Quaternary ammonium substituted thieno[3,2- e]-1,2-thiazine-6-sulfonamide 1,1-dioxides: Potential membrane-impermeable inhibitors of carbonic anhydrase
Thieno[3,2- e]-1,2-thiazine-6-sulfonamide 1,1-dioxides, which have a quaternary ammonium moiety incorporated into their structures, were synthesized. All of the quaternary ammonium salts prepared in the present study are potent inhibitors of both human carbonic anhydrase-II and recombinant human car...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2006-03, Vol.14 (6), p.2052-2059 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | May, Jesse A. Namil, Abdelmoula Chen, Hwang-Hsing Dantanarayana, Anura P. Dupré, Brian Liao, John C. |
| description | Thieno[3,2-
e]-1,2-thiazine-6-sulfonamide 1,1-dioxides, which have a quaternary ammonium moiety incorporated into their structures, were synthesized. All of the quaternary ammonium salts prepared in the present study are potent inhibitors of both human carbonic anhydrase-II and recombinant human carbonic anhydrase-IV; they are significantly more potent as inhibitors of these carbonic anhydrase isozymes than the previously reported inhibitor quaternary ammonium homosulfanilamide. By virtue of the permanent cationic charge on these compounds they are anticipated to be membrane-impermeable inhibitors of carbonic anhydrase. Spiro quaternary ammonium compounds, such as
15 and
16, when formed by intracellular cyclization following transport of a suitable precursor molecule, such as
14, may be selective prolonged inhibitors of cytosolic carbonic anhydrase due to intracellular entrapment. |
| doi_str_mv | 10.1016/j.bmc.2005.10.054 |
| format | Article |
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e]-1,2-thiazine-6-sulfonamide 1,1-dioxides, which have a quaternary ammonium moiety incorporated into their structures, were synthesized. All of the quaternary ammonium salts prepared in the present study are potent inhibitors of both human carbonic anhydrase-II and recombinant human carbonic anhydrase-IV; they are significantly more potent as inhibitors of these carbonic anhydrase isozymes than the previously reported inhibitor quaternary ammonium homosulfanilamide. By virtue of the permanent cationic charge on these compounds they are anticipated to be membrane-impermeable inhibitors of carbonic anhydrase. Spiro quaternary ammonium compounds, such as
15 and
16, when formed by intracellular cyclization following transport of a suitable precursor molecule, such as
14, may be selective prolonged inhibitors of cytosolic carbonic anhydrase due to intracellular entrapment.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2005.10.054</identifier><identifier>PMID: 16297631</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Biological and medical sciences ; Carbonic anhydrase ; Carbonic Anhydrase II - antagonists & inhibitors ; Carbonic Anhydrase II - genetics ; Carbonic Anhydrase Inhibitors - chemistry ; Carbonic Anhydrase Inhibitors - pharmacology ; Carbonic Anhydrase IV - antagonists & inhibitors ; Carbonic Anhydrase IV - genetics ; Cell Membrane - enzymology ; Cells, Cultured ; Enzyme inhibitor ; Humans ; Medical sciences ; Membrane-bound ; Miscellaneous ; Molecular Structure ; Oxides - chemistry ; Oxides - pharmacology ; Pharmacology. Drug treatments ; Quaternary ammonium ; Quaternary Ammonium Compounds - chemistry ; Quaternary Ammonium Compounds - pharmacology ; Sulfonamide ; Sulfonamides - chemistry ; Sulfonamides - pharmacology ; Thiazines - chemistry ; Thiazines - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry, 2006-03, Vol.14 (6), p.2052-2059</ispartof><rights>2005 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c412t-283cbffc432119261e864dc150d234f3a610f9902140257118855445f55565403</citedby><cites>FETCH-LOGICAL-c412t-283cbffc432119261e864dc150d234f3a610f9902140257118855445f55565403</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2005.10.054$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17586058$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16297631$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>May, Jesse A.</creatorcontrib><creatorcontrib>Namil, Abdelmoula</creatorcontrib><creatorcontrib>Chen, Hwang-Hsing</creatorcontrib><creatorcontrib>Dantanarayana, Anura P.</creatorcontrib><creatorcontrib>Dupré, Brian</creatorcontrib><creatorcontrib>Liao, John C.</creatorcontrib><title>Quaternary ammonium substituted thieno[3,2- e]-1,2-thiazine-6-sulfonamide 1,1-dioxides: Potential membrane-impermeable inhibitors of carbonic anhydrase</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Thieno[3,2-
