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Synthesis and evaluation of 1,5-diaryl-substituted tetrazoles as novel selective cyclooxygenase-2 (COX-2) inhibitors
A series of 1,5-diaryl-substituted tetrazole derivatives was synthesized. All compounds were evaluated in in vitro cyclooxygenase (COX) assays to determine COX-1 and COX-2 inhibitory potency and selectivity. A series of 1,5-diaryl-substituted tetrazole derivatives was synthesized via conversion of r...
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| Published in: | Bioorganic & medicinal chemistry letters 2011-03, Vol.21 (6), p.1823-1826 |
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| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c507t-e9fb251f71af1c886c7db9e143f8f09ff08f41f0e3714d640eba561198233f743 |
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| cites | cdi_FETCH-LOGICAL-c507t-e9fb251f71af1c886c7db9e143f8f09ff08f41f0e3714d640eba561198233f743 |
| container_end_page | 1826 |
| container_issue | 6 |
| container_start_page | 1823 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 21 |
| creator | Al-Hourani, Baker Jawabrah Sharma, Sai Kiran Mane, Jonathan Y. Tuszynski, Jack Baracos, Vickie Kniess, Torsten Suresh, Mavanur Pietzsch, Jens Wuest, Frank |
| description | A series of 1,5-diaryl-substituted tetrazole derivatives was synthesized. All compounds were evaluated in in vitro cyclooxygenase (COX) assays to determine COX-1 and COX-2 inhibitory potency and selectivity.
A series of 1,5-diaryl-substituted tetrazole derivatives was synthesized via conversion of readily available diaryl amides into corresponding imidoylchlorides followed by reaction with sodium azide. All compounds were evaluated by cyclooxygenase (COX) assays in vitro to determine COX-1 and COX-2 inhibitory potency and selectivity. Tetrazoles
3a–
e showed IC
50 values ranging from 0.42 to 8.1
mM for COX-1 and 2.0 to 200
μM for COX-2. Most potent compound
3c (IC
50 (COX-2)
=
2.0
μM) was further used in molecular modeling docking studies. |
| doi_str_mv | 10.1016/j.bmcl.2011.01.057 |
| format | article |
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A series of 1,5-diaryl-substituted tetrazole derivatives was synthesized via conversion of readily available diaryl amides into corresponding imidoylchlorides followed by reaction with sodium azide. All compounds were evaluated by cyclooxygenase (COX) assays in vitro to determine COX-1 and COX-2 inhibitory potency and selectivity. Tetrazoles
3a–
e showed IC
50 values ranging from 0.42 to 8.1
mM for COX-1 and 2.0 to 200
μM for COX-2. Most potent compound
3c (IC
50 (COX-2)
=
2.0
μM) was further used in molecular modeling docking studies.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2011.01.057</identifier><identifier>PMID: 21316237</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>1,5-Diaryl-tetrazoles ; amides ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; COX-2 inhibitors ; Cyclooxygenase ; Cyclooxygenase 2 Inhibitors - chemical synthesis ; Cyclooxygenase 2 Inhibitors - chemistry ; Cyclooxygenase 2 Inhibitors - pharmacology ; Drug Evaluation, Preclinical ; Hydrogen Bonding ; in vitro studies ; inhibitory concentration 50 ; Medical sciences ; Models, Molecular ; Pharmacology. Drug treatments ; prostaglandin synthase ; sodium azide ; Tetrazoles - chemical synthesis ; Tetrazoles - chemistry ; Tetrazoles - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-03, Vol.21 (6), p.1823-1826</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-c507t-e9fb251f71af1c886c7db9e143f8f09ff08f41f0e3714d640eba561198233f743</citedby><cites>FETCH-LOGICAL-c507t-e9fb251f71af1c886c7db9e143f8f09ff08f41f0e3714d640eba561198233f743</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23965678$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21316237$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Al-Hourani, Baker Jawabrah</creatorcontrib><creatorcontrib>Sharma, Sai Kiran</creatorcontrib><creatorcontrib>Mane, Jonathan Y.</creatorcontrib><creatorcontrib>Tuszynski, Jack</creatorcontrib><creatorcontrib>Baracos, Vickie</creatorcontrib><creatorcontrib>Kniess, Torsten</creatorcontrib><creatorcontrib>Suresh, Mavanur</creatorcontrib><creatorcontrib>Pietzsch, Jens</creatorcontrib><creatorcontrib>Wuest, Frank</creatorcontrib><title>Synthesis and evaluation of 1,5-diaryl-substituted tetrazoles as novel selective cyclooxygenase-2 (COX-2) inhibitors</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of 1,5-diaryl-substituted tetrazole derivatives was synthesized. All compounds were evaluated in in vitro cyclooxygenase (COX) assays to determine COX-1 and COX-2 inhibitory potency and selectivity.
