Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and 5-chloro-2-hydroxybenzoic acid scaffold
A series of novel sulfonamides containing 5-chloro-2-hydroxybenzaldehyde or 5-chloro-2-hydroxybenzoic acid scaffolds were designed, synthesized and characterized by IR, 1H NMR and 13C NMR. All ten target synthesized derivatives and starting sulfonamides were evaluated in vitro for the activity again...
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| Veröffentlicht in: | European journal of medicinal chemistry 2012-04, Vol.50, p.433-440 |
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| container_title | European journal of medicinal chemistry |
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| creator | Krátký, Martin Vinšová, Jarmila Volková, Marie Buchta, Vladimír Trejtnar, František Stolaříková, Jiřina |
| description | A series of novel sulfonamides containing 5-chloro-2-hydroxybenzaldehyde or 5-chloro-2-hydroxybenzoic acid scaffolds were designed, synthesized and characterized by IR, 1H NMR and 13C NMR. All ten target synthesized derivatives and starting sulfonamides were evaluated in vitro for the activity against Gram-positive and Gram-negative bacteria, fungi, Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium kansasii. The most active compound against methicillin-sensitive and methicillin-resistant Staphyloccoccus aureus was 5-chloro-N-{4-[N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl]phenyl}-2-hydroxybenzamide with MIC 15.62–31.25 μmol/L. 4-Amino-N-(thiazol-2-yl)benzenesulfonamide and 4-(5-chloro-2-hydroxybenzylideneamino)-N-(thiazol-2-yl)benzenesulfonamide have shown the best activity against M. kansasii at the concentrations of 1–4 μmol/L. The efficacy against other strains was weaker and the studied derivatives exhibited almost none antifungal potency.
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► New sulfonamide Schiff bases and amides with salicylic moiety were synthesized. ► In vitro activity against Gram-positive bacteria, MIC ≥15.62 μmol/L. ► Activity against methicillin-resistant Staphylococcus aureus. ► Activity against mycobacteria, especially against Mycobacterium kansasii with MIC ≥1 μmol/L. |
| doi_str_mv | 10.1016/j.ejmech.2012.01.060 |
| format | Article |
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[Display omitted]
► New sulfonamide Schiff bases and amides with salicylic moiety were synthesized. ► In vitro activity against Gram-positive bacteria, MIC ≥15.62 μmol/L. ► Activity against methicillin-resistant Staphylococcus aureus. ► Activity against mycobacteria, especially against Mycobacterium kansasii with MIC ≥1 μmol/L.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2012.01.060</identifier><identifier>PMID: 22365879</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - pharmacology ; Antibacterial activity ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antimycobacterial activity ; Bacteria - drug effects ; Benzamides - chemical synthesis ; Benzamides - pharmacology ; Biological and medical sciences ; Fungi - drug effects ; In vitro activity ; Magnetic Resonance Spectroscopy ; Medical sciences ; Microbial Sensitivity Tests ; Molecular Structure ; Pharmacology. Drug treatments ; Salicylanilide ; Schiff base ; Spectrophotometry, Infrared ; Structure-Activity Relationship ; Sulfonamide ; Sulfonamides - chemical synthesis ; Sulfonamides - chemistry ; Sulfonamides - pharmacology ; Thiazoles - chemical synthesis ; Thiazoles - pharmacology</subject><ispartof>European journal of medicinal chemistry, 2012-04, Vol.50, p.433-440</ispartof><rights>2012 Elsevier Masson SAS</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c457t-cebe3d9813d59ca87f80e42eb022024be755baa6afe9826e7c61ee95779761a33</citedby><cites>FETCH-LOGICAL-c457t-cebe3d9813d59ca87f80e42eb022024be755baa6afe9826e7c61ee95779761a33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0223523412000761$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27902,27903,65308</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25755371$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22365879$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Krátký, Martin</creatorcontrib><creatorcontrib>Vinšová, Jarmila</creatorcontrib><creatorcontrib>Volková, Marie</creatorcontrib><creatorcontrib>Buchta, Vladimír</creatorcontrib><creatorcontrib>Trejtnar, František</creatorcontrib><creatorcontrib>Stolaříková, Jiřina</creatorcontrib><title>Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and 5-chloro-2-hydroxybenzoic acid scaffold</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>A series of novel sulfonamides containing 5-chloro-2-hydroxybenzaldehyde or 5-chloro-2-hydroxybenzoic acid scaffolds were designed, synthesized and characterized by IR, 1H NMR and 13C NMR. All ten target synthesized derivatives and starting sulfonamides were evaluated in vitro for the activity against Gram-positive and Gram-negative bacteria, fungi, Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium kansasii. The most active compound against methicillin-sensitive and methicillin-resistant Staphyloccoccus aureus was 5-chloro-N-{4-[N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl]phenyl}-2-hydroxybenzamide with MIC 15.62–31.25 μmol/L. 4-Amino-N-(thiazol-2-yl)benzenesulfonamide and 4-(5-chloro-2-hydroxybenzylideneamino)-N-(thiazol-2-yl)benzenesulfonamide have shown the best activity against M. kansasii at the concentrations of 1–4 μmol/L. The efficacy against other strains was weaker and the studied derivatives exhibited almost none antifungal potency.
