Synthesis and evaluation of pyrazolone compounds as SARS-coronavirus 3C-like protease inhibitors
A series of pyrazolone compounds as possible SARS-CoV 3CL protease inhibitors were designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide in which several showed potent inhibition against the 3CL protease. Interestingly, one of the inhibitors was also act...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2010-11, Vol.18 (22), p.7849-7854 |
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| creator | Ramajayam, R. Tan, Kian-Pin Liu, Hun-Ge Liang, Po-Huang |
| description | A series of pyrazolone compounds as possible SARS-CoV 3CL protease inhibitors were designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide in which several showed potent inhibition against the 3CL protease. Interestingly, one of the inhibitors was also active against 3C protease from coxsackievirus B3. These inhibitors could be potentially developed into anti-coronaviral and anti-picornaviral agents.
A series of pyrazolone compounds as possible SARS-CoV 3CL protease inhibitors were designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide in which several showed potent inhibition against the 3CL protease. Interestingly, one of the inhibitors was also active against 3C protease from coxsackievirus B3. These inhibitors could be potentially developed into anti-coronaviral and anti-picornaviral agents. |
| doi_str_mv | 10.1016/j.bmc.2010.09.050 |
| format | Article |
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A series of pyrazolone compounds as possible SARS-CoV 3CL protease inhibitors were designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide in which several showed potent inhibition against the 3CL protease. Interestingly, one of the inhibitors was also active against 3C protease from coxsackievirus B3. These inhibitors could be potentially developed into anti-coronaviral and anti-picornaviral agents.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2010.09.050</identifier><identifier>PMID: 20947359</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>3C Viral Proteases ; 3CL protease ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Binding Sites ; Biological and medical sciences ; Catalytic Domain ; Computer modeling ; Computer Simulation ; Coronavirus 3C Proteases ; Coxsackievirus ; Coxsackievirus B3 ; Cysteine Endopeptidases - metabolism ; Enterovirus B, Human - enzymology ; Humans ; Medical sciences ; Pharmacology. Drug treatments ; Protease Inhibitors - chemical synthesis ; Protease Inhibitors - chemistry ; Protease Inhibitors - pharmacology ; Pyrazolone ; Pyrazolones - chemical synthesis ; Pyrazolones - chemistry ; Pyrazolones - pharmacology ; SARS-CoV ; Structure-Activity Relationship ; Viral Proteins - antagonists & inhibitors ; Viral Proteins - metabolism</subject><ispartof>Bioorganic & medicinal chemistry, 2010-11, Vol.18 (22), p.7849-7854</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2010 Elsevier Ltd. All rights reserved.</rights><rights>Copyright © 2010 Elsevier Ltd. All rights reserved. 2010 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c578t-5277a19e2b53071a1627efab227068b9ec29711d8f420a0e40126a3a77a20a093</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2010.09.050$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23420782$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20947359$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ramajayam, R.</creatorcontrib><creatorcontrib>Tan, Kian-Pin</creatorcontrib><creatorcontrib>Liu, Hun-Ge</creatorcontrib><creatorcontrib>Liang, Po-Huang</creatorcontrib><title>Synthesis and evaluation of pyrazolone compounds as SARS-coronavirus 3C-like protease inhibitors</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A series of pyrazolone compounds as possible SARS-CoV 3CL protease inhibitors were designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide in which several showed potent inhibition against the 3CL protease. Interestingly, one of the inhibitors was also active against 3C protease from coxsackievirus B3. These inhibitors could be potentially developed into anti-coronaviral and anti-picornaviral agents.