e]-1,2-thiazine-6-sulfonamide 1,1-dioxides, which have a quaternary ammonium moiety incorporated into their structures, were synthesized. All of the quaternary ammonium salts prepared in the present study are potent inhibitors of both human carbonic anhydrase-II and recombinant human carbonic anhydrase-IV; they are significantly more potent as inhibitors of these carbonic anhydrase isozymes than the previously reported inhibitor quaternary ammonium homosulfanilamide. By virtue of the permanent cationic charge on these compounds they are anticipated to be membrane-impermeable inhibitors of carbonic anhydrase. Spiro quaternary ammonium compounds, such as
15 and
16, when formed by intracellular cyclization following transport of a suitable precursor molecule, such as
14, may be selective prolonged inhibitors of cytosolic carbonic anhydrase due to intracellular entrapment.</description><subject>Biological and medical sciences</subject><subject>Carbonic anhydrase</subject><subject>Carbonic Anhydrase II - antagonists & inhibitors</subject><subject>Carbonic Anhydrase II - genetics</subject><subject>Carbonic Anhydrase Inhibitors - chemistry</subject><subject>Carbonic Anhydrase Inhibitors - pharmacology</subject><subject>Carbonic Anhydrase IV - antagonists & inhibitors</subject><subject>Carbonic Anhydrase IV - genetics</subject><subject>Cell Membrane - enzymology</subject><subject>Cells, Cultured</subject><subject>Enzyme inhibitor</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Membrane-bound</subject><subject>Miscellaneous</subject><subject>Molecular Structure</subject><subject>Oxides - chemistry</subject><subject>Oxides - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Quaternary ammonium</subject><subject>Quaternary Ammonium Compounds - chemistry</subject><subject>Quaternary Ammonium Compounds - pharmacology</subject><subject>Sulfonamide</subject><subject>Sulfonamides - chemistry</subject><subject>Sulfonamides - pharmacology</subject><subject>Thiazines - chemistry</subject><subject>Thiazines - pharmacology</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUuLFDEQgBtR3HX1B3iRXPS0Paby6o57ksUXLKigJ5GQTlczGTqdMUmL6x_x75phBvamp0qKrx7U1zRPgW6Agnq52wzBbRilsv43VIp7zTkIJVrONdxvzqlWfUt7rc6aRznvKKVMaHjYnIFiulMczps_n1dbMC023RIbQlz8Gkheh1x8WQuOpGw9LvEbv2Qtwe8t1FhT9rdfsFVtXucpLjb4EQlcQjv6-Ku-8yvyKRZcirczCRiGZCvuwx5TQDvMSPyy9YMvMWUSJ-JsGupoR-yyvR2Tzfi4eTDZOeOTU7xovr598-X6fXvz8d2H69c3rRPASst67oZpcoIzAM0UYK_E6EDSkXExcauATlpTBoIy2QH0vZRCyElKqaSg_KJ5cey7T_HHirmY4LPDea4LxzUb1Smhqez-C4LWnVZcVxCOoEsx54ST2Scf6n0NUHPQZnamajMHbYdU1VZrnp2ar0PA8a7i5KkCz0-Azc7OU72n8_mO62SvqOwrd3XksN7sp8dksqv-HI4-oStmjP4fa_wFrfa0ug</recordid><startdate>20060315</startdate><enddate>20060315</enddate><creator>May, Jesse A.</creator><creator>Namil, Abdelmoula</creator><creator>Chen, Hwang-Hsing</creator><creator>Dantanarayana, Anura P.</creator><creator>Dupré, Brian</creator><creator>Liao, John C.</creator><general>Elsevier Ltd</general><general>Elsevier Science</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20060315</creationdate><title>Quaternary ammonium substituted thieno[3,2- e]-1,2-thiazine-6-sulfonamide 1,1-dioxides: Potential membrane-impermeable inhibitors of carbonic anhydrase</title><author>May, Jesse A. ; Namil, Abdelmoula ; Chen, Hwang-Hsing ; Dantanarayana, Anura P. ; Dupré, Brian ; Liao, John C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c412t-283cbffc432119261e864dc150d234f3a610f9902140257118855445f55565403</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Biological and