Benzimidazole-1,2,3-triazole Hybrid Molecules: Synthesis and Evaluation for Antibacterial/Antifungal Activity
A novel series of hybrid molecules 4a–i and 5a–i were prepared by condensation of 4‐(trimethylsilylethynyl)benzaldehyde 1 with substituted o‐phenylenediamines. These in turn were reacted with 2‐(azidomethoxy)ethyl acetate in a Cu alkyne–azide cycloaddition (CuAAC) to generate the 1,2,3‐triazole phar...
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Veröffentlicht in: | Archiv der Pharmazie (Weinheim) 2014-10, Vol.347 (10), p.748-755 |
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description | A novel series of hybrid molecules 4a–i and 5a–i were prepared by condensation of 4‐(trimethylsilylethynyl)benzaldehyde 1 with substituted o‐phenylenediamines. These in turn were reacted with 2‐(azidomethoxy)ethyl acetate in a Cu alkyne–azide cycloaddition (CuAAC) to generate the 1,2,3‐triazole pharmacophore under microwave assistance. The newly synthesized compounds were examined for their in vitro antimicrobial activities against Gram‐positive and Gram‐negative bacteria and the phytopathogenic fungi Verticillium dahliae and Fusarium oxysporum f. sp. albedinis. 2‐((4‐(4‐(5‐Trifluoromethyl benzimidazol‐2‐yl)phenyl)‐1,2,3‐triazol‐1‐yl)methoxy)ethanol 5e showed a moderate inhibition of 30% in the Foa sporulation test.
Hybrid molecules including benzimidazole, benzene, and triazole rings were synthesized and characterized. The compounds were assessed for their in vitro antimicrobial activities against Gram‐positive and Gram‐negative bacteria and phytopathogenic fungi. 2‐((4‐(4‐(5‐Trifluoromethyl benzimidazol‐2‐yl)phenyl)‐1,2,3‐triazol‐1‐yl)‐methoxy)ethanol 5e was found to achieve moderate inhibition of 30% in the Foa sporulation test. |
doi_str_mv | 10.1002/ardp.201400142 |
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Hybrid molecules including benzimidazole, benzene, and triazole rings were synthesized and characterized. The compounds were assessed for their in vitro antimicrobial activities against Gram‐positive and Gram‐negative bacteria and phytopathogenic fungi. 2‐((4‐(4‐(5‐Trifluoromethyl benzimidazol‐2‐yl)phenyl)‐1,2,3‐triazol‐1‐yl)‐methoxy)ethanol 5e was found to achieve moderate inhibition of 30% in the Foa sporulation test.</description><identifier>ISSN: 0365-6233</identifier><identifier>EISSN: 1521-4184</identifier><identifier>DOI: 10.1002/ardp.201400142</identifier><identifier>PMID: 25088180</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - pharmacology ; Antibacterial activity ; Antifungal activity ; Antifungal Agents - chemical synthesis ; Antifungal Agents - pharmacology ; Bacteriology ; Benzimidazoles - chemical synthesis ; Benzimidazoles - pharmacology ; Drug Design ; Fusarium - drug effects ; Fusarium - growth & development ; Gram-Negative Bacteria - drug effects ; Gram-Negative Bacteria - growth & development ; Gram-Positive Bacteria - drug effects ; Gram-Positive Bacteria - growth & development ; Hybrid molecules ; Microbial Sensitivity Tests ; Molecular Structure ; Structure-Activity Relationship ; Triazoles - chemical synthesis ; Triazoles - pharmacology ; Verticillium - drug effects ; Verticillium - growth & development</subject><ispartof>Archiv der Pharmazie (Weinheim), 2014-10, Vol.347 (10), p.748-755</ispartof><rights>2014 The Authors. Archiv der Pharmazie Published by WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 The Authors. Archiv der Pharmazie Published by WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 2014</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6462-64c13c0696a6cd18abcdd797eef368e276a7b41cd88e986bee076e72ccb2fbda3</citedby><cites>FETCH-LOGICAL-c6462-64c13c0696a6cd18abcdd797eef368e276a7b41cd88e986bee076e72ccb2fbda3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fardp.201400142$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fardp.201400142$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25088180$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ouahrouch, Abdelaaziz</creatorcontrib><creatorcontrib>Ighachane, Hana</creatorcontrib><creatorcontrