Dihydropyrancarboxamides Related to Zanamivir: A New Series of Inhibitors of Influenza Virus Sialidases. 1. Discovery, Synthesis, Biological Activity, and Structure−Activity Relationships of 4-Guanidino- and 4-Amino-4H-pyran-6-carboxamides
4-Amino- and 4-guanidino-4H-pyran-6-carboxamides 4 and 5 related to zanamivir (GG167) are a new class of inhibitors of influenza virus sialidases. Structure−activity studies reveal that, in general, secondary amides are weak inhibitors of both influenza A and B viral sialidases. However, tertiary am...
Gespeichert in:
| Veröffentlicht in: | Journal of medicinal chemistry 1998-03, Vol.41 (6), p.787-797 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 797 |
|---|---|
| container_issue | 6 |
| container_start_page | 787 |
| container_title | Journal of medicinal chemistry |
| container_volume | 41 |
| creator | Smith, Paul W Sollis, Steven L Howes, Peter D Cherry, Peter C Starkey, Ian D Cobley, Kevin N Weston, Helen Scicinski, Jan Merritt, Andrew Whittington, Andrew Wyatt, Paul Taylor, Neil Green, Darren Bethell, Richard Madar, Safia Fenton, Robert J Morley, Peter J Pateman, Tony Beresford, Alan |
| description | 4-Amino- and 4-guanidino-4H-pyran-6-carboxamides 4 and 5 related to zanamivir (GG167) are a new class of inhibitors of influenza virus sialidases. Structure−activity studies reveal that, in general, secondary amides are weak inhibitors of both influenza A and B viral sialidases. However, tertiary amides, which contain one or more small alkyl groups, show much greater inhibitory activity, particularly against the influenza A virus enzyme. The sialidase inhibitory activities of these compounds correlate well with their in vitro antiviral efficacy, and several of the most potent analogues displayed useful antiviral activity in vivo when evaluated in a mouse model of influenza A virus infection. Carboxamides which were highly active sialidase inhibitors in vitro also showed good antiviral activity in the mouse efficacy model of influenza A infection when administered intranasally but displayed modest activity when delivered by the intraperitoneal route. |
| doi_str_mv | 10.1021/jm970374b |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_79762189</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>17445616</sourcerecordid><originalsourceid>FETCH-LOGICAL-a427t-d7ecb1b0c8d47435ce95ea1611a83824207403a17e97b165e5ad4db6fb8dc91f3</originalsourceid><addsrcrecordid>eNqFks9u1DAQxiMEKtvCgQdA8gE41YvtOHbCbWnLtqKCqikgcbGc2GG9JPZiO6XLiSNcecQ-Aw9A9g8rbpys8ffzjL-ZSZJHGI0xIvj5vCs4Sjmt7iQjnBEEaY7o3WSEECGQMJLeT_ZDmCOEUkzSvWSvyAjLsmyU_D42s6XybrH00tbSV-5GdkbpAC51K6NWIDrwUdrh8tr4F7fff4IJeKO_glJ7M1CuAWd2ZioTnd9GTdtr-02C98b3AZRGtkbJoMMY4DE4NqF219ovD0G5tHGmgwmH4KVxrftkatmCSR2HSnHQpVWgjL6vY-_17Y9ff5XNz4yzYWYW65oUTntpjTLWwfUzCifdKqCncG0MMvivtwfJvUa2QT_cngfJu1cnV0en8Pzt9Oxocg4lJTxCxXVd4QrVuaKcplmti0xLzDCWeZoTShCnKJWY64JXmGU6k4qqijVVruoCN-lB8myTd-Hdl16HKLrBvm5babXrg-AFZwTnxX9BzCnNGGYD-HgL9lWnlVh400m_FNt5DvqTrS7D0M1mNVQTdhghCLFilQZuMBOivtnJ0n8WjKc8E1cXpSgRmV68vizFh4F_uuFlHcTc9d4ObRMYidX2id32pX8ADRnO5g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>17445616</pqid></control><display><type>article</type><title>Dihydropyrancarboxamides Related to Zanamivir: A New Series of Inhibitors of Influenza Virus Sialidases. 