Celecoxib analogs possessing a N-(4-nitrooxybutyl)piperidin-4-yl or N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridin-4-yl nitric oxide donor moiety: Synthesis, biological evaluation and nitric oxide release studies
A new group of hybrid nitric oxide (NO) releasing anti-inflammatory (AI) coxib prodrugs (NO-coxibs) wherein the para-tolyl moiety present in celecoxib was replaced by a N-(4-nitrooxybutyl)piperidyl 15a– b, or N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridyl 17a– b, NO-donor moiety was synthesized. All...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2010-02, Vol.20 (4), p.1324-1329 |
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| creator | Chowdhury, Morshed A. Abdellatif, Khaled R.A. Dong, Ying Yu, Gang Huang, Zhangjian Rahman, Moshfiqur Das, Dipankar Velázquez, Carlos A. Suresh, Mavanur R. Knaus, Edward E. |
| description | A new group of hybrid nitric oxide (NO) releasing anti-inflammatory (AI) coxib prodrugs (NO-coxibs) wherein the
para-tolyl moiety present in celecoxib was replaced by a
N-(4-nitrooxybutyl)piperidyl
15a–
b, or
N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridyl
17a–
b, NO-donor moiety was synthesized. All compounds released a low amount of NO upon incubation with phosphate buffered saline (PBS) at pH 7.4 (2.4–5.8% range). In comparison, the percentage NO released was higher (3.1–8.4% range) when these nitrate prodrugs were incubated in the presence of
l-cysteine. In vitro COX-1/COX-2 isozyme inhibition studies showed this group of compounds are moderately more potent, and hence selective, inhibitors of the COX-2 relative to the COX-1 enzyme. AI structure–activity relationship data acquired showed that compounds having a MeSO
2 COX-2 pharmacophore exhibited superior AI activity compared to analogs having a H
2NSO
2 substituent. Compounds having a MeSO
2 COX-2 pharmacophore in conjunction with a
N-(4-nitrooxybutyl)piperidyl (ED
50
=
132.4
mg/kg po), or a
N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridyl (ED
50
=
118.4
mg/kg po), moiety exhibited an AI potency profile that is similar to aspirin (ED
50
=
128.7
mg/kg po) but lower than ibuprofen (ED
50
=
67.4
mg/kg po). |
| doi_str_mv | 10.1016/j.bmcl.2010.01.014 |
| format | Article |
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para-tolyl moiety present in celecoxib was replaced by a
N-(4-nitrooxybutyl)piperidyl
15a–
b, or
N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridyl
17a–
b, NO-donor moiety was synthesized. All compounds released a low amount of NO upon incubation with phosphate buffered saline (PBS) at pH 7.4 (2.4–5.8% range). In comparison, the percentage NO released was higher (3.1–8.4% range) when these nitrate prodrugs were incubated in the presence of
l-cysteine. In vitro COX-1/COX-2 isozyme inhibition studies showed this group of compounds are moderately more potent, and hence selective, inhibitors of the COX-2 relative to the COX-1 enzyme. AI structure–activity relationship data acquired showed that compounds having a MeSO
2 COX-2 pharmacophore exhibited superior AI activity compared to analogs having a H
2NSO
2 substituent. Compounds having a MeSO
2 COX-2 pharmacophore in conjunction with a
N-(4-nitrooxybutyl)piperidyl (ED
50
=
132.4
mg/kg po), or a
N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridyl (ED
50
=
118.4
mg/kg po), moiety exhibited an AI potency profile that is similar to aspirin (ED
50
=
128.7
mg/kg po) but lower than ibuprofen (ED
50
=
67.4
mg/kg po).</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2010.01.014</identifier><identifier>PMID: 20097072</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>1,2,3,6-Tetrahydropyridine ; Animals ; Anti-inflammatory activity ; Anti-Inflammatory Agents - chemical synthesis ; Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - pharmacology ; Aspirin - pharmacology ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Celecoxib ; Crystallography, X-Ray ; Cyclooxygenase 2 Inhibitors - chemistry ; Cyclooxygenase-1 and cyclooxygenase-2 inhibition ; Humans ; Hydrogen-Ion Concentration ; Ibuprofen - pharmacology ; Inhibitory Concentration 50 ; Medical sciences ; Molecular Structure ; Nitrate prodrugs ; Nitric Oxide - chemistry ; Nitric Oxide Donors - chemical synthesis ; Nitric Oxide Donors - chemistry ; Nitric Oxide Donors - pharmacology ; Pharmacology. Drug treatments ; Piperidine ; Piperidines - chemical synthesis ; Piperidines - chemistry ; Piperidines - pharmacology ; Prodrugs - chemical synthesis ; Prodrugs - chemistry ; Prodrugs - pharmacology ; Pyrazoles - chemistry ; Rats ; Sheep ; Structure-Activity Relationship ; Sulfonamides - chemistry</subject><ispartof>Bioorganic & medicinal chemistry letters, 2010-02, Vol.20 (4), p.1324-1329</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c385t-ed2cee2fec3da3f7fbfb162ca1b879eb52897871eecd6e370c0100e0d39cdc073</citedby><cites>FETCH-LOGICAL-c385t-ed2cee2fec3da3f7fbfb162ca1b879eb52897871eecd6e370c0100e0d39cdc073</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X10000168$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22824693$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20097072$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chowdhury, Morshed A.</creatorcontrib><creatorcontrib>Abdellatif, Khaled R.A.</creatorcontrib><creatorcontrib>Dong, Ying</creatorcontrib><creatorcontrib>Yu, Gang</creatorcontrib><creatorcontrib>Huang, Zhangjian</creatorcontrib><creatorcontrib>Rahman, Moshfiqur</creatorcontrib><creatorcontrib>Das, Dipankar</creatorcontrib><creatorcontrib>Velázquez, Carlos A.</creatorcontrib><creatorcontrib>Suresh, Mavanur R.</creatorcontrib><creatorcontrib>Knaus, Edward E.</creatorcontrib><title>Celecoxib analogs possessing a N-(4-nitrooxybutyl)piperidin-4-yl or N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridin-4-yl nitric oxide donor moiety: Synthesis, biological evaluation and nitric oxide release studies</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A new group of hybrid nitric oxide (NO) releasing anti-inflammatory (AI) coxib prodrugs (NO-coxibs) wherein the
para-tolyl moiety present in celecoxib was replaced by a
N-(4-nitrooxybutyl)piperidyl
15a–
b, or
N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridyl
17a–
b, NO-donor moiety was synthesized. All compounds released a low amount of NO upon incubation with phosphate buffered saline (PBS) at pH 7.4 (2.4–5.8% range). In comparison, the percentage NO released was higher (3.1–8.4% range) when these nitrate prodrugs were incubated in the presence of
l-cysteine. In vitro COX-1/COX-2 isozyme inhibition studies showed this group of compounds are moderately more potent, and hence selective, inhibitors of the COX-2 relative to the COX-1 enzyme. AI structure–activity relationship data acquired showed that compounds having a MeSO
2 COX-2 pharmacophore exhibited superior AI activity compared to analogs having a H
2NSO
2 substituent. Compounds having a MeSO
2 COX-2 pharmacophore in conjunction with a
N-(4-nitrooxybutyl)piperidyl (ED
50
=
132.4
mg/kg po), or a
N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridyl (ED
50
=
118.4
mg/kg po), moiety exhibited an AI potency profile that is similar to aspirin (ED
50
=
128.7
mg/kg po) but lower than ibuprofen (ED
50
=
67.4
mg/kg po).</description><subject>1,2,3,6-Tetrahydropyridine</subject><subject>Animals</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>Aspirin - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Celecoxib</subject><subject>Crystallography, X-Ray</subject><subject>Cyclooxygenase 2 Inhibitors - chemistry</subject><subject>Cyclooxygenase-1 and cyclooxygenase-2 inhibition</subject><subject>Humans</subject><subject>Hydrogen-Ion Concentration</subject><subject>Ibuprofen - pharmacology</subject><subject>Inhibitory Concentration 50</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Nitrate prodrugs</subject><subject>Nitric Oxide - chemistry</subject><subject>Nitric Oxide Donors - chemical synthesis</subject><subject>Nitric Oxide Donors - chemistry</subject><subject>Nitric Oxide Donors - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperidine</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - chemistry</subject><subject>Piperidines - pharmacology</subject><subject>Prodrugs - chemical synthesis</subject><subject>Prodrugs - chemistry</subject><subject>Prodrugs - pharmacology</subject><subject>Pyrazoles - chemistry</subject><subject>Rats</subject><subject>Sheep</subject><subject>Structure-Activity Relationship</subject><subject>Sulfonamides - chemistry</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUuLFDEUhYMoTjv6B1xINqJCp82r6yFupPEFgy5UcBdSya2ZNKlKmaSGqd_pHzJNty8Q4UIgfOfm5ByEHjK6YZRVz_ebbjB-w2m5oKyMvIVWTFaSCEm3t9GKthUlTSu_nqF7Ke1pIaiUd9EZp7Stac1X6PsOPJhw4zqsR-3DZcJTSAlScuMl1vgDeSrJ6HIM4Wbp5rz4Z5ObIDrrRiLJ4nGI_4IIW_O1WFckQ476arExTMsfqgPtDC4PW8A2jGXLEBzk5QX-tIz5CpJLa9y5UCw5oz2Ga-1nnV0Yi1H7tz6WP-gEOOXZOkj30Z1e-wQPTuc5-vLm9efdO3Lx8e373asLYkSzzQQsNwC8ByOsFn3dd33HKm4065q6hW7Lm7ZuagZgbAWipqYETYFa0RpraC3O0ZPj3imGbzOkrAaXDHivRwhzUrUQrJTDq0LyI2liCTdCr6boBh0Xxag6dKn26tClOnSpKCsji-jRaf3cDWB_SX6WV4DHJ0CnElEf9Whc-s3xhsuqFYV7eeSghHHtIKpkHIwGrItgsrLB_c_HD4AOwgk</recordid><startdate>20100215</startdate><enddate>20100215</enddate><creator>Chowdhury, Morshed A.</creator><creator>Abdellatif, Khaled R.A.</creator><creator>Dong, Ying</creator><creator>Yu, Gang</creator><creator>Huang, Zhangjian</creator><creator>Rahman, Moshfiqur</creator><creator>Das, Dipankar</creator><creator>Velázquez, Carlos A.</creator><creator>Suresh, Mavanur R.</creator><creator>Knaus, Edward E.</creator><general>Elsevier Ltd</general><general>Elsevier</general><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></search><sort><creationdate>20100215</creationdate><title>Celecoxib analogs possessing a N-(4-nitrooxybutyl)piperidin-4-yl or N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridin-4-yl nitric oxide donor moiety: Synthesis, biological evaluation and nitric oxide release studies</title><author>Chowdhury, Morshed A. ; Abdellatif, Khaled R.A. ; Dong, Ying ; Yu, Gang ; Huang, Zhangjian ; Rahman, Moshfiqur ; Das, Dipankar ; Velázquez, Carlos A. ; Suresh, Mavanur R. ; Knaus, Edward E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c385t-ed2cee2fec3da3f7fbfb162ca1b879eb52897871eecd6e370c0100e0d39cdc073</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>1,2,3,6-Tetrahydropyridine</topic><topic>Animals</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>Aspirin - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Celecoxib</topic><topic>Crystallography, X-Ray</topic><topic>Cyclooxygenase 2 Inhibitors - chemistry</topic><topic>Cyclooxygenase-1 and cyclooxygenase-2 inhibition</topic><topic>Humans</topic><topic>Hydrogen-Ion Concentration</topic><topic>Ibuprofen - pharmacology</topic><topic>Inhibitory Concentration 50</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Nitrate prodrugs</topic><topic>Nitric Oxide - chemistry</topic><topic>Nitric Oxide Donors - chemical synthesis</topic><topic>Nitric Oxide Donors - chemistry</topic><topic>Nitric Oxide Donors - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperidine</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - chemistry</topic><topic>Piperidines - pharmacology</topic><topic>Prodrugs - chemical synthesis</topic><topic>Prodrugs - chemistry</topic><topic>Prodrugs - pharmacology</topic><topic>Pyrazoles - chemistry</topic><topic>Rats</topic><topic>Sheep</topic><topic>Structure-Activity Relationship</topic><topic>Sulfonamides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chowdhury, Morshed A.</creatorcontrib><creatorcontrib>Abdellatif, Khaled R.A.