Visnagin and benzofuran scaffold-based molecules as selective cyclooxygenase-2 inhibitors with anti-inflammatory and analgesic properties: design, synthesis and molecular docking
A series of new visnagin and benzofuran scaffold-based molecules was designed and synthesized as anti-inflammatory and analgesic agents. Biological screening of these compounds showed that they exhibit potent anti-inflammatory/analgesic activity with a safer side effect profile in mouse models. cycl...
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| Veröffentlicht in: | Future medicinal chemistry 2019-04, Vol.11 (7), p.659-676 |
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| container_title | Future medicinal chemistry |
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| creator | Khalil, Hazem SA Sedky, Nada K Amin, Kamelia M Abd Elhafez, Omaima M Arafa, Reem K |
| description | A series of new visnagin and benzofuran scaffold-based molecules was designed and synthesized as anti-inflammatory and analgesic agents. Biological screening of these compounds showed that they exhibit potent anti-inflammatory/analgesic activity with a safer side effect profile in
mouse models.
cyclooxygenase (COX) inhibition assay showed that the compounds elicit their function through selective COX-2 inhibition. Molecular docking study also revealed the ability of the compounds to correctly recognize the active site and achieve noncovalent binding interactions with key residues therein. The best combined profile of anti-inflammatory, analgesic and COX-2 selective inhibition properties in association with low gastrotoxicity was displayed by the analogs 8, 11b and 19d, which can be considered as promising leads for further future optimization. |
| doi_str_mv | 10.4155/fmc-2018-0398 |
| format | Article |
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mouse models.
cyclooxygenase (COX) inhibition assay showed that the compounds elicit their function through selective COX-2 inhibition. Molecular docking study also revealed the ability of the compounds to correctly recognize the active site and achieve noncovalent binding interactions with key residues therein. The best combined profile of anti-inflammatory, analgesic and COX-2 selective inhibition properties in association with low gastrotoxicity was displayed by the analogs 8, 11b and 19d, which can be considered as promising leads for further future optimization.</description><identifier>ISSN: 1756-8919</identifier><identifier>EISSN: 1756-8927</identifier><identifier>DOI: 10.4155/fmc-2018-0398</identifier><identifier>PMID: 30958028</identifier><language>eng</language><publisher>England: Future Science Ltd</publisher><subject>Analgesics - chemistry ; Analgesics - pharmacology ; Animals ; Anti-Inflammatory Agents, Non-Steroidal - chemistry ; Anti-Inflammatory Agents, Non-Steroidal - pharmacology ; benzofuran ; Benzofurans - chemistry ; Benzofurans - pharmacology ; COX-2 selective inhibitors ; Cyclooxygenase 2 Inhibitors - chemistry ; Cyclooxygenase 2 Inhibitors - pharmacology ; Drug Evaluation, Preclinical ; Female ; Gastric Absorption ; Humans ; Khellin - chemistry ; Khellin - pharmacology ; Male ; Mice ; molecular docking ; Molecular Docking Simulation ; Molecular Structure ; Protein Binding ; Rats ; Structure-Activity Relationship ; ulcerogenicity ; visnagin</subject><ispartof>Future medicinal chemistry, 2019-04, Vol.11 (7), p.659-676</ispartof><rights>2019 Newlands Press</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c343t-8e8f650d04bf38252aa46255d8b41e36f26b1f470445958fe456a2b3a96e89e93</citedby><cites>FETCH-LOGICAL-c343t-8e8f650d04bf38252aa46255d8b41e36f26b1f470445958fe456a2b3a96e89e93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30958028$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Khalil, Hazem SA</creatorcontrib><creatorcontrib>Sedky, Nada K</creatorcontrib><creatorcontrib>Amin, Kamelia M</creatorcontrib><creatorcontrib>Abd Elhafez, Omaima M</creatorcontrib><creatorcontrib>Arafa, Reem K</creatorcontrib><title>Visnagin and benzofuran scaffold-based molecules as selective cyclooxygenase-2 inhibitors with anti-inflammatory and analgesic properties: design, synthesis and molecular docking</title><title>Future medicinal chemistry</title><addtitle>Future Med Chem</addtitle><description>A series of new visnagin and benzofuran scaffold-based molecules was designed and synthesized as anti-inflammatory and analgesic agents. Biological screening of these compounds showed that they exhibit potent anti-inflammatory/analgesic activity with a safer side effect profile in
mouse models.
