N-Long-chain Monoacylated Derivatives of 2,6-Diaminopyridine with Antiviral Activity
N-Monoacyl-2,6-diaminopyridines (2a—c) and N,N′-diacyl-2,6-diaminopyridines (3a—c) were synthesized from 2,6-diaminopyridine by acylation with the corresponding acyl halide or by dehydration with the corresponding carboxylic acid using 1,3-dicyclohexylcarbodiimide (DCC). The antiviral activities of...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2007, Vol.55(1), pp.111-114 |
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| creator | Mibu, Nobuko Yokomizo, Kazumi Kashige, Nobuhiro Miake, Fumio Miyata, Takeshi Uyeda, Masaru Sumoto, Kunihiro |
| description | N-Monoacyl-2,6-diaminopyridines (2a—c) and N,N′-diacyl-2,6-diaminopyridines (3a—c) were synthesized from 2,6-diaminopyridine by acylation with the corresponding acyl halide or by dehydration with the corresponding carboxylic acid using 1,3-dicyclohexylcarbodiimide (DCC). The antiviral activities of N-monoacyl- and N,N′-diacyl-2,6-diaminopyridines (2a—c and 3a—c) were estimated using plaque reduction assay with HSV-1. All N-monoacyl derivatives (2a—c) showed significant anti-herpes simplex virus (HSV)-1 activity (EC50=15.3—18.5 μg/ml). The CC50 values of 2a—c measured using Vero cells ranged at 37.5—50.0 μg/ml. These compounds showed no significant antibacterial activities with Escherichia coli or Staphylococcus aureus even at a concentration of 1 mg/ml. The N,N′-diacyl derivatives (3a—c) showed no significant anti-HSV-1 activity. |
| doi_str_mv | 10.1248/cpb.55.111 |
| format | Article |
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The antiviral activities of N-monoacyl- and N,N′-diacyl-2,6-diaminopyridines (2a—c and 3a—c) were estimated using plaque reduction assay with HSV-1. All N-monoacyl derivatives (2a—c) showed significant anti-herpes simplex virus (HSV)-1 activity (EC50=15.3—18.5 μg/ml). The CC50 values of 2a—c measured using Vero cells ranged at 37.5—50.0 μg/ml. These compounds showed no significant antibacterial activities with Escherichia coli or Staphylococcus aureus even at a concentration of 1 mg/ml. The N,N′-diacyl derivatives (3a—c) showed no significant anti-HSV-1 activity.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.55.111</identifier><identifier>PMID: 17202712</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>2,6-diaminopyridine ; Acylation ; Animals ; anti-herpes simplex virus (HSV)-1 ; antibacterial activity ; antiviral activity ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Cell Line ; Cercopithecus aethiops ; Escherichia coli ; Herpes simplex virus 1 ; Microbial Sensitivity Tests ; plaque reduction assay ; Pyridines - chemistry ; Pyridines - pharmacology ; Staphylococcus aureus ; Vero Cells</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2007, Vol.55(1), pp.111-114</ispartof><rights>2007 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2007</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c526t-508321dff21a8628580d8475bcc477d115e6ba087356db1fcde9363d1dd4b8a23</citedby><cites>FETCH-LOGICAL-c526t-508321dff21a8628580d8475bcc477d115e6ba087356db1fcde9363d1dd4b8a23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,1884,4025,27928,27929,27930</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17202712$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mibu, Nobuko</creatorcontrib><creatorcontrib>Yokomizo, Kazumi</creatorcontrib><creatorcontrib>Kashige, Nobuhiro</creatorcontrib><creatorcontrib>Miake, Fumio</creatorcontrib><creatorcontrib>Miyata, Takeshi</creatorcontrib><creatorcontrib>Uyeda, Masaru</creatorcontrib><creatorcontrib>Sumoto, Kunihiro</creatorcontrib><title>N-Long-chain Monoacylated Derivatives of 2,6-Diaminopyridine with Antiviral Activity</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>N-Monoacyl-2,6-diaminopyridines (2a—c) and N,N′-diacyl-2,6-diaminopyridines (3a—c) were synthesized from 2,6-diaminopyridine by acylation with the corresponding acyl halide or by dehydration with the corresponding carboxylic acid using 1,3-dicyclohexylcarbodiimide (DCC). The antiviral activities of N-monoacyl- and N,N′-diacyl-2,6-diaminopyridines (2a—c and 3a—c) were estimated using plaque reduction assay with HSV-1. All N-monoacyl derivatives (2a—c) showed significant anti-herpes simplex virus (HSV)-1 activity (EC50=15.3—18.5 μg/ml). The CC50 values of 2a—c measured using Vero cells ranged at 37.5—50.0 μg/ml. These compounds showed no significant antibacterial activities with Escherichia coli or Staphylococcus aureus even at a concentration of 1 mg/ml. The N,N′-diacyl derivatives (3a—c) showed no significant anti-HSV-1 activity.