Respiratory syncytial virus fusion inhibitors. Part 3: Water-soluble benzimidazol-2-one derivatives with antiviral activity in vivo
The introduction of acidic and basic functionality into the side chains R and R′ of respiratory syncytial virus (RSV) fusion inhibitors 2 was examined in an effort to identify compounds suitable for evaluation in vivo in the cotton rat model of RSV infection following administration as a small parti...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2006-03, Vol.16 (5), p.1115-1122 |
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| creator | Yu, Kuo-Long Wang, Xiangdong Alan Civiello, Rita L. Trehan, Ashok K. Pearce, Bradley C. Yin, Zhiwei Combrink, Keith D. Gulgeze, H. Belgin Zhang, Yi Kadow, Kathleen F. Cianci, Christopher W. Clarke, Junius Genovesi, Eugene V. Medina, Ivette Lamb, Lucinda Wyde, Philip R. Krystal, Mark Meanwell, Nicholas A. |
| description | The introduction of acidic and basic functionality into the side chains R and R′ of respiratory syncytial virus (RSV) fusion inhibitors
2 was examined in an effort to identify compounds suitable for evaluation in vivo in the cotton rat model of RSV infection following administration as a small particle aerosol. Several acid-containing compounds demonstrated potent antiviral activity in cell culture and exhibited efficacy in the cotton rat comparable to ribavirin. In a BALB/c mouse model, the amide
2aab reduced virus titers following oral dosing, establishing the potential of this class of RSV fusion inhibitors to interfere with infection in vivo following topical or systemic administration.
The introduction of acidic and basic functionality into the side chains of respiratory syncytial virus (RSV) fusion inhibitors was examined in an effort to identify compounds suitable for evaluation in vivo in the cotton rat model of RSV infection following administration as a small particle aerosol. The acidic compounds
2r,
2u,
2v,
2w,
2z, and
2aj demonstrated potent antiviral activity in cell culture and exhibited efficacy in the cotton rat comparable to ribavirin. In a BALB/c mouse model, the oxadiazolone
2aj reduced virus titers following subcutaneous dosing, whilst the ester
2az and amide
2aab exhibited efficacy following oral administration. These results established the potential of this class of RSV fusion inhibitors to interfere with infection in vivo following topical or systemic administration. |
| doi_str_mv | 10.1016/j.bmcl.2005.11.109 |
| format | Article |
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2 was examined in an effort to identify compounds suitable for evaluation in vivo in the cotton rat model of RSV infection following administration as a small particle aerosol. Several acid-containing compounds demonstrated potent antiviral activity in cell culture and exhibited efficacy in the cotton rat comparable to ribavirin. In a BALB/c mouse model, the amide
2aab reduced virus titers following oral dosing, establishing the potential of this class of RSV fusion inhibitors to interfere with infection in vivo following topical or systemic administration.
The introduction of acidic and basic functionality into the side chains of respiratory syncytial virus (RSV) fusion inhibitors was examined in an effort to identify compounds suitable for evaluation in vivo in the cotton rat model of RSV infection following administration as a small particle aerosol. The acidic compounds
2r,
2u,
2v,
2w,
2z, and
2aj demonstrated potent antiviral activity in cell culture and exhibited efficacy in the cotton rat comparable to ribavirin. In a BALB/c mouse model, the oxadiazolone
2aj reduced virus titers following subcutaneous dosing, whilst the ester
2az and amide
2aab exhibited efficacy following oral administration. These results established the potential of this class of RSV fusion inhibitors to interfere with infection in vivo following topical or systemic administration.