1. Discovery, Synthesis, Biological Activity, and Structure−Activity Relationships of 4-Guanidino- and 4-Amino-4H-pyran-6-carboxamides</title><source>ACS Publications</source><source>MEDLINE</source><creator>Smith, Paul W ; Sollis, Steven L ; Howes, Peter D ; Cherry, Peter C ; Starkey, Ian D ; Cobley, Kevin N ; Weston, Helen ; Scicinski, Jan ; Merritt, Andrew ; Whittington, Andrew ; Wyatt, Paul ; Taylor, Neil ; Green, Darren ; Bethell, Richard ; Madar, Safia ; Fenton, Robert J ; Morley, Peter J ; Pateman, Tony ; Beresford, Alan</creator><creatorcontrib>Smith, Paul W ; Sollis, Steven L ; Howes, Peter D ; Cherry, Peter C ; Starkey, Ian D ; Cobley, Kevin N ; Weston, Helen ; Scicinski, Jan ; Merritt, Andrew ; Whittington, Andrew ; Wyatt, Paul ; Taylor, Neil ; Green, Darren ; Bethell, Richard ; Madar, Safia ; Fenton, Robert J ; Morley, Peter J ; Pateman, Tony ; Beresford, Alan</creatorcontrib><description>4-Amino- and 4-guanidino-4H-pyran-6-carboxamides 4 and 5 related to zanamivir (GG167) are a new class of inhibitors of influenza virus sialidases. Structure−activity studies reveal that, in general, secondary amides are weak inhibitors of both influenza A and B viral sialidases. However, tertiary amides, which contain one or more small alkyl groups, show much greater inhibitory activity, particularly against the influenza A virus enzyme. The sialidase inhibitory activities of these compounds correlate well with their in vitro antiviral efficacy, and several of the most potent analogues displayed useful antiviral activity in vivo when evaluated in a mouse model of influenza A virus infection. Carboxamides which were highly active sialidase inhibitors in vitro also showed good antiviral activity in the mouse efficacy model of influenza A infection when administered intranasally but displayed modest activity when delivered by the intraperitoneal route.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm970374b</identifier><identifier>PMID: 9526555</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>4-amino-4H-pyran-6-carboxamide ; 4-guanidino-4H-pyran-6-carboxamide ; Administration, Intranasal ; Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacokinetics ; Antiviral Agents - pharmacology ; Biological and medical sciences ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacokinetics ; Enzyme Inhibitors - pharmacology ; Guanidines - chemical synthesis ; Guanidines - chemistry ; Guanidines - pharmacokinetics ; Guanidines - pharmacology ; Influenza A virus ; Influenza A virus - drug effects ; Influenza A virus - enzymology ; Influenza B virus - drug effects ; Influenza B virus - enzymology ; Injections, Intraperitoneal ; Medical sciences ; Mice ; Neuraminidase - antagonists & inhibitors ; Orthomyxoviridae Infections - drug therapy ; Orthomyxoviridae Infections - enzymology ; Pharmacology. Drug treatments ; Pyrans - chemical synthesis ; Pyrans - chemistry ; Pyrans - pharmacokinetics ; Pyrans - pharmacology ; Sialic Acids - chemistry ; Sialic Acids - pharmacokinetics ; Sialic Acids - pharmacology ; Structure-Activity Relationship ; Zanamivir</subject><ispartof>Journal of medicinal chemistry, 1998-03, Vol.41 (6), p.787-797</ispartof><rights>Copyright © 1998 American Chemical Society</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm970374b$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm970374b$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2200696$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9526555$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Smith, Paul W</creatorcontrib><creatorcontrib>Sollis, Steven L</creatorcontrib><creatorcontrib>Howes, Peter D</creatorcontrib><creatorcontrib>Cherry, Peter C</creatorcontrib><creatorcontrib>Starkey, Ian D</creatorcontrib><creatorcontrib>Cobley, Kevin N</creatorcontrib><creatorcontrib>Weston, Helen</creatorcontrib><creatorcontrib>Scicinski, Jan</creatorcontrib><creatorcontrib>Merritt, Andrew</creatorcontrib><creatorcontrib>Whittington, Andrew</creatorcontrib><creatorcontrib>Wyatt, Paul</creatorcontrib><creatorcontrib>Taylor, Neil</creatorcontrib><creatorcontrib>Green, Darren</creatorcontrib><creatorcontrib>Bethell, Richard</creatorcontrib><creatorcontrib>Madar, Safia</creatorcontrib><creatorcontrib>Fenton, Robert J</creatorcontrib><creatorcontrib>Morley, Peter J</creatorcontrib><creatorcontrib>Pateman, Tony</creatorcontrib><creatorcontrib>Beresford, Alan</creatorcontrib><title>Dihydropyrancarboxamides Related to Zanamivir: A New Series of Inhibitors of Influenza Virus Sialidases. 1. Discovery, Synthesis, Biological Activity, and Structure−Activity Relationships of 4-Guanidino- and 4-Amino-4H-pyran-6-carboxamides</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>4-Amino- and 4-guanidino-4H-pyran-6-carboxamides 4 and 5 related to zanamivir (GG167) are a new class of inhibitors of influenza virus sialidases. Structure−activity studies reveal that, in general, secondary amides are weak inhibitors of both influenza A and B viral sialidases. However, tertiary amides, which contain one or more small alkyl groups, show much greater inhibitory activity, particularly against the influenza A virus enzyme. The sialidase inhibitory activities of these compounds correlate well with their in vitro antiviral efficacy, and several of the most potent analogues displayed useful antiviral activity in vivo when evaluated in a mouse model of influenza A virus infection. Carboxamides which were highly active sialidase inhibitors in vitro also showed good antiviral activity in the mouse efficacy model of influenza A infection when administered intranasally but displayed modest activity when delivered by the intraperitoneal route.</description><subject>4-amino-4H-pyran-6-carboxamide</subject><subject>4-guanidino-4H-pyran-6-carboxamide</subject><subject>Administration, Intranasal</subject><subject>Animals</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 - pharmacokinetics</subject><subject>Antiviral Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacokinetics</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Guanidines - chemical synthesis</subject><subject>Guanidines - chemistry</subject><subject>Guanidines - pharmacokinetics</subject><subject>Guanidines - pharmacology</subject><subject>Influenza A virus</subject><subject>Influenza A virus - drug effects</subject><subject>Influenza A virus - enzymology</subject><subject>Influenza B virus - drug effects</subject><subject>Influenza B virus - enzymology</subject><subject>Injections, Intraperitoneal</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Neuraminidase - antagonists & inhibitors</subject><subject>Orthomyxoviridae Infections - drug therapy</subject><subject>Orthomyxoviridae Infections - enzymology</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrans - chemical synthesis</subject><subject>Pyrans - chemistry</subject><subject>Pyrans - pharmacokinetics</subject><subject>Pyrans - pharmacology</subject><subject>Sialic Acids - chemistry</subject><subject>Sialic Acids - pharmacokinetics</subject><subject>Sialic Acids - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Zanamivir</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFks9u1DAQxiMEKtvCgQdA8gE41YvtOHbCbWnLtqKCqikgcbGc2GG9JPZiO6XLiSNcecQ-Aw9A9g8rbpys8ffzjL-ZSZJHGI0xIvj5vCs4Sjmt7iQjnBEEaY7o3WSEECGQMJLeT_ZDmCOEUkzSvWSvyAjLsmyU_D42s6XybrH00tbSV-5GdkbpAC51K6NWIDrwUdrh8tr4F7fff4IJeKO_glJ7M1CuAWd2ZioTnd9GTdtr-02C98b3AZRGtkbJoMMY4DE4NqF219ovD0G5tHGmgwmH4KVxrftkatmCSR2HSnHQpVWgjL6vY-_17Y9ff5XNz4yzYWYW65oUTntpjTLWwfUzCifdKqCncG0MMvivtwfJvUa2QT_cngfJu1cnV0en8Pzt9Oxocg4lJTxCxXVd4QrVuaKcplmti0xLzDCWeZoTShCnKJWY64JXmGU6k4qqijVVruoCN-lB8myTd-Hdl16HKLrBvm5babXrg-AFZwTnxX9BzCnNGGYD-HgL9lWnlVh400m_FNt5DvqTrS7D0M1mNVQTdhghCLFilQZuMBOivtnJ0n8WjKc8E1cXpSgRmV68vizFh4F_uuFlHcTc9d4ObRMYidX2id32pX8ADRnO5g</recordid><startdate>19980312</startdate><enddate>19980312</enddate><creator>Smith, Paul W</creator><creator>Sollis, Steven L</creator><creator>Howes, Peter D</creator><creator>Cherry, Peter C</creator><creator>Starkey, Ian D</creator><creator>Cobley, Kevin N</creator><creator>Weston, Helen</creator><creator>Scicinski, Jan</creator><creator>Merritt, Andrew</creator><creator>Whittington, Andrew</creator><creator>Wyatt, Paul</creator><creator>Taylor, Neil</creator><creator>Green, Darren</creator><creator>Bethell, Richard</creator><creator>Madar, Safia</creator><creator>Fenton, Robert J</creator><creator>Morley, Peter J</creator><creator>Pateman, Tony</creator><creator>Beresford, Alan</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7T7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>19980312</creationdate><title>Dihydropyrancarboxamides Related to Zanamivir: A New Series of Inhibitors of Influenza Virus Sialidases. 