</description><subject>2,6-diaminopyridine</subject><subject>Acylation</subject><subject>Animals</subject><subject>anti-herpes simplex virus (HSV)-1</subject><subject>antibacterial activity</subject><subject>antiviral activity</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Cell Line</subject><subject>Cercopithecus aethiops</subject><subject>Escherichia coli</subject><subject>Herpes simplex virus 1</subject><subject>Microbial Sensitivity Tests</subject><subject>plaque reduction assay</subject><subject>Pyridines - chemistry</subject><subject>Pyridines - pharmacology</subject><subject>Staphylococcus aureus</subject><subject>Vero Cells</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0c1qGzEUBWBREhI3zaYPEAYCXZSOqyuNfmYVTNKmASfdpGuhkTSxzFhypHGK374yNglk040kuJ8OXA5CnwFPgTTyu1l3U8amAPABTYA2omaE0CM0wRi3NaGcnqKPOS8xJgwLeoJOQRBMBJAJenyo5zE81WahfajuY4jabAc9OlvduORf9OhfXK5iX5FvvL7xeuVDXG-Ttz646q8fF9UsFOOTHqqZ2b3G7Sd03Oshu_PDfYb-_PzxeP2rnv--vbuezWvDCB9rhiUlYPuegJacSCaxlY1gnTGNEBaAOd5pLAVl3HbQG-vasowFa5tOakLP0Jd97jrF543Lo1r5bNww6ODiJisuaVt-i_9CaCVrG4oLvHwHl3GTQllCQcNxgznDO_V1r0yKOSfXq3XyK522CrDaVaJKJYoxVSop-OIQuelWzr7RQwcFXO3BMo_6yb0CnUZvBveatT9K5NtkoZNygf4D7EqcEQ</recordid><startdate>2007</startdate><enddate>2007</enddate><creator>Mibu, Nobuko</creator><creator>Yokomizo, Kazumi</creator><creator>Kashige, Nobuhiro</creator><creator>Miake, Fumio</creator><creator>Miyata, Takeshi</creator><creator>Uyeda, Masaru</creator><creator>Sumoto, Kunihiro</creator><general>The Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7QL</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>2007</creationdate><title>N-Long-chain Monoacylated Derivatives of 2,6-Diaminopyridine with Antiviral Activity</title><author>Mibu, Nobuko ; Yokomizo, Kazumi ; Kashige, Nobuhiro ; Miake, Fumio ; Miyata, Takeshi ; Uyeda, Masaru ; Sumoto, Kunihiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c526t-508321dff21a8628580d8475bcc477d115e6ba087356db1fcde9363d1dd4b8a23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>2,6-diaminopyridine</topic><topic>Acylation</topic><topic>Animals</topic><topic>anti-herpes simplex virus (HSV)-1</topic><topic>antibacterial activity</topic><topic>antiviral activity</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Cell Line</topic><topic>Cercopithecus aethiops</topic><topic>Escherichia coli</topic><topic>Herpes simplex virus 1</topic><topic>Microbial Sensitivity Tests</topic><topic>plaque reduction assay</topic><topic>Pyridines - chemistry</topic><topic>Pyridines - pharmacology</topic><topic>Staphylococcus aureus</topic><topic>Vero Cells</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mibu, Nobuko</creatorcontrib><creatorcontrib>Yokomizo, Kazumi</creatorcontrib><creatorcontrib>Kashige, Nobuhiro</creatorcontrib><creatorcontrib>Miake, Fumio</creatorcontrib><creatorcontrib>Miyata, Takeshi</creatorcontrib><creatorcontrib>Uyeda, Masaru</creatorcontrib><creatorcontrib>Sumoto, Kunihiro</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mibu, Nobuko</au><au>Yokomizo, Kazumi</au><au>Kashige, Nobuhiro</au><au>Miake, Fumio</au><au>Miyata, Takeshi</au><au>Uyeda, Masaru</au><au>Sumoto, Kunihiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N-Long-chain Monoacylated Derivatives of 2,6-Diaminopyridine with Antiviral Activity</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2007</date><risdate>2007</risdate><volume>55</volume><issue>1</issue><spage>111</spage><epage>114</epage><pages>111-114</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>N-Monoacyl-2,6-diaminopyridines (2a—c) and N,N′-diacyl-2,6-diaminopyridines (3a—c) were synthesized from 2,6-diaminopyridine by acylation with the corresponding acyl halide or by dehydration with the corresponding carboxylic acid using 1,3-dicyclohexylcarbodiimide (DCC). The antiviral activities of N-monoacyl- and N,N′-diacyl-2,6-diaminopyridines (2a—c and 3a—c) were estimated using plaque reduction assay with HSV-1. All N-monoacyl derivatives (2a—c) showed significant anti-herpes simplex virus (HSV)-1 activity (EC50=15.3—18.5 μg/ml). The CC50 values of 2a—c measured using Vero cells ranged at 37.5—50.0 μg/ml. These compounds showed no significant antibacterial activities with Escherichia coli or Staphylococcus aureus even at a concentration of 1 mg/ml. 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| subjects | 2,6-diaminopyridine Acylation Animals anti-herpes simplex virus (HSV)-1 antibacterial activity antiviral activity Antiviral Agents - chemistry Antiviral Agents - pharmacology Cell Line Cercopithecus aethiops Escherichia coli Herpes simplex virus 1 Microbial Sensitivity Tests plaque reduction assay Pyridines - chemistry Pyridines - pharmacology Staphylococcus aureus Vero Cells |
| title | N-Long-chain Monoacylated Derivatives of 2,6-Diaminopyridine with Antiviral Activity |
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