Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity
[Display omitted] A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-[2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in M...
Gespeichert in:
| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2017-05, Vol.27 (10), p.2181-2184 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2184 |
|---|---|
| container_issue | 10 |
| container_start_page | 2181 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 27 |
| creator | Artyushin, Oleg I. Sharova, Elena V. Vinogradova, Natalya M. Genkina, Galina K. Moiseeva, Aleksandra A. Klemenkova, Zinaida S. Orshanskaya, Iana R. Shtro, Anna A. Kadyrova, Renata A. Zarubaev, Vladimir V. Yarovaya, Olga I. Salakhutdinov, Nariman F. Brel, Valery K. |
| description | [Display omitted]
A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-[2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells of the compounds obtained were performed. The structure-activity relationship analysis suggests that to possess virus-inhibiting activity, the compounds of this group should bear oxygen atom with a short linker (C2-C4), either as a hydroxyl group (18, 19, 29), keto-group (21) or as a part of a heterocycle (24). These compounds demonstrated low cytotoxicity along with high anti-viral activity. |
| doi_str_mv | 10.1016/j.bmcl.2017.03.051 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1883839016</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0960894X17303013</els_id><sourcerecordid>1883839016</sourcerecordid><originalsourceid>FETCH-LOGICAL-c356t-f2dfa4e8044577e8c832afbf9bcd0467bb73ecbd8afbd6ff706356e6213ce6623</originalsourceid><addsrcrecordid>eNp9kE2LFDEQhoMo7rj6BzxIjl66TTrpdAa8yOLHwoIHFbyFdKWyk9n-GJP0QP9708zqcU8Jxfs-VD2EvOWs5oyrD8e6H2GoG8a7momatfwZ2XGpZCUka5-THdsrVum9_H1FXqV0ZIxLJuVLctVooVQr2I48_FinfMAUEp09BTueDgg4IXUYw9nmcMZElxSmewpDgAcKBxxDynGlI-bD7OZhvl-pnRxNeXHrRim8EMuolEO0A7Ww_fL6mrzwdkj45vG9Jr--fP558626-_719ubTXQWiVbnyjfNWoi6rtl2HGrRorO_9vgfHpOr6vhMIvdNl6JT3HVOlh6rhAlCpRlyT9xfuKc5_FkzZlI0Bh8FOOC_JcK2FFvuisESbSxTinFJEb04xjDauhjOzSTZHs0k2m2TDhCmSS-ndI3_pR3T_K_-slsDHSwDLleeA0SQIOAG6EBGycXN4iv8XLwOQ_w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1883839016</pqid></control><display><type>article</type><title>Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity</title><source>MEDLINE</source><source>Access via ScienceDirect (Elsevier)</source><creator>Artyushin, Oleg I. ; Sharova, Elena V. ; Vinogradova, Natalya M. ; Genkina, Galina K. ; Moiseeva, Aleksandra A. ; Klemenkova, Zinaida S. ; Orshanskaya, Iana R. ; Shtro, Anna A. ; Kadyrova, Renata A. ; Zarubaev, Vladimir V. ; Yarovaya, Olga I. ; Salakhutdinov, Nariman F. ; Brel, Valery K.</creator><creatorcontrib>Artyushin, Oleg I. ; Sharova, Elena V. ; Vinogradova, Natalya M. ; Genkina, Galina K. ; Moiseeva, Aleksandra A. ; Klemenkova, Zinaida S. ; Orshanskaya, Iana R. ; Shtro, Anna A. ; Kadyrova, Renata A. ; Zarubaev, Vladimir V. ; Yarovaya, Olga I. ; Salakhutdinov, Nariman F. ; Brel, Valery K.</creatorcontrib><description>[Display omitted]
A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-[2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells of the compounds obtained were performed. The structure-activity relationship analysis suggests that to possess virus-inhibiting activity, the compounds of this group should bear oxygen atom with a short linker (C2-C4), either as a hydroxyl group (18, 19, 29), keto-group (21) or as a part of a heterocycle (24). These compounds demonstrated low cytotoxicity along with high anti-viral activity.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2017.03.051</identifier><identifier>PMID: 28366530</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Acetylenes ; Animals ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Antivirals ; Azides ; Camphor ; Camphor - analogs & derivatives ; Camphor - chemical synthesis ; Camphor - chemistry ; Camphor - pharmacology ; Click Chemistry ; Dogs ; Ethanolamines - chemical synthesis ; Ethanolamines - chemistry ; Ethanolamines - pharmacology ; Humans ; Imine derivatives ; Influenza ; Influenza A Virus, H1N1 Subtype - drug effects ; Madin Darby Canine Kidney Cells ; Structure-Activity Relationship ; Triazoles</subject><ispartof>Bioorganic & medicinal chemistry letters, 2017-05, Vol.27 (10), p.2181-2184</ispartof><rights>2017</rights><rights>Copyright © 2017. Published by Elsevier Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-f2dfa4e8044577e8c832afbf9bcd0467bb73ecbd8afbd6ff706356e6213ce6623</citedby><cites>FETCH-LOGICAL-c356t-f2dfa4e8044577e8c832afbf9bcd0467bb73ecbd8afbd6ff706356e6213ce6623</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2017.03.051$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27928,27929,45999</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28366530$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Artyushin, Oleg I.</creatorcontrib><creatorcontrib>Sharova, Elena V.</creatorcontrib><creatorcontrib>Vinogradova, Natalya M.</creatorcontrib><creatorcontrib>Genkina, Galina K.</creatorcontrib><creatorcontrib>Moiseeva, Aleksandra A.</creatorcontrib><creatorcontrib>Klemenkova, Zinaida S.</creatorcontrib><creatorcontrib>Orshanskaya, Iana R.</creatorcontrib><creatorcontrib>Shtro, Anna A.</creatorcontrib><creatorcontrib>Kadyrova, Renata A.</creatorcontrib><creatorcontrib>Zarubaev, Vladimir V.</creatorcontrib><creatorcontrib>Yarovaya, Olga I.</creatorcontrib><creatorcontrib>Salakhutdinov, Nariman F.</creatorcontrib><creatorcontrib>Brel, Valery K.</creatorcontrib><title>Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-[2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells of the compounds obtained were performed. The structure-activity relationship analysis suggests that to possess virus-inhibiting activity, the compounds of this group should bear oxygen atom with a short linker (C2-C4), either as a hydroxyl group (18, 19, 29), keto-group (21) or as a part of a heterocycle (24). These compounds demonstrated low cytotoxicity along with high anti-viral activity.</description><subject>Acetylenes</subject><subject>Animals</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Antivirals</subject><subject>Azides</subject><subject>Camphor</subject><subject>Camphor - analogs & derivatives</subject><subject>Camphor - chemical synthesis</subject><subject>Camphor - chemistry</subject><subject>Camphor - pharmacology</subject><subject>Click Chemistry</subject><subject>Dogs</subject><subject>Ethanolamines - chemical synthesis</subject><subject>Ethanolamines - chemistry</subject><subject>Ethanolamines - pharmacology</subject><subject>Humans</subject><subject>Imine derivatives</subject><subject>Influenza</subject><subject>Influenza A Virus, H1N1 Subtype - drug effects</subject><subject>Madin Darby Canine Kidney Cells</subject><subject>Structure-Activity Relationship</subject><subject>Triazoles</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE2LFDEQhoMo7rj6BzxIjl66TTrpdAa8yOLHwoIHFbyFdKWyk9n-GJP0QP9708zqcU8Jxfs-VD2EvOWs5oyrD8e6H2GoG8a7momatfwZ2XGpZCUka5-THdsrVum9_H1FXqV0ZIxLJuVLctVooVQr2I48_FinfMAUEp09BTueDgg4IXUYw9nmcMZElxSmewpDgAcKBxxDynGlI-bD7OZhvl-pnRxNeXHrRim8EMuolEO0A7Ww_fL6mrzwdkj45vG9Jr--fP558626-_719ubTXQWiVbnyjfNWoi6rtl2HGrRorO_9vgfHpOr6vhMIvdNl6JT3HVOlh6rhAlCpRlyT9xfuKc5_FkzZlI0Bh8FOOC_JcK2FFvuisESbSxTinFJEb04xjDauhjOzSTZHs0k2m2TDhCmSS-ndI3_pR3T_K_-slsDHSwDLleeA0SQIOAG6EBGycXN4iv8XLwOQ_w</recordid><startdate>20170515</startdate><enddate>20170515</enddate><creator>Artyushin, Oleg I.</creator><creator>Sharova, Elena V.</creator><creator>Vinogradova, Natalya M.</creator><creator>Genkina, Galina K.</creator><creator>Moiseeva, Aleksandra A.</creator><creator>Klemenkova, Zinaida S.</creator><creator>Orshanskaya, Iana R.</creator><creator>Shtro, Anna A.</creator><creator>Kadyrova, Renata A.</creator><creator>Zarubaev, Vladimir V.</creator><creator>Yarovaya, Olga I.</creator><creator>Salakhutdinov, Nariman F.</creator><creator>Brel, Valery K.</creator><general>Elsevier Ltd</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>7X8</scope></search><sort><creationdate>20170515</creationdate><title>Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity</title><author>Artyushin, Oleg I. ; Sharova, Elena V. ; Vinogradova, Natalya M. ; Genkina, Galina K. ; Moiseeva, Aleksandra A. ; Klemenkova, Zinaida S. ; Orshanskaya, Iana R. ; Shtro, Anna A. ; Kadyrova, Renata A. ; Zarubaev, Vladimir V. ; Yarovaya, Olga I. ; Salakhutdinov, Nariman F. ; Brel, Valery K.