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2005.11.109</identifier><identifier>PMID: 16368233</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Amines - chemistry ; Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral ; Antiviral agents ; Antiviral Agents - adverse effects ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Benzimidazol-2-one derivatives ; Benzimidazoles - adverse effects ; Benzimidazoles - chemical synthesis ; Benzimidazoles - chemistry ; Benzimidazoles - pharmacology ; Biological and medical sciences ; Medical sciences ; Membrane Fusion - drug effects ; Mice ; Molecular Structure ; Pharmacology. Drug treatments ; Rats ; Respiratory syncytial virus ; Respiratory Syncytial Viruses - drug effects ; Respiratory Syncytial Viruses - physiology ; Sigmodontinae ; Solubility ; Structure-Activity Relationship ; Water - chemistry ; Water-soluble respiratory syncytial virus inhibitors</subject><ispartof>Bioorganic & medicinal chemistry letters, 2006-03, Vol.16 (5), p.1115-1122</ispartof><rights>2005 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-f0b4d608d17380c6f6b11dfee741018489baae6b503eacd6cac51f4737fc6f663</citedby><cites>FETCH-LOGICAL-c415t-f0b4d608d17380c6f6b11dfee741018489baae6b503eacd6cac51f4737fc6f663</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X05015258$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17557238$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16368233$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yu, Kuo-Long</creatorcontrib><creatorcontrib>Wang, Xiangdong Alan</creatorcontrib><creatorcontrib>Civiello, Rita L.</creatorcontrib><creatorcontrib>Trehan, Ashok K.</creatorcontrib><creatorcontrib>Pearce, Bradley C.</creatorcontrib><creatorcontrib>Yin, Zhiwei</creatorcontrib><creatorcontrib>Combrink, Keith D.</creatorcontrib><creatorcontrib>Gulgeze, H. Belgin</creatorcontrib><creatorcontrib>Zhang, Yi</creatorcontrib><creatorcontrib>Kadow, Kathleen F.</creatorcontrib><creatorcontrib>Cianci, Christopher W.</creatorcontrib><creatorcontrib>Clarke, Junius</creatorcontrib><creatorcontrib>Genovesi, Eugene V.</creatorcontrib><creatorcontrib>Medina, Ivette</creatorcontrib><creatorcontrib>Lamb, Lucinda</creatorcontrib><creatorcontrib>Wyde, Philip R.</creatorcontrib><creatorcontrib>Krystal, Mark</creatorcontrib><creatorcontrib>Meanwell, Nicholas A.</creatorcontrib><title>Respiratory syncytial virus fusion inhibitors. Part 3: Water-soluble benzimidazol-2-one derivatives with antiviral activity in vivo</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The introduction of acidic and basic functionality into the side chains R and R′ of respiratory syncytial virus (RSV) fusion inhibitors
2 was examined in an effort to identify compounds suitable for evaluation in vivo in the cotton rat model of RSV infection following administration as a small particle aerosol. Several acid-containing compounds demonstrated potent antiviral activity in cell culture and exhibited efficacy in the cotton rat comparable to ribavirin. In a BALB/c mouse model, the amide
2aab reduced virus titers following oral dosing, establishing the potential of this class of RSV fusion inhibitors to interfere with infection in vivo following topical or systemic administration.
The introduction of acidic and basic functionality into the side chains of respiratory syncytial virus (RSV) fusion inhibitors was examined in an effort to identify compounds suitable for evaluation in vivo in the cotton rat model of RSV infection following administration as a small particle aerosol. The acidic compounds
2r,
2u,
2v,
2w,
2z, and
2aj demonstrated potent antiviral activity in cell culture and exhibited efficacy in the cotton rat comparable to ribavirin. In a BALB/c mouse model, the oxadiazolone
2aj reduced virus titers following subcutaneous dosing, whilst the ester
2az and amide
2aab exhibited efficacy following oral administration. These results established the potential of this class of RSV fusion inhibitors to interfere with infection in vivo following topical or systemic administration.</description><subject>Amines - chemistry</subject><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral</subject><subject>Antiviral agents</subject><subject>Antiviral Agents - adverse effects</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Benzimidazol-2-one derivatives</subject><subject>Benzimidazoles - adverse effects</subject><subject>Benzimidazoles - chemical synthesis</subject><subject>Benzimidazoles - chemistry</subject><subject>Benzimidazoles - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Medical sciences</subject><subject>Membrane Fusion - drug effects</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Respiratory syncytial virus</subject><subject>Respiratory Syncytial Viruses - drug effects</subject><subject>Respiratory Syncytial Viruses - physiology</subject><subject>Sigmodontinae</subject><subject>Solubility</subject><subject>Structure-Activity