</creatorcontrib><creatorcontrib>Dong, Ying</creatorcontrib><creatorcontrib>Yu, Gang</creatorcontrib><creatorcontrib>Huang, Zhangjian</creatorcontrib><creatorcontrib>Rahman, Moshfiqur</creatorcontrib><creatorcontrib>Das, Dipankar</creatorcontrib><creatorcontrib>Velázquez, Carlos A.</creatorcontrib><creatorcontrib>Suresh, Mavanur R.</creatorcontrib><creatorcontrib>Knaus, Edward E.</creatorcontrib><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><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chowdhury, Morshed A.</au><au>Abdellatif, Khaled R.A.</au><au>Dong, Ying</au><au>Yu, Gang</au><au>Huang, Zhangjian</au><au>Rahman, Moshfiqur</au><au>Das, Dipankar</au><au>Velázquez, Carlos A.</au><au>Suresh, Mavanur R.</au><au>Knaus, Edward E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Celecoxib analogs possessing a N-(4-nitrooxybutyl)piperidin-4-yl or N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridin-4-yl nitric oxide donor moiety: Synthesis, biological evaluation and nitric oxide release studies</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2010-02-15</date><risdate>2010</risdate><volume>20</volume><issue>4</issue><spage>1324</spage><epage>1329</epage><pages>1324-1329</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A new group of hybrid nitric oxide (NO) releasing anti-inflammatory (AI) coxib prodrugs (NO-coxibs) wherein the
para-tolyl moiety present in celecoxib was replaced by a
N-(4-nitrooxybutyl)piperidyl
15a–
b, or
N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridyl
17a–
b, NO-donor moiety was synthesized. All compounds released a low amount of NO upon incubation with phosphate buffered saline (PBS) at pH 7.4 (2.4–5.8% range). In comparison, the percentage NO released was higher (3.1–8.4% range) when these nitrate prodrugs were incubated in the presence of
l-cysteine. In vitro COX-1/COX-2 isozyme inhibition studies showed this group of compounds are moderately more potent, and hence selective, inhibitors of the COX-2 relative to the COX-1 enzyme. AI structure–activity relationship data acquired showed that compounds having a MeSO
2 COX-2 pharmacophore exhibited superior AI activity compared to analogs having a H
2NSO
2 substituent. Compounds having a MeSO
2 COX-2 pharmacophore in conjunction with a
N-(4-nitrooxybutyl)piperidyl (ED
50
=
132.4
mg/kg po), or a
N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridyl (ED
50
=
118.4
mg/kg po), moiety exhibited an AI potency profile that is similar to aspirin (ED
50
=
128.7
mg/kg po) but lower than ibuprofen (ED
50
=
67.4
mg/kg po).</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20097072</pmid><doi>10.1016/j.bmcl.2010.01.014</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2010-02, Vol.20 (4), p.1324-1329 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_733120126 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | 1,2,3,6-Tetrahydropyridine Animals Anti-inflammatory activity Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - pharmacology Aspirin - pharmacology Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Celecoxib Crystallography, X-Ray Cyclooxygenase 2 Inhibitors - chemistry Cyclooxygenase-1 and cyclooxygenase-2 inhibition Humans Hydrogen-Ion Concentration Ibuprofen - pharmacology Inhibitory Concentration 50 Medical sciences Molecular Structure Nitrate prodrugs Nitric Oxide - chemistry Nitric Oxide Donors - chemical synthesis Nitric Oxide Donors - chemistry Nitric Oxide Donors - pharmacology Pharmacology. Drug treatments Piperidine Piperidines - chemical synthesis Piperidines - chemistry Piperidines - pharmacology Prodrugs - chemical synthesis Prodrugs - chemistry Prodrugs - pharmacology Pyrazoles - chemistry Rats Sheep Structure-Activity Relationship Sulfonamides - chemistry |
| title | Celecoxib analogs possessing a N-(4-nitrooxybutyl)piperidin-4-yl or N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridin-4-yl nitric oxide donor moiety: Synthesis, biological evaluation and nitric oxide release studies |
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