Synthesis and biological evaluation of 4-styrylcoumarin derivatives as inhibitors of TNF-α and IL-6 with anti-tubercular activity
A series of 4-styrylcoumarin have been synthesized by Knoevenagel condensation between substituted 4-methylcoumarin-3-carbonitrile and different heterocyclic or aromatic aldehydes. 4-Methylcoumarin-3-carbonitrile has been synthesized by the base catalyzed reaction between substituted 2-hydroxyacetop...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2011-04, Vol.21 (8), p.2547-2549 |
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| creator | Upadhyay, Kuldip Bavishi, Abhay Thakrar, Shailesh Radadiya, Ashish Vala, Hardevsinh Parekh, Shrey Bhavsar, Dhairya Savant, Mahesh Parmar, Manisha Adlakha, Priti Shah, Anamik |
| description | A series of 4-styrylcoumarin have been synthesized by Knoevenagel condensation between substituted 4-methylcoumarin-3-carbonitrile and different heterocyclic or aromatic aldehydes. 4-Methylcoumarin-3-carbonitrile has been synthesized by the base catalyzed reaction between substituted 2-hydroxyacetophenone and ethyl cyanoacetate. The structures of the newly synthesized compounds were confirmed by
1H NMR, IR and mass spectral analysis. All the compounds were evaluated for their anti-inflammatory activity (against TNF-α and IL-6) and anti-tubercular activity. Compounds
6a,
6h and
6j exhibited promising activity against IL-6 with 72–87% inhibition and compound
6v showed potent activity against TNF-α with 73% inhibition at 10
μM concentration. Whereas compounds
6n,
6o,
6r and
6u showed very good anti-tubercular activity against
Mycobacterium tuberculosis H37Rv strain at |
| doi_str_mv | 10.1016/j.bmcl.2011.02.016 |
| format | Article |
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1H NMR, IR and mass spectral analysis. All the compounds were evaluated for their anti-inflammatory activity (against TNF-α and IL-6) and anti-tubercular activity. Compounds
6a,
6h and
6j exhibited promising activity against IL-6 with 72–87% inhibition and compound
6v showed potent activity against TNF-α with 73% inhibition at 10
μM concentration. Whereas compounds
6n,
6o,
6r and
6u showed very good anti-tubercular activity against
Mycobacterium tuberculosis H37Rv strain at <6.25
μM.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2011.02.016</identifier><identifier>PMID: 21396814</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>4-Styrylcoumarin ; aldehydes ; Anti-inflammatory activity ; Anti-Inflammatory Agents - chemical synthesis ; Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - pharmacology ; Anti-tubercular ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antitubercular Agents - chemical synthesis ; Antitubercular Agents - chemistry ; Antitubercular Agents - pharmacology ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; condensation ; Coumarins - chemical synthesis ; Coumarins - chemistry ; Coumarins - pharmacology ; IL-6 ; interleukin-6 ; Interleukin-6 - antagonists & inhibitors ; Interleukin-6 - metabolism ; Medical sciences ; Microbial Sensitivity Tests ; Mycobacterium tuberculosis ; Mycobacterium tuberculosis - drug effects ; nuclear magnetic resonance spectroscopy ; Pharmacology. Drug treatments ; spectral analysis ; TNF-α ; tumor necrosis factor-alpha ; Tumor Necrosis Factor-alpha - antagonists & inhibitors ; Tumor Necrosis Factor-alpha - metabolism</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-04, Vol.21 (8), p.2547-2549</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c441t-b9ce4edebbd62b57997df043fcd746948aeb5784ad6400a6705fcaa2d2e90cfa3</citedby><cites>FETCH-LOGICAL-c441t-b9ce4edebbd62b57997df043fcd746948aeb5784ad6400a6705fcaa2d2e90cfa3</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.2011.02.016$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,45974</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24091108$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21396814$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Upadhyay, Kuldip</creatorcontrib><creatorcontrib>Bavishi, Abhay</creatorcontrib><creatorcontrib>Thakrar, Shailesh</creatorcontrib><creatorcontrib>Radadiya, Ashish</creatorcontrib><creatorcontrib>Vala, Hardevsinh</creatorcontrib><creatorcontrib>Parekh, Shrey</creatorcontrib><creatorcontrib>Bhavsar, Dhairya</creatorcontrib><creatorcontrib>Savant, Mahesh</creatorcontrib><creatorcontrib>Parmar, Manisha</creatorcontrib><creatorcontrib>Adlakha, Priti</creatorcontrib><creatorcontrib>Shah, Anamik</creatorcontrib><title>Synthesis and biological evaluation of 4-styrylcoumarin derivatives as inhibitors of TNF-α and IL-6 with anti-tubercular activity</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of 4-styrylcoumarin have been synthesized by Knoevenagel condensation between substituted 4-methylcoumarin-3-carbonitrile and different heterocyclic or aromatic aldehydes. 