medical sciences</topic><topic>Carbonic anhydrase</topic><topic>Carbonic Anhydrase II - antagonists & inhibitors</topic><topic>Carbonic Anhydrase II - genetics</topic><topic>Carbonic Anhydrase Inhibitors - chemistry</topic><topic>Carbonic Anhydrase Inhibitors - pharmacology</topic><topic>Carbonic Anhydrase IV - antagonists & inhibitors</topic><topic>Carbonic Anhydrase IV - genetics</topic><topic>Cell Membrane - enzymology</topic><topic>Cells, Cultured</topic><topic>Enzyme inhibitor</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Membrane-bound</topic><topic>Miscellaneous</topic><topic>Molecular Structure</topic><topic>Oxides - chemistry</topic><topic>Oxides - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Quaternary ammonium</topic><topic>Quaternary Ammonium Compounds - chemistry</topic><topic>Quaternary Ammonium Compounds - pharmacology</topic><topic>Sulfonamide</topic><topic>Sulfonamides - chemistry</topic><topic>Sulfonamides - pharmacology</topic><topic>Thiazines - chemistry</topic><topic>Thiazines - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>May, Jesse A.</creatorcontrib><creatorcontrib>Namil, Abdelmoula</creatorcontrib><creatorcontrib>Chen, Hwang-Hsing</creatorcontrib><creatorcontrib>Dantanarayana, Anura P.</creatorcontrib><creatorcontrib>Dupré, Brian</creatorcontrib><creatorcontrib>Liao, John C.</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>May, Jesse A.</au><au>Namil, Abdelmoula</au><au>Chen, Hwang-Hsing</au><au>Dantanarayana, Anura P.</au><au>Dupré, Brian</au><au>Liao, John C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Quaternary ammonium substituted thieno[3,2- e]-1,2-thiazine-6-sulfonamide 1,1-dioxides: Potential membrane-impermeable inhibitors of carbonic anhydrase</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2006-03-15</date><risdate>2006</risdate><volume>14</volume><issue>6</issue><spage>2052</spage><epage>2059</epage><pages>2052-2059</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Thieno[3,2-
e]-1,2-thiazine-6-sulfonamide 1,1-dioxides, which have a quaternary ammonium moiety incorporated into their structures, were synthesized. All of the quaternary ammonium salts prepared in the present study are potent inhibitors of both human carbonic anhydrase-II and recombinant human carbonic anhydrase-IV; they are significantly more potent as inhibitors of these carbonic anhydrase isozymes than the previously reported inhibitor quaternary ammonium homosulfanilamide. By virtue of the permanent cationic charge on these compounds they are anticipated to be membrane-impermeable inhibitors of carbonic anhydrase. Spiro quaternary ammonium compounds, such as
15 and
16, when formed by intracellular cyclization following transport of a suitable precursor molecule, such as
14, may be selective prolonged inhibitors of cytosolic carbonic anhydrase due to intracellular entrapment.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16297631</pmid><doi>10.1016/j.bmc.2005.10.054</doi><tpages>8</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2006-03, Vol.14 (6), p.2052-2059 |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Biological and medical sciences Carbonic anhydrase Carbonic Anhydrase II - antagonists & inhibitors Carbonic Anhydrase II - genetics Carbonic Anhydrase Inhibitors - chemistry Carbonic Anhydrase Inhibitors - pharmacology Carbonic Anhydrase IV - antagonists & inhibitors Carbonic Anhydrase IV - genetics Cell Membrane - enzymology Cells, Cultured Enzyme inhibitor Humans Medical sciences Membrane-bound Miscellaneous Molecular Structure Oxides - chemistry Oxides - pharmacology Pharmacology. Drug treatments Quaternary ammonium Quaternary Ammonium Compounds - chemistry Quaternary Ammonium Compounds - pharmacology Sulfonamide Sulfonamides - chemistry Sulfonamides - pharmacology Thiazines - chemistry Thiazines - pharmacology |
| title | Quaternary ammonium substituted thieno[3,2- e]-1,2-thiazine-6-sulfonamide 1,1-dioxides: Potential membrane-impermeable inhibitors of carbonic anhydrase |
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