1. Discovery, Synthesis, Biological Activity, and Structure−Activity Relationships of 4-Guanidino- and 4-Amino-4H-pyran-6-carboxamides</title><author>Smith, Paul W ; Sollis, Steven L ; Howes, Peter D ; Cherry, Peter C ; Starkey, Ian D ; Cobley, Kevin N ; Weston, Helen ; Scicinski, Jan ; Merritt, Andrew ; Whittington, Andrew ; Wyatt, Paul ; Taylor, Neil ; Green, Darren ; Bethell, Richard ; Madar, Safia ; Fenton, Robert J ; Morley, Peter J ; Pateman, Tony ; Beresford, Alan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a427t-d7ecb1b0c8d47435ce95ea1611a83824207403a17e97b165e5ad4db6fb8dc91f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>4-amino-4H-pyran-6-carboxamide</topic><topic>4-guanidino-4H-pyran-6-carboxamide</topic><topic>Administration, Intranasal</topic><topic>Animals</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 - pharmacokinetics</topic><topic>Antiviral Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacokinetics</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Guanidines - chemical synthesis</topic><topic>Guanidines - chemistry</topic><topic>Guanidines - pharmacokinetics</topic><topic>Guanidines - pharmacology</topic><topic>Influenza A virus</topic><topic>Influenza A virus - drug effects</topic><topic>Influenza A virus - enzymology</topic><topic>Influenza B virus - drug effects</topic><topic>Influenza B virus - enzymology</topic><topic>Injections, Intraperitoneal</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Neuraminidase - antagonists & inhibitors</topic><topic>Orthomyxoviridae Infections - drug therapy</topic><topic>Orthomyxoviridae Infections - enzymology</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrans - chemical synthesis</topic><topic>Pyrans - chemistry</topic><topic>Pyrans - pharmacokinetics</topic><topic>Pyrans - pharmacology</topic><topic>Sialic Acids - chemistry</topic><topic>Sialic Acids - pharmacokinetics</topic><topic>Sialic Acids - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Zanamivir</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Smith, Paul W</creatorcontrib><creatorcontrib>Sollis, Steven L</creatorcontrib><creatorcontrib>Howes, Peter D</creatorcontrib><creatorcontrib>Cherry, Peter C</creatorcontrib><creatorcontrib>Starkey, Ian D</creatorcontrib><creatorcontrib>Cobley, Kevin N</creatorcontrib><creatorcontrib>Weston, Helen</creatorcontrib><creatorcontrib>Scicinski, Jan</creatorcontrib><creatorcontrib>Merritt, Andrew</creatorcontrib><creatorcontrib>Whittington, Andrew</creatorcontrib><creatorcontrib>Wyatt, Paul</creatorcontrib><creatorcontrib>Taylor, Neil</creatorcontrib><creatorcontrib>Green, Darren</creatorcontrib><creatorcontrib>Bethell, Richard</creatorcontrib><creatorcontrib>Madar, Safia</creatorcontrib><creatorcontrib>Fenton, Robert J</creatorcontrib><creatorcontrib>Morley, Peter J</creatorcontrib><creatorcontrib>Pateman, Tony</creatorcontrib><creatorcontrib>Beresford, Alan</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Smith, Paul W</au><au>Sollis, Steven L</au><au>Howes, Peter D</au><au>Cherry, Peter C</au><au>Starkey, Ian D</au><au>Cobley, Kevin N</au><au>Weston, Helen</au><au>Scicinski, Jan</au><au>Merritt, Andrew</au><au>Whittington, Andrew</au><au>Wyatt, Paul</au><au>Taylor, Neil</au><au>Green, Darren</au><au>Bethell, Richard</au><au>Madar, Safia</au><au>Fenton, Robert J</au><au>Morley, Peter J</au><au>Pateman, Tony</au><au>Beresford, Alan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dihydropyrancarboxamides Related to Zanamivir: A New Series of Inhibitors of Influenza Virus Sialidases. 