Relationship</subject><subject>Water - chemistry</subject><subject>Water-soluble respiratory syncytial virus inhibitors</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEGL1TAQx4Mo7tvVL-BBctFba9KkaSteZHFVWFBE0VtI0yk7j7zmmaSV7tUvbsp7sDdPkxl-85_wI-QFZyVnXL3Zl_3BurJirC45z7PuEdlxqWQhJKsfkx3rFCvaTv66IJcx7hnjkkn5lFxwJVRbCbEjf79BPGIwyYeVxnWya0Lj6IJhjnScI_qJ4nSHPWYilvSrCYmKt_SnSRCK6N3cO6A9TPd4wMHce1dUhZ-ADhBwMQkXiPQPpjtqptzkS44au73SmoPzocU_I09G4yI8P9cr8uPmw_frT8Xtl4-fr9_fFlbyOhUj6-WgWDvwRrTMqlH1nA8jQCOzjla2XW8MqL5mAowdlDW25qNsRDNusBJX5PUp9xj87xli0geMFpwzE_g5at61om5rnsHqBNrgYwww6mPAgwmr5kxv6vVeb-r1pl5znmddXnp5Tp_7AwwPK2fXGXh1Bky0xo3BTBbjA9fUdVOJNnPvThxkFwtC0NEiTBYGDGCTHjz-7x__AAVhpW8</recordid><startdate>20060301</startdate><enddate>20060301</enddate><creator>Yu, Kuo-Long</creator><creator>Wang, Xiangdong Alan</creator><creator>Civiello, Rita L.</creator><creator>Trehan, Ashok K.</creator><creator>Pearce, Bradley C.</creator><creator>Yin, Zhiwei</creator><creator>Combrink, Keith D.</creator><creator>Gulgeze, H. 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Belgin</au><au>Zhang, Yi</au><au>Kadow, Kathleen F.</au><au>Cianci, Christopher W.</au><au>Clarke, Junius</au><au>Genovesi, Eugene V.</au><au>Medina, Ivette</au><au>Lamb, Lucinda</au><au>Wyde, Philip R.</au><au>Krystal, Mark</au><au>Meanwell, Nicholas A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Respiratory syncytial virus fusion inhibitors. Part 3: Water-soluble benzimidazol-2-one derivatives with antiviral activity in vivo</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2006-03-01</date><risdate>2006</risdate><volume>16</volume><issue>5</issue><spage>1115</spage><epage>1122</epage><pages>1115-1122</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The introduction of acidic and basic functionality into the side chains R and R′ of respiratory syncytial virus (RSV) fusion inhibitors
2 was examined in an effort to identify compounds suitable for evaluation in vivo in the cotton rat model of RSV infection following administration as a small particle aerosol. Several acid-containing compounds demonstrated potent antiviral activity in cell culture and exhibited efficacy in the cotton rat comparable to ribavirin. In a BALB/c mouse model, the amide
2aab reduced virus titers following oral dosing, establishing the potential of this class of RSV fusion inhibitors to interfere with infection in vivo following topical or systemic administration.
The introduction of acidic and basic functionality into the side chains of respiratory syncytial virus (RSV) fusion inhibitors was examined in an effort to identify compounds suitable for evaluation in vivo in the cotton rat model of RSV infection following administration as a small particle aerosol. The acidic compounds
2r,
2u,
2v,
2w,
2z, and
2aj demonstrated potent antiviral activity in cell culture and exhibited efficacy in the cotton rat comparable to ribavirin. In a BALB/c mouse model, the oxadiazolone
2aj reduced virus titers following subcutaneous dosing, whilst the ester
2az and amide
2aab exhibited efficacy following oral administration. These results established the potential of this class of RSV fusion inhibitors to interfere with infection in vivo following topical or systemic administration.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16368233</pmid><doi>10.1016/j.bmcl.2005.11.109</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2006-03, Vol.16 (5), p.1115-1122 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Amines - chemistry Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral Antiviral agents Antiviral Agents - adverse effects Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Benzimidazol-2-one derivatives Benzimidazoles - adverse effects Benzimidazoles - chemical synthesis Benzimidazoles - chemistry Benzimidazoles - pharmacology Biological and medical sciences Medical sciences Membrane Fusion - drug effects Mice Molecular Structure Pharmacology. Drug treatments Rats Respiratory syncytial virus Respiratory Syncytial Viruses - drug effects Respiratory Syncytial Viruses - physiology Sigmodontinae Solubility Structure-Activity Relationship Water - chemistry Water-soluble respiratory syncytial virus inhibitors |
| title | Respiratory syncytial virus fusion inhibitors. Part 3: Water-soluble benzimidazol-2-one derivatives with antiviral activity in vivo |
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