4-Methylcoumarin-3-carbonitrile has been synthesized by the base catalyzed reaction between substituted 2-hydroxyacetophenone and ethyl cyanoacetate. The structures of the newly synthesized compounds were confirmed by
1H NMR, IR and mass spectral analysis. All the compounds were evaluated for their anti-inflammatory activity (against TNF-α and IL-6) and anti-tubercular activity. Compounds
6a,
6h and
6j exhibited promising activity against IL-6 with 72–87% inhibition and compound
6v showed potent activity against TNF-α with 73% inhibition at 10
μM concentration. Whereas compounds
6n,
6o,
6r and
6u showed very good anti-tubercular activity against
Mycobacterium tuberculosis H37Rv strain at <6.25
μM.</description><subject>4-Styrylcoumarin</subject><subject>aldehydes</subject><subject>Anti-inflammatory activity</subject><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Anti-tubercular</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antitubercular Agents - chemical synthesis</subject><subject>Antitubercular Agents - chemistry</subject><subject>Antitubercular Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>condensation</subject><subject>Coumarins - chemical synthesis</subject><subject>Coumarins - chemistry</subject><subject>Coumarins - pharmacology</subject><subject>IL-6</subject><subject>interleukin-6</subject><subject>Interleukin-6 - antagonists & inhibitors</subject><subject>Interleukin-6 - metabolism</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Mycobacterium tuberculosis</subject><subject>Mycobacterium tuberculosis - drug effects</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Pharmacology. Drug treatments</subject><subject>spectral analysis</subject><subject>TNF-α</subject><subject>tumor necrosis factor-alpha</subject><subject>Tumor Necrosis Factor-alpha - antagonists & inhibitors</subject><subject>Tumor Necrosis Factor-alpha - metabolism</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcFu1DAURS0EokPhB1hANqirhOfEcWKJTVVRqDSCRVuJneXYLx2PMnGxnUHZ8kf9Eb4JhxlgByvLz-feZ91LyEsKBQXK326LbqeHogRKCyiLNHpEVpRxllcM6sdkBYJD3gr25YQ8C2ELQBkw9pSclLQSvKVsRb5fz2PcYLAhU6PJOusGd2e1GjLcq2FS0boxc33G8hBnPw_aTTvl7ZgZ9HafnveYlCGz48Z2NjofFvrm02X-4-GX49U659k3GzfpFm0epw69ngblM6WT2sb5OXnSqyHgi-N5Sm4v399cfMzXnz9cXZyvc80YjXknNDI02HWGl13dCNGYHljVa9MwLlirME1bpgxnAIo3UPdaqdKUKED3qjolZwffe---Thii3NmgcRjUiG4Ksm2WWNqy_j_JgTataGkiywOpvQvBYy_vvU0BzZKCXEqSW7mUJJeSJJQyjZLo1dF-6nZo_kh-t5KAN0dAhVRF79WobfjLMRCUQpu41weuV06qO5-Y2-u0qU5NV0smiXh3IDAFu7foZdAWR43GetRRGmf_9dOfgV28CQ</recordid><startdate>20110415</startdate><enddate>20110415</enddate><creator>Upadhyay, Kuldip</creator><creator>Bavishi, Abhay</creator><creator>Thakrar, Shailesh</creator><creator>Radadiya, Ashish</creator><creator>Vala, Hardevsinh</creator><creator>Parekh, Shrey</creator><creator>Bhavsar, Dhairya</creator><creator>Savant, Mahesh</creator><creator>Parmar, Manisha</creator><creator>Adlakha, Priti</creator><creator>Shah, Anamik</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><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><scope>7QL</scope><scope>7QO</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20110415</creationdate><title>Synthesis and biological evaluation of 4-styrylcoumarin derivatives as inhibitors of TNF-α and IL-6 with anti-tubercular activity</title><author>Upadhyay, Kuldip ; Bavishi, Abhay ; Thakrar, Shailesh ; Radadiya, Ashish ; Vala, Hardevsinh ; Parekh, Shrey ; Bhavsar, Dhairya ; Savant, Mahesh ; Parmar, Manisha ; Adlakha, Priti ; Shah, Anamik</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c441t-b9ce4edebbd62b57997df043fcd746948aeb5784ad6400a6705fcaa2d2e90cfa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>4-Styrylcoumarin</topic><topic>aldehydes</topic><topic>Anti-inflammatory activity</topic><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Anti-Inflammatory Agents - chemistry</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Anti-tubercular</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antitubercular