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-f2dfa4e8044577e8c832afbf9bcd0467bb73ecbd8afbd6ff706356e6213ce6623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acetylenes</topic><topic>Animals</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Antivirals</topic><topic>Azides</topic><topic>Camphor</topic><topic>Camphor - analogs & derivatives</topic><topic>Camphor - chemical synthesis</topic><topic>Camphor - chemistry</topic><topic>Camphor - pharmacology</topic><topic>Click Chemistry</topic><topic>Dogs</topic><topic>Ethanolamines - chemical synthesis</topic><topic>Ethanolamines - chemistry</topic><topic>Ethanolamines - pharmacology</topic><topic>Humans</topic><topic>Imine derivatives</topic><topic>Influenza</topic><topic>Influenza A Virus, H1N1 Subtype - drug effects</topic><topic>Madin Darby Canine Kidney Cells</topic><topic>Structure-Activity Relationship</topic><topic>Triazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Artyushin, Oleg I.</creatorcontrib><creatorcontrib>Sharova, Elena V.</creatorcontrib><creatorcontrib>Vinogradova, Natalya M.</creatorcontrib><creatorcontrib>Genkina, Galina K.</creatorcontrib><creatorcontrib>Moiseeva, Aleksandra A.</creatorcontrib><creatorcontrib>Klemenkova, Zinaida S.</creatorcontrib><creatorcontrib>Orshanskaya, Iana R.</creatorcontrib><creatorcontrib>Shtro, Anna A.</creatorcontrib><creatorcontrib>Kadyrova, Renata A.</creatorcontrib><creatorcontrib>Zarubaev, Vladimir V.</creatorcontrib><creatorcontrib>Yarovaya, Olga I.</creatorcontrib><creatorcontrib>Salakhutdinov, Nariman F.</creatorcontrib><creatorcontrib>Brel, Valery K.</creatorcontrib><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 letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Artyushin, Oleg I.</au><au>Sharova, Elena V.</au><au>Vinogradova, Natalya M.</au><au>Genkina, Galina K.</au><au>Moiseeva, Aleksandra A.</au><au>Klemenkova, Zinaida S.</au><au>Orshanskaya, Iana R.</au><au>Shtro, Anna A.</au><au>Kadyrova, Renata A.</au><au>Zarubaev, Vladimir V.</au><au>Yarovaya, Olga I.</au><au>Salakhutdinov, Nariman F.</au><au>Brel, Valery K.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2017-05-15</date><risdate>2017</risdate><volume>27</volume><issue>10</issue><spage>2181</spage><epage>2184</epage><pages>2181-2184</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-[2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells of the compounds obtained were performed. The structure-activity relationship analysis suggests that to possess virus-inhibiting activity, the compounds of this group should bear oxygen atom with a short linker (C2-C4), either as a hydroxyl group (18, 19, 29), keto-group (21) or as a part of a heterocycle (24). These compounds demonstrated low cytotoxicity along with high anti-viral activity.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>28366530</pmid><doi>10.1016/j.bmcl.2017.03.051</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2017-05, Vol.27 (10), p.2181-2184 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1883839016 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Acetylenes Animals Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Antivirals Azides Camphor Camphor - analogs & derivatives Camphor - chemical synthesis Camphor - chemistry Camphor - pharmacology Click Chemistry Dogs Ethanolamines - chemical synthesis Ethanolamines - chemistry Ethanolamines - pharmacology Humans Imine derivatives Influenza Influenza A Virus, H1N1 Subtype - drug effects Madin Darby Canine Kidney Cells Structure-Activity Relationship Triazoles |
| title | Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-16T22%3A56%3A11IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20camphecene%20derivatives%20using%20click%20chemistry%20methodology%20and%20study%20of%20their%20antiviral%20activity&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry%20letters&rft.au=Artyushin,%20Oleg%20I.&rft.date=2017-05-15&rft.volume=27&rft.issue=10&rft.spage=2181&rft.epage=2184&rft.pages=2181-2184&rft.issn=0960-894X&rft.eissn=1464-3405&rft_id=info:doi/10.1016/j.bmcl.2017.03.051&rft_dat=%3Cproquest_cross%3E1883839016%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1883839016&rft_id=info:pmid/28366530&rft_els_id=S0960894X17303013&rfr_iscdi=true |