Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides
[Display omitted] A group of homochiral quaternary ammonium sulfonamides bearing hydrophobic camphor derived moieties were synthesized and characterized. The described synthetic procedure is quick and efficient. The novel quaternary ammonium bromides were tested as antimicrobial and antifungal agent...
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| Veröffentlicht in: | European journal of pharmaceutical sciences 2014-12, Vol.65, p.29-37 |
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| container_title | European journal of pharmaceutical sciences |
| container_volume | 65 |
| creator | Mikláš, R. Miklášová, N. Bukovský, M. Horváth, B. Kubincová, J. Devínsky, F. |
| description | [Display omitted]
A group of homochiral quaternary ammonium sulfonamides bearing hydrophobic camphor derived moieties were synthesized and characterized. The described synthetic procedure is quick and efficient. The novel quaternary ammonium bromides were tested as antimicrobial and antifungal agents. They exhibited strong antimicrobial and also antifungal activity, especially N-{2-[((1S, 4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methylsulfonamido] ethyl}-N,N-dimethyltetradecan-1-aminium bromide 1c. The surface properties of prepared compounds were evaluated by surface tension measurements and critical micelle concentration (CMC) with surface tension at CMC (γCMC) was calculated. |
| doi_str_mv | 10.1016/j.ejps.2014.08.013 |
| format | Article |
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A group of homochiral quaternary ammonium sulfonamides bearing hydrophobic camphor derived moieties were synthesized and characterized. The described synthetic procedure is quick and efficient. The novel quaternary ammonium bromides were tested as antimicrobial and antifungal agents. They exhibited strong antimicrobial and also antifungal activity, especially N-{2-[((1S, 4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methylsulfonamido] ethyl}-N,N-dimethyltetradecan-1-aminium bromide 1c. The surface properties of prepared compounds were evaluated by surface tension measurements and critical micelle concentration (CMC) with surface tension at CMC (γCMC) was calculated.</description><identifier>ISSN: 0928-0987</identifier><identifier>EISSN: 1879-0720</identifier><identifier>DOI: 10.1016/j.ejps.2014.08.013</identifier><identifier>PMID: 25218991</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - pharmacology ; Antifungal Agents - chemical synthesis ; Antifungal Agents - pharmacology ; Antimicrobial activity ; Bromides - chemical synthesis ; Bromides - pharmacology ; Camphor - chemical synthesis ; Camphor - pharmacology ; Critical micelle concentration ; Homochiral camphorsulfonamides ; Hydrophobic and Hydrophilic Interactions ; Micelles ; Quaternary Ammonium Compounds - chemical synthesis ; Quaternary Ammonium Compounds - pharmacology ; Quaternary ammonium salts ; Structure-Activity Relationship ; Sulfonamides - chemical synthesis ; Sulfonamides - pharmacology ; Surface Properties ; Surface Tension</subject><ispartof>European journal of pharmaceutical sciences, 2014-12, Vol.65, p.29-37</ispartof><rights>2014 Elsevier B.V.</rights><rights>Copyright © 2014 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-e5035d778469ed21652e2e913fd08e71ce2bddab31ab692114f6a33e0dfa0ede3</citedby><cites>FETCH-LOGICAL-c356t-e5035d778469ed21652e2e913fd08e71ce2bddab31ab692114f6a33e0dfa0ede3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejps.2014.08.013$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25218991$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mikláš, R.</creatorcontrib><creatorcontrib>Miklášová, N.</creatorcontrib><creatorcontrib>Bukovský, M.</creatorcontrib><creatorcontrib>Horváth, B.</creatorcontrib><creatorcontrib>Kubincová, J.</creatorcontrib><creatorcontrib>Devínsky, F.</creatorcontrib><title>Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides</title><title>European journal of pharmaceutical sciences</title><addtitle>Eur J Pharm Sci</addtitle><description>[Display omitted]
A group of homochiral quaternary ammonium sulfonamides bearing hydrophobic camphor derived moieties were synthesized and characterized. The described synthetic procedure is quick and efficient. The novel quaternary ammonium bromides were tested as antimicrobial and antifungal agents. They exhibited strong antimicrobial and also antifungal activity, especially N-{2-[((1S, 4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methylsulfonamido] ethyl}-N,N-dimethyltetradecan-1-aminium bromide 1c. The surface properties of prepared compounds were evaluated by surface tension measurements and critical micelle concentration (CMC) with surface tension at CMC (γCMC) was calculated.