cyclooxygenase (COX) inhibition assay showed that the compounds elicit their function through selective COX-2 inhibition. Molecular docking study also revealed the ability of the compounds to correctly recognize the active site and achieve noncovalent binding interactions with key residues therein. The best combined profile of anti-inflammatory, analgesic and COX-2 selective inhibition properties in association with low gastrotoxicity was displayed by the analogs 8, 11b and 19d, which can be considered as promising leads for further future optimization.</description><subject>Analgesics - chemistry</subject><subject>Analgesics - pharmacology</subject><subject>Animals</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemistry</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</subject><subject>benzofuran</subject><subject>Benzofurans - chemistry</subject><subject>Benzofurans - pharmacology</subject><subject>COX-2 selective inhibitors</subject><subject>Cyclooxygenase 2 Inhibitors - chemistry</subject><subject>Cyclooxygenase 2 Inhibitors - pharmacology</subject><subject>Drug Evaluation, Preclinical</subject><subject>Female</subject><subject>Gastric Absorption</subject><subject>Humans</subject><subject>Khellin - chemistry</subject><subject>Khellin - pharmacology</subject><subject>Male</subject><subject>Mice</subject><subject>molecular docking</subject><subject>Molecular Docking Simulation</subject><subject>Molecular Structure</subject><subject>Protein Binding</subject><subject>Rats</subject><subject>Structure-Activity Relationship</subject><subject>ulcerogenicity</subject><subject>visnagin</subject><issn>1756-8919</issn><issn>1756-8927</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kU1v1DAQhiMEolXbI1fkIwcMjj-yNjdUQUGqxKVwjRxnnDUk9uJJCuFn9RfW2116qy_zocfvjOatqlc1eydrpd77yVHOak2ZMPpZdVpvVEO14Zvnj3ltTqoLxJ-sPMG1adTL6kQwozTj-rS6-xEw2iFEYmNPOoj_kl-yjQSd9T6NPe0sQk-mNIJbRkBikSCUYg63QNzqxpT-rgPEglFOQtyGLswpI_kT5m1RnQMN0Y92mmxprw9zbLTjABgc2eW0gzwHwA-kL50hviW4xnlbcnxgj5NtJn1yv0IczqsX3o4IF8d4Vn3__Onm8gu9_nb19fLjNXVCiplq0L5RrGey80Jzxa2VDVeq152sQTSeN13t5YZJqco1PEjVWN4JaxrQBow4q94cdMuOvxfAuZ0COhhHGyEt2HLOlGR606iC0gPqckLM4NtdDpPNa1uzdu9UW5xq9061e6cK__oovXQT9I_0f18KYA6AX-YlA7oA0UF7qMqP4EKEJ8TvARxqpv8</recordid><startdate>20190401</startdate><startdate>20190401</startdate><enddate>20190401</enddate><enddate>20190401</enddate><creator>Khalil, Hazem SA</creator><creator>Sedky, Nada K</creator><creator>Amin, Kamelia M</creator><creator>Abd Elhafez, Omaima M</creator><creator>Arafa, Reem K</creator><general>Future Science 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>20190401</creationdate><title>Visnagin and benzofuran scaffold-based molecules as selective cyclooxygenase-2 inhibitors with anti-inflammatory and analgesic properties: design, synthesis and molecular docking</title><author>Khalil, Hazem SA ; Sedky, Nada K ; Amin, Kamelia M ; Abd Elhafez, Omaima M ; Arafa, Reem K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c343t-8e8f650d04bf38252aa46255d8b41e36f26b1f470445958fe456a2b3a96e89e93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Analgesics - chemistry</topic><topic>Analgesics - pharmacology</topic><topic>Animals</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemistry</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</topic><topic>benzofuran</topic><topic>Benzofurans - chemistry</topic><topic>Benzofurans - pharmacology</topic><topic>COX-2 selective inhibitors</topic><topic>Cyclooxygenase 2 Inhibitors - chemistry</topic><topic>Cyclooxygenase 2 Inhibitors - pharmacology</topic><topic>Drug Evaluation, Preclinical</topic><topic>Female</topic><topic>Gastric Absorption</topic><topic>Humans</topic><topic>Khellin - chemistry</topic><topic>Khellin - pharmacology</topic><topic>Male</topic><topic>Mice</topic><topic>molecular docking</topic><topic>Molecular Docking Simulation</topic><topic>Molecular Structure</topic><topic>Protein Binding</topic><topic>Rats</topic><topic>Structure-Activity Relationship</topic><topic>ulcerogenicity</topic><topic>visnagin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Khalil, Hazem SA</creatorcontrib><creatorcontrib>Sedky, Nada K</creatorcontrib><creatorcontrib>Amin, Kamelia M</creatorcontrib><creatorcontrib>Abd Elhafez, Omaima M</creatorcontrib><creatorcontrib>Arafa, Reem 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>Future medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Khalil, Hazem SA</au><au>Sedky, Nada K</au><au>Amin, Kamelia M</au><au>Abd Elhafez, Omaima M</au><au>Arafa, Reem K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visnagin and benzofuran scaffold-based molecules as selective cyclooxygenase-2 inhibitors with anti-inflammatory and analgesic properties: design, synthesis and molecular docking</atitle><jtitle>Future medicinal chemistry</jtitle><addtitle>Future Med Chem</addtitle><date>2019-04-01</date><date>2019-04-01</date><risdate>2019</risdate><risdate>2019</risdate><volume>11</volume><issue>7</issue><spage>659</spage><epage>676</epage><pages>659-676</pages><issn>1756-8919</issn><eissn>1756-8927</eissn><abstract>A series of new visnagin and benzofuran scaffold-based molecules was designed and synthesized as anti-inflammatory and analgesic agents. Biological screening of these compounds showed that they exhibit potent anti-inflammatory/analgesic activity with a safer side effect profile in
mouse models.
cyclooxygenase (COX) inhibition assay showed that the compounds elicit their function through selective COX-2 inhibition. Molecular docking study also revealed the ability of the compounds to correctly recognize the active site and achieve noncovalent binding interactions with key residues therein. The best combined profile of anti-inflammatory, analgesic and COX-2 selective inhibition properties in association with low gastrotoxicity was displayed by the analogs 8, 11b and 19d, which can be considered as promising leads for further future optimization.</abstract><cop>England</cop><pub>Future Science Ltd</pub><pmid>30958028</pmid><doi>10.4155/fmc-2018-0398</doi><tpages>18</tpages></addata></record> |
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| subjects | Analgesics - chemistry Analgesics - pharmacology Animals Anti-Inflammatory Agents, Non-Steroidal - chemistry Anti-Inflammatory Agents, Non-Steroidal - pharmacology benzofuran Benzofurans - chemistry Benzofurans - pharmacology COX-2 selective inhibitors Cyclooxygenase 2 Inhibitors - chemistry Cyclooxygenase 2 Inhibitors - pharmacology Drug Evaluation, Preclinical Female Gastric Absorption Humans Khellin - chemistry Khellin - pharmacology Male Mice molecular docking Molecular Docking Simulation Molecular Structure Protein Binding Rats Structure-Activity Relationship ulcerogenicity visnagin |
| title | Visnagin and benzofuran scaffold-based molecules as selective cyclooxygenase-2 inhibitors with anti-inflammatory and analgesic properties: design, synthesis and molecular docking |
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