[Display omitted]
► New sulfonamide Schiff bases and amides with salicylic moiety were synthesized. ► In vitro activity against Gram-positive bacteria, MIC ≥15.62 μmol/L. ► Activity against methicillin-resistant Staphylococcus aureus. ► Activity against mycobacteria, especially against Mycobacterium kansasii with MIC ≥1 μmol/L.</description><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>Antibacterial activity</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antimycobacterial activity</subject><subject>Bacteria - drug effects</subject><subject>Benzamides - chemical synthesis</subject><subject>Benzamides - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Fungi - drug effects</subject><subject>In vitro activity</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Salicylanilide</subject><subject>Schiff base</subject><subject>Spectrophotometry, Infrared</subject><subject>Structure-Activity Relationship</subject><subject>Sulfonamide</subject><subject>Sulfonamides - chemical synthesis</subject><subject>Sulfonamides - chemistry</subject><subject>Sulfonamides - pharmacology</subject><subject>Thiazoles - chemical synthesis</subject><subject>Thiazoles - pharmacology</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE9rHCEYh6W0NNsk36CUuZScZqrOqOMlEELTFgK5JGdx9LXr4miqs6Fb8uFj2G17Sk7yyvP--T0IfSS4I5jwL5sONjOYdUcxoR0mHeb4DVoRwce2p2x4i1aY0r5ltB-O0IdSNhhjxjF-j47qP2ejkCv0eBEXP3uT0-R1aLRZ_INfdk1yTdkGl6KevYXSmBQX7aOPPxvWmnVIObW0Xe9sTr93E8Q_OlioJTQ62heQ5E1d4G1TjHYuBXuC3jkdCpwe3mN0d_X19vJ7e33z7cflxXVrBiaW1sAEvZUj6S2TRo_CjRgGClPNh-kwgWBs0pprB3KkHIThBEAyIaTgRPf9MTrbz73P6dcWyqJmXwyEoCOkbVGSSkIkH2klhz1ZhZSSwan77Gedd4pg9axdbdReu3rWrjBRVXtt-3RYsJ1msP-a_nquwOcDoGv44LKOxpf_HKsRekEqd77noOp48JBVMR6iAeszmEXZ5F-_5AnhNqS2</recordid><startdate>20120401</startdate><enddate>20120401</enddate><creator>Krátký, Martin</creator><creator>Vinšová, Jarmila</creator><creator>Volková, Marie</creator><creator>Buchta, Vladimír</creator><creator>Trejtnar, František</creator><creator>Stolaříková, Jiřina</creator><general>Elsevier Masson SAS</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>20120401</creationdate><title>Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and 5-chloro-2-hydroxybenzoic acid scaffold</title><author>Krátký, Martin ; Vinšová, Jarmila ; Volková, Marie ; Buchta, Vladimír ; Trejtnar, František ; Stolaříková, Jiřina</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c457t-cebe3d9813d59ca87f80e42eb022024be755baa6afe9826e7c61ee95779761a33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Anti-Infective Agents - chemical synthesis</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>Antibacterial activity</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antimycobacterial activity</topic><topic>Bacteria - drug effects</topic><topic>Benzamides - chemical synthesis</topic><topic>Benzamides - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Fungi - drug effects</topic><topic>In vitro activity</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Salicylanilide</topic><topic>Schiff base</topic><topic>Spectrophotometry, Infrared</topic><topic>Structure-Activity Relationship</topic><topic>Sulfonamide</topic><topic>Sulfonamides - chemical synthesis</topic><topic>Sulfonamides - chemistry</topic><topic>Sulfonamides - pharmacology</topic><topic>Thiazoles - chemical synthesis</topic><topic>Thiazoles - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Krátký, Martin</creatorcontrib><creatorcontrib>Vinšová, Jarmila</creatorcontrib><creatorcontrib>Volková, Marie</creatorcontrib><creatorcontrib>Buchta, Vladimír</creatorcontrib><creatorcontrib>Trejtnar, František</creatorcontrib><creatorcontrib>Stolaříková, Jiřina</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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Krátký, Martin</au><au>Vinšová, Jarmila</au><au>Volková, Marie</au><au>Buchta, Vladimír</au><au>Trejtnar, František</au><au>Stolaříková, Jiřina</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and 5-chloro-2-hydroxybenzoic acid scaffold</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2012-04-01</date><risdate>2012</risdate><volume>50</volume><spage>433</spage><epage>440</epage><pages>433-440</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>A series of novel sulfonamides containing 5-chloro-2-hydroxybenzaldehyde or 5-chloro-2-hydroxybenzoic acid scaffolds were designed, synthesized and characterized by IR, 1H NMR and 13C NMR. All ten target synthesized derivatives and starting sulfonamides were evaluated in vitro for the activity against Gram-positive and Gram-negative bacteria, fungi, Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium kansasii. The most active compound against methicillin-sensitive and methicillin-resistant Staphyloccoccus aureus was 5-chloro-N-{4-[N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl]phenyl}-2-hydroxybenzamide with MIC 15.62–31.25 μmol/L. 4-Amino-N-(thiazol-2-yl)benzenesulfonamide and 4-(5-chloro-2-hydroxybenzylideneamino)-N-(thiazol-2-yl)benzenesulfonamide have shown the best activity against M. kansasii at the concentrations of 1–4 μmol/L. The efficacy against other strains was weaker and the studied derivatives exhibited almost none antifungal potency.
[Display omitted]
► New sulfonamide Schiff bases and amides with salicylic moiety were synthesized. ► In vitro activity against Gram-positive bacteria, MIC ≥15.62 μmol/L. ► Activity against methicillin-resistant Staphylococcus aureus. ► Activity against mycobacteria, especially against Mycobacterium kansasii with MIC ≥1 μmol/L.</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>22365879</pmid><doi>10.1016/j.ejmech.2012.01.060</doi><tpages>8</tpages></addata></record> |
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| ispartof | European journal of medicinal chemistry, 2012-04, Vol.50, p.433-440 |
| issn | 0223-5234 1768-3254 |
| language | eng |
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| subjects | Anti-Infective Agents - chemical synthesis Anti-Infective Agents - pharmacology Antibacterial activity Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Antimycobacterial activity Bacteria - drug effects Benzamides - chemical synthesis Benzamides - pharmacology Biological and medical sciences Fungi - drug effects In vitro activity Magnetic Resonance Spectroscopy Medical sciences Microbial Sensitivity Tests Molecular Structure Pharmacology. Drug treatments Salicylanilide Schiff base Spectrophotometry, Infrared Structure-Activity Relationship Sulfonamide Sulfonamides - chemical synthesis Sulfonamides - chemistry Sulfonamides - pharmacology Thiazoles - chemical synthesis Thiazoles - pharmacology |
| title | Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and 5-chloro-2-hydroxybenzoic acid scaffold |
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