A series of 1,5-diaryl-substituted tetrazole derivatives was synthesized via conversion of readily available diaryl amides into corresponding imidoylchlorides followed by reaction with sodium azide. All compounds were evaluated by cyclooxygenase (COX) assays in vitro to determine COX-1 and COX-2 inhibitory potency and selectivity. Tetrazoles
3a–
e showed IC
50 values ranging from 0.42 to 8.1
mM for COX-1 and 2.0 to 200
μM for COX-2. Most potent compound
3c (IC
50 (COX-2)
=
2.0
μM) was further used in molecular modeling docking studies.</description><subject>1,5-Diaryl-tetrazoles</subject><subject>amides</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>COX-2 inhibitors</subject><subject>Cyclooxygenase</subject><subject>Cyclooxygenase 2 Inhibitors - chemical synthesis</subject><subject>Cyclooxygenase 2 Inhibitors - chemistry</subject><subject>Cyclooxygenase 2 Inhibitors - pharmacology</subject><subject>Drug Evaluation, Preclinical</subject><subject>Hydrogen Bonding</subject><subject>in vitro studies</subject><subject>inhibitory concentration 50</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Pharmacology. Drug treatments</subject><subject>prostaglandin synthase</subject><subject>sodium azide</subject><subject>Tetrazoles - chemical synthesis</subject><subject>Tetrazoles - chemistry</subject><subject>Tetrazoles - pharmacology</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkU2LFDEQhoMo7uzqH_CgfZFVsMdUOkl3gxcZ_IKFPawLewvpdGU3Q6azm6QHx19vhhn1plBQl-etKuoh5AXQJVCQ79fLYWP8klGAJS0l2kdkAVzyuuFUPCYL2ktadz2_OSGnKa0pBU45f0pOGDQgWdMuSL7aTfkOk0uVnsYKt9rPOrswVcFW8E7Uo9Nx5-s0Dym7PGccq4w56p_BY8mkagpb9FVCjya7LVZmZ3wIP3a3OOmENaverC5vava2ctOdG1wOMT0jT6z2CZ8f-xm5_vzp--prfXH55dvq40VtBG1zjb0dmADbgrZguk6adhx6BN7YztLeWtpZDpZi0wIfJac4aCEB-o41jW15c0bOD3PvY3iYMWW1ccmg93rCMCfV0xaEZD39L9kJ0QNlHRSSHUgTQ0oRrbqPblN-pICqvRa1Vnstaq9F0VKiLaGXx_HzsMHxT-S3hwK8PgI6Ge1t1JNx6S_X9FLItivcqwNndVD6Nhbm-qpsEsVtwwWXhfhwILA8duswqmQcTgZHF4shNQb3r0t_AThYtH8</recordid><startdate>20110315</startdate><enddate>20110315</enddate><creator>Al-Hourani, Baker Jawabrah</creator><creator>Sharma, Sai Kiran</creator><creator>Mane, Jonathan Y.</creator><creator>Tuszynski, Jack</creator><creator>Baracos, Vickie</creator><creator>Kniess, Torsten</creator><creator>Suresh, Mavanur</creator><creator>Pietzsch, Jens</creator><creator>Wuest, Frank</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20110315</creationdate><title>Synthesis and evaluation of 1,5-diaryl-substituted tetrazoles as novel selective cyclooxygenase-2 (COX-2) inhibitors</title><author>Al-Hourani, Baker Jawabrah ; Sharma, Sai Kiran ; Mane, Jonathan Y. ; Tuszynski, Jack ; Baracos, Vickie ; Kniess, Torsten ; Suresh, Mavanur ; Pietzsch, Jens ; Wuest, Frank</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c507t-e9fb251f71af1c886c7db9e143f8f09ff08f41f0e3714d640eba561198233f743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>1,5-Diaryl-tetrazoles</topic><topic>amides</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>COX-2 inhibitors</topic><topic>Cyclooxygenase</topic><topic>Cyclooxygenase 2 Inhibitors - chemical synthesis</topic><topic>Cyclooxygenase 2 Inhibitors - chemistry</topic><topic>Cyclooxygenase 2 Inhibitors - pharmacology</topic><topic>Drug Evaluation, Preclinical</topic><topic>Hydrogen