Moniri, Kelly R.</creatorcontrib><creatorcontrib>Creech, Katrina L.</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</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gudmundsson, Kristjan S.</au><au>Johns, Brian A.</au><au>Wang, Zhicheng</au><au>Turner, Elizabeth M.</au><au>Allen, Scott H.</au><au>Freeman, George A.</au><au>Boyd, F. Leslie</au><au>Sexton, Connie J.</au><au>Selleseth, Dean W.</au><au>Moniri, Kelly R.</au><au>Creech, Katrina L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of novel substituted 2-phenylpyrazolopyridines with potent activity against herpesviruses</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2005-09-15</date><risdate>2005</risdate><volume>13</volume><issue>18</issue><spage>5346</spage><epage>5361</epage><pages>5346-5361</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Herpesviruses are a significant source of human disease; amongst these herpes simplex virus 1 (HSV-1) and HSV-2 are very prevalent and cause recurrent infections. We recently identified a pyrazolo[1,5-
a]pyridine scaffold that showed promising activity against HSV-1 and HSV-2 in Vero cell antiviral assays. Here, we describe the synthesis and anti-herpetic activity of several 3-pyrimidinyl-2-phenylpyrazolo[1,5-
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| subjects | Animals Anti-viral compounds Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Biological and medical sciences Cell Line Cercopithecus aethiops Herpesvirus 1, Human - drug effects Herpesvirus 2, Human - drug effects Herpesviruses Humans Medical sciences Microbial Sensitivity Tests Pharmacology. Drug treatments Phenol - chemistry Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Pyrazolopyridines Pyridines - chemical synthesis Pyridines - chemistry Pyridines - pharmacology Structure-Activity Relationship Vero Cells Virus Replication - drug effects |
| title | Synthesis of novel substituted 2-phenylpyrazolopyridines with potent activity against herpesviruses |
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