</description><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antimicrobial activity</subject><subject>Bromides - chemical synthesis</subject><subject>Bromides - pharmacology</subject><subject>Camphor - chemical synthesis</subject><subject>Camphor - pharmacology</subject><subject>Critical micelle concentration</subject><subject>Homochiral camphorsulfonamides</subject><subject>Hydrophobic and Hydrophilic Interactions</subject><subject>Micelles</subject><subject>Quaternary Ammonium Compounds - chemical synthesis</subject><subject>Quaternary Ammonium Compounds - pharmacology</subject><subject>Quaternary ammonium salts</subject><subject>Structure-Activity Relationship</subject><subject>Sulfonamides - chemical synthesis</subject><subject>Sulfonamides - pharmacology</subject><subject>Surface Properties</subject><subject>Surface Tension</subject><issn>0928-0987</issn><issn>1879-0720</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kD1P5DAURa0VaBnY_QNboJQUm_BsTxJbokFo-ZCQKGBry7FfNB7iONgJEv8ejwYoKazXnHvlewj5Q6GiQJvzbYXbKVUM6LoCUQHlP8iKilaW0DI4ICuQTJQgRXtEjlPaAkAjWvhJjljNqJCSrsjz49s4bzC59LdIS-y1wUKPNr_ZeWdi6JweiimGCePsMBWhL1LwWLwsesY46vhWaO_D6BZfbIIPZuNiThjtp02IuXPow6i9s5h-kcNeDwl_f9wT8v_639PVbXn_cHN3dXlfGl43c4k18Nq2rVg3Ei2jTc2QoaS8tyCwpQZZZ63uONVdIxml677RnCPYXgNa5CfkbN-bv_2yYJqVd8ngMOgRw5IUbZiUdS04yyjbo3lpShF7NUXn8yhFQe0kq63aSVY7yQqEypJz6PSjf-k82q_Ip9UMXOwBzCtfHUaVjMPRoHURzaxscN_1vwP7_JD1</recordid><startdate>20141218</startdate><enddate>20141218</enddate><creator>Mikláš, R.</creator><creator>Miklášová, N.</creator><creator>Bukovský, M.</creator><creator>Horváth, B.</creator><creator>Kubincová, J.</creator><creator>Devínsky, F.</creator><general>Elsevier B.V</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>20141218</creationdate><title>Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides</title><author>Mikláš, R. ; Miklášová, N. ; Bukovský, M. ; Horváth, B. ; Kubincová, J. ; Devínsky, F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-e5035d778469ed21652e2e913fd08e71ce2bddab31ab692114f6a33e0dfa0ede3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Anti-Infective Agents - chemical synthesis</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antimicrobial activity</topic><topic>Bromides - chemical synthesis</topic><topic>Bromides - pharmacology</topic><topic>Camphor - chemical synthesis</topic><topic>Camphor - pharmacology</topic><topic>Critical micelle concentration</topic><topic>Homochiral camphorsulfonamides</topic><topic>Hydrophobic and Hydrophilic Interactions</topic><topic>Micelles</topic><topic>Quaternary Ammonium Compounds - chemical synthesis</topic><topic>Quaternary Ammonium Compounds - pharmacology</topic><topic>Quaternary ammonium salts</topic><topic>Structure-Activity Relationship</topic><topic>Sulfonamides - chemical synthesis</topic><topic>Sulfonamides - pharmacology</topic><topic>Surface Properties</topic><topic>Surface Tension</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mikláš, R.</creatorcontrib><creatorcontrib>Miklášová, N.</creatorcontrib><creatorcontrib>Bukovský, M.</creatorcontrib><creatorcontrib>Horváth, B.</creatorcontrib><creatorcontrib>Kubincová, J.</creatorcontrib><creatorcontrib>Devínsky, F.</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>European journal of pharmaceutical sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mikláš, R.</au><au>Miklášová, N.</au><au>Bukovský, M.</au><au>Horváth, B.</au><au>Kubincová, J.</au><au>Devínsky, F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides</atitle><jtitle>European journal of pharmaceutical sciences</jtitle><addtitle>Eur J Pharm Sci</addtitle><date>2014-12-18</date><risdate>2014</risdate><volume>65</volume><spage>29</spage><epage>37</epage><pages>29-37</pages><issn>0928-0987</issn><eissn>1879-0720</eissn><abstract>[Display omitted]
A group of homochiral quaternary ammonium sulfonamides bearing hydrophobic camphor derived moieties were synthesized and characterized. The described synthetic procedure is quick and efficient. The novel quaternary ammonium bromides were tested as antimicrobial and antifungal agents. They exhibited strong antimicrobial and also antifungal activity, especially N-{2-[((1S, 4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methylsulfonamido] ethyl}-N,N-dimethyltetradecan-1-aminium bromide 1c. The surface properties of prepared compounds were evaluated by surface tension measurements and critical micelle concentration (CMC) with surface tension at CMC (γCMC) was calculated.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>25218991</pmid><doi>10.1016/j.ejps.2014.08.013</doi><tpages>9</tpages></addata></record> |
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| ispartof | European journal of pharmaceutical sciences, 2014-12, Vol.65, p.29-37 |
| issn | 0928-0987 1879-0720 |
| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Anti-Infective Agents - chemical synthesis Anti-Infective Agents - pharmacology Antifungal Agents - chemical synthesis Antifungal Agents - pharmacology Antimicrobial activity Bromides - chemical synthesis Bromides - pharmacology Camphor - chemical synthesis Camphor - pharmacology Critical micelle concentration Homochiral camphorsulfonamides Hydrophobic and Hydrophilic Interactions Micelles Quaternary Ammonium Compounds - chemical synthesis Quaternary Ammonium Compounds - pharmacology Quaternary ammonium salts Structure-Activity Relationship Sulfonamides - chemical synthesis Sulfonamides - pharmacology Surface Properties Surface Tension |
| title | Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides |
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