A series of pyrazolone compounds as possible SARS-CoV 3CL protease inhibitors were designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide in which several showed potent inhibition against the 3CL protease. Interestingly, one of the inhibitors was also active against 3C protease from coxsackievirus B3. These inhibitors could be potentially developed into anti-coronaviral and anti-picornaviral agents.</description><subject>3C Viral Proteases</subject><subject>3CL protease</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>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>Catalytic Domain</subject><subject>Computer modeling</subject><subject>Computer Simulation</subject><subject>Coronavirus 3C Proteases</subject><subject>Coxsackievirus</subject><subject>Coxsackievirus B3</subject><subject>Cysteine Endopeptidases - metabolism</subject><subject>Enterovirus B, Human - enzymology</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Protease Inhibitors - chemical synthesis</subject><subject>Protease Inhibitors - chemistry</subject><subject>Protease Inhibitors - pharmacology</subject><subject>Pyrazolone</subject><subject>Pyrazolones - chemical synthesis</subject><subject>Pyrazolones - chemistry</subject><subject>Pyrazolones - pharmacology</subject><subject>SARS-CoV</subject><subject>Structure-Activity Relationship</subject><subject>Viral Proteins - antagonists & inhibitors</subject><subject>Viral Proteins - metabolism</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUGP0zAQhS0EYrsLP4ALygXtKWXsOHYsJKRVxQLSSkgUzsZxJtQlsYudVCq_HlctC1zgNBrN955m5hHyjMKSAhUvt8t2tEsGuQe1hBoekAXlgpdVpehDsgAlmhIaJS7IZUpbAGBc0cfkgoHisqrVgnxZH_y0weRSYXxX4N4Ms5lc8EXoi90hmh9hCB4LG8ZdmH2XsVSsbz6uSxti8Gbv4pyKalUO7hsWuxgmNAkL5zeudVOI6Ql51Jsh4dNzvSKfb998Wr0r7z68fb-6uSttLZuprJmUhipkbV2BpIYKJrE3LWMSRNMqtExJSrum5wwMIAfKhKlMVh17VV2R1yff3dyO2Fn0UzSD3kU3mnjQwTj998S7jf4a9lpSJjlvssH12SCG7zOmSY8uWRwG4zHMSStKKZdC8P-SUjDW1A2ITNITaWNIKWJ_vw8FfYxQb3WOUB8j1KB0jjBrnv95yL3iV2YZeHEGTLJm6KPx1qXfXJU_JBuWuVcnDvPb9w6jTtaht9i5iHbSXXD_WOMnR2y6CQ</recordid><startdate>20101115</startdate><enddate>20101115</enddate><creator>Ramajayam, R.</creator><creator>Tan, Kian-Pin</creator><creator>Liu, Hun-Ge</creator><creator>Liang, Po-Huang</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><scope>7QO</scope><scope>7U9</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>5PM</scope></search><sort><creationdate>20101115</creationdate><title>Synthesis and evaluation of pyrazolone compounds as SARS-coronavirus 3C-like protease inhibitors</title><author>Ramajayam, R. ; Tan, Kian-Pin ; Liu, Hun-Ge ; Liang, Po-Huang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c578t-5277a19e2b53071a1627efab227068b9ec29711d8f420a0e40126a3a77a20a093</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>3C Viral Proteases</topic><topic>3CL protease</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>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>Catalytic Domain</topic><topic>Computer modeling</topic><topic>Computer Simulation</topic><topic>Coronavirus 3C Proteases</topic><topic>Coxsackievirus</topic><topic>Coxsackievirus B3</topic><topic>Cysteine Endopeptidases - metabolism</topic><topic>Enterovirus B, Human - enzymology</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Protease Inhibitors - chemical synthesis</topic><topic>Protease Inhibitors - chemistry</topic><topic>Protease Inhibitors - pharmacology</topic><topic>Pyrazolone</topic><topic>Pyrazolones - chemical synthesis</topic><topic>Pyrazolones - chemistry</topic><topic>Pyrazolones - pharmacology</topic><topic>SARS-CoV</topic><topic>Structure-Activity Relationship</topic><topic>Viral Proteins - antagonists & inhibitors</topic><topic>Viral Proteins - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ramajayam, R.</creatorcontrib><creatorcontrib>Tan, Kian-Pin</creatorcontrib><creatorcontrib>Liu, Hun-Ge</creatorcontrib><creatorcontrib>Liang, Po-Huang</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><collection>Biotechnology Research Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ramajayam, R.</au><au>Tan, Kian-Pin</au><au>Liu, Hun-Ge</au><au>Liang, Po-Huang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and evaluation of pyrazolone compounds as SARS-coronavirus 3C-like protease inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2010-11-15</date><risdate>2010</risdate><volume>18</volume><issue>22</issue><spage>7849</spage><epage>7854</epage><pages>7849-7854</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A series of pyrazolone compounds as possible SARS-CoV 3CL protease inhibitors were designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide in which several showed potent inhibition against the 3CL protease. Interestingly, one of the inhibitors was also active against 3C protease from coxsackievirus B3. These inhibitors could be potentially developed into anti-coronaviral and anti-picornaviral agents.
A series of pyrazolone compounds as possible SARS-CoV 3CL protease inhibitors were designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide in which several showed potent inhibition against the 3CL protease. Interestingly, one of the inhibitors was also active against 3C protease from coxsackievirus B3. These inhibitors could be potentially developed into anti-coronaviral and anti-picornaviral agents.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20947359</pmid><doi>10.1016/j.bmc.2010.09.050</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | 3C Viral Proteases 3CL protease Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Binding Sites Biological and medical sciences Catalytic Domain Computer modeling Computer Simulation Coronavirus 3C Proteases Coxsackievirus Coxsackievirus B3 Cysteine Endopeptidases - metabolism Enterovirus B, Human - enzymology Humans Medical sciences Pharmacology. Drug treatments Protease Inhibitors - chemical synthesis Protease Inhibitors - chemistry Protease Inhibitors - pharmacology Pyrazolone Pyrazolones - chemical synthesis Pyrazolones - chemistry Pyrazolones - pharmacology SARS-CoV Structure-Activity Relationship Viral Proteins - antagonists & inhibitors Viral Proteins - metabolism |
| title | Synthesis and evaluation of pyrazolone compounds as SARS-coronavirus 3C-like protease inhibitors |
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