Agents - chemical synthesis</topic><topic>Antitubercular Agents - chemistry</topic><topic>Antitubercular Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>condensation</topic><topic>Coumarins - chemical synthesis</topic><topic>Coumarins - chemistry</topic><topic>Coumarins - pharmacology</topic><topic>IL-6</topic><topic>interleukin-6</topic><topic>Interleukin-6 - antagonists & inhibitors</topic><topic>Interleukin-6 - metabolism</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Mycobacterium tuberculosis</topic><topic>Mycobacterium tuberculosis - drug effects</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Pharmacology. Drug treatments</topic><topic>spectral analysis</topic><topic>TNF-α</topic><topic>tumor necrosis factor-alpha</topic><topic>Tumor Necrosis Factor-alpha - antagonists & inhibitors</topic><topic>Tumor Necrosis Factor-alpha - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Upadhyay, Kuldip</creatorcontrib><creatorcontrib>Bavishi, Abhay</creatorcontrib><creatorcontrib>Thakrar, Shailesh</creatorcontrib><creatorcontrib>Radadiya, Ashish</creatorcontrib><creatorcontrib>Vala, Hardevsinh</creatorcontrib><creatorcontrib>Parekh, Shrey</creatorcontrib><creatorcontrib>Bhavsar, Dhairya</creatorcontrib><creatorcontrib>Savant, Mahesh</creatorcontrib><creatorcontrib>Parmar, Manisha</creatorcontrib><creatorcontrib>Adlakha, Priti</creatorcontrib><creatorcontrib>Shah, Anamik</creatorcontrib><collection>AGRIS</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>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Upadhyay, Kuldip</au><au>Bavishi, Abhay</au><au>Thakrar, Shailesh</au><au>Radadiya, Ashish</au><au>Vala, Hardevsinh</au><au>Parekh, Shrey</au><au>Bhavsar, Dhairya</au><au>Savant, Mahesh</au><au>Parmar, Manisha</au><au>Adlakha, Priti</au><au>Shah, Anamik</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological evaluation of 4-styrylcoumarin derivatives as inhibitors of TNF-α and IL-6 with anti-tubercular activity</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2011-04-15</date><risdate>2011</risdate><volume>21</volume><issue>8</issue><spage>2547</spage><epage>2549</epage><pages>2547-2549</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of 4-styrylcoumarin have been synthesized by Knoevenagel condensation between substituted 4-methylcoumarin-3-carbonitrile and different heterocyclic or aromatic aldehydes. 4-Methylcoumarin-3-carbonitrile has been synthesized by the base catalyzed reaction between substituted 2-hydroxyacetophenone and ethyl cyanoacetate. The structures of the newly synthesized compounds were confirmed by
1H NMR, IR and mass spectral analysis. All the compounds were evaluated for their anti-inflammatory activity (against TNF-α and IL-6) and anti-tubercular activity. Compounds
6a,
6h and
6j exhibited promising activity against IL-6 with 72–87% inhibition and compound
6v showed potent activity against TNF-α with 73% inhibition at 10
μM concentration. Whereas compounds
6n,
6o,
6r and
6u showed very good anti-tubercular activity against
Mycobacterium tuberculosis H37Rv strain at <6.25
μM.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21396814</pmid><doi>10.1016/j.bmcl.2011.02.016</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2011-04, Vol.21 (8), p.2547-2549 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | 4-Styrylcoumarin aldehydes Anti-inflammatory activity Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - pharmacology Anti-tubercular Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Antitubercular Agents - chemical synthesis Antitubercular Agents - chemistry Antitubercular Agents - pharmacology Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents condensation Coumarins - chemical synthesis Coumarins - chemistry Coumarins - pharmacology IL-6 interleukin-6 Interleukin-6 - antagonists & inhibitors Interleukin-6 - metabolism Medical sciences Microbial Sensitivity Tests Mycobacterium tuberculosis Mycobacterium tuberculosis - drug effects nuclear magnetic resonance spectroscopy Pharmacology. Drug treatments spectral analysis TNF-α tumor necrosis factor-alpha Tumor Necrosis Factor-alpha - antagonists & inhibitors Tumor Necrosis Factor-alpha - metabolism |
| title | Synthesis and biological evaluation of 4-styrylcoumarin derivatives as inhibitors of TNF-α and IL-6 with anti-tubercular activity |
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