1. Discovery, Synthesis, Biological Activity, and Structure−Activity Relationships of 4-Guanidino- and 4-Amino-4H-pyran-6-carboxamides</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1998-03-12</date><risdate>1998</risdate><volume>41</volume><issue>6</issue><spage>787</spage><epage>797</epage><pages>787-797</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>4-Amino- and 4-guanidino-4H-pyran-6-carboxamides 4 and 5 related to zanamivir (GG167) are a new class of inhibitors of influenza virus sialidases. Structure−activity studies reveal that, in general, secondary amides are weak inhibitors of both influenza A and B viral sialidases. However, tertiary amides, which contain one or more small alkyl groups, show much greater inhibitory activity, particularly against the influenza A virus enzyme. The sialidase inhibitory activities of these compounds correlate well with their in vitro antiviral efficacy, and several of the most potent analogues displayed useful antiviral activity in vivo when evaluated in a mouse model of influenza A virus infection. Carboxamides which were highly active sialidase inhibitors in vitro also showed good antiviral activity in the mouse efficacy model of influenza A infection when administered intranasally but displayed modest activity when delivered by the intraperitoneal route.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>9526555</pmid><doi>10.1021/jm970374b</doi><tpages>11</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1998-03, Vol.41 (6), p.787-797 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_79762189 |
| source | ACS Publications; MEDLINE |
| subjects | 4-amino-4H-pyran-6-carboxamide 4-guanidino-4H-pyran-6-carboxamide Administration, Intranasal Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacokinetics Antiviral Agents - pharmacology Biological and medical sciences Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacokinetics Enzyme Inhibitors - pharmacology Guanidines - chemical synthesis Guanidines - chemistry Guanidines - pharmacokinetics Guanidines - pharmacology Influenza A virus Influenza A virus - drug effects Influenza A virus - enzymology Influenza B virus - drug effects Influenza B virus - enzymology Injections, Intraperitoneal Medical sciences Mice Neuraminidase - antagonists & inhibitors Orthomyxoviridae Infections - drug therapy Orthomyxoviridae Infections - enzymology Pharmacology. Drug treatments Pyrans - chemical synthesis Pyrans - chemistry Pyrans - pharmacokinetics Pyrans - pharmacology Sialic Acids - chemistry Sialic Acids - pharmacokinetics Sialic Acids - pharmacology Structure-Activity Relationship Zanamivir |
| title | Dihydropyrancarboxamides Related to Zanamivir: A New Series of Inhibitors of Influenza Virus Sialidases. 1. Discovery, Synthesis, Biological Activity, and Structure−Activity Relationships of 4-Guanidino- and 4-Amino-4H-pyran-6-carboxamides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-09T11%3A21%3A37IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Dihydropyrancarboxamides%20Related%20to%20Zanamivir:%E2%80%89%20A%20New%20Series%20of%20Inhibitors%20of%20Influenza%20Virus%20Sialidases.%201.%20Discovery,%20Synthesis,%20Biological%20Activity,%20and%20Structure%E2%88%92Activity%20Relationships%20of%204-Guanidino-%20and%204-Amino-4H-pyran-6-carboxamides&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=Smith,%20Paul%20W&rft.date=1998-03-12&rft.volume=41&rft.issue=6&rft.spage=787&rft.epage=797&rft.pages=787-797&rft.issn=0022-2623&rft.eissn=1520-4804&rft.coden=JMCMAR&rft_id=info:doi/10.1021/jm970374b&rft_dat=%3Cproquest_pubme%3E17445616%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=17445616&rft_id=info:pmid/9526555&rfr_iscdi=true |