Bonding</topic><topic>in vitro studies</topic><topic>inhibitory concentration 50</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Pharmacology. Drug treatments</topic><topic>prostaglandin synthase</topic><topic>sodium azide</topic><topic>Tetrazoles - chemical synthesis</topic><topic>Tetrazoles - chemistry</topic><topic>Tetrazoles - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Al-Hourani, Baker Jawabrah</creatorcontrib><creatorcontrib>Sharma, Sai Kiran</creatorcontrib><creatorcontrib>Mane, Jonathan Y.</creatorcontrib><creatorcontrib>Tuszynski, Jack</creatorcontrib><creatorcontrib>Baracos, Vickie</creatorcontrib><creatorcontrib>Kniess, Torsten</creatorcontrib><creatorcontrib>Suresh, Mavanur</creatorcontrib><creatorcontrib>Pietzsch, Jens</creatorcontrib><creatorcontrib>Wuest, Frank</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</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>Al-Hourani, Baker Jawabrah</au><au>Sharma, Sai Kiran</au><au>Mane, Jonathan Y.</au><au>Tuszynski, Jack</au><au>Baracos, Vickie</au><au>Kniess, Torsten</au><au>Suresh, Mavanur</au><au>Pietzsch, Jens</au><au>Wuest, Frank</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and evaluation of 1,5-diaryl-substituted tetrazoles as novel selective cyclooxygenase-2 (COX-2) inhibitors</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2011-03-15</date><risdate>2011</risdate><volume>21</volume><issue>6</issue><spage>1823</spage><epage>1826</epage><pages>1823-1826</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of 1,5-diaryl-substituted tetrazole derivatives was synthesized. All compounds were evaluated in in vitro cyclooxygenase (COX) assays to determine COX-1 and COX-2 inhibitory potency and selectivity.
A series of 1,5-diaryl-substituted tetrazole derivatives was synthesized via conversion of readily available diaryl amides into corresponding imidoylchlorides followed by reaction with sodium azide. All compounds were evaluated by cyclooxygenase (COX) assays in vitro to determine COX-1 and COX-2 inhibitory potency and selectivity. Tetrazoles
3a–
e showed IC
50 values ranging from 0.42 to 8.1
mM for COX-1 and 2.0 to 200
μM for COX-2. Most potent compound
3c (IC
50 (COX-2)
=
2.0
μM) was further used in molecular modeling docking studies.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21316237</pmid><doi>10.1016/j.bmcl.2011.01.057</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2011-03, Vol.21 (6), p.1823-1826 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | ScienceDirect Freedom Collection |
| subjects | 1,5-Diaryl-tetrazoles amides Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents COX-2 inhibitors Cyclooxygenase Cyclooxygenase 2 Inhibitors - chemical synthesis Cyclooxygenase 2 Inhibitors - chemistry Cyclooxygenase 2 Inhibitors - pharmacology Drug Evaluation, Preclinical Hydrogen Bonding in vitro studies inhibitory concentration 50 Medical sciences Models, Molecular Pharmacology. Drug treatments prostaglandin synthase sodium azide Tetrazoles - chemical synthesis Tetrazoles - chemistry Tetrazoles - pharmacology |
| title | Synthesis and evaluation of 1,5-diaryl-substituted tetrazoles as novel selective cyclooxygenase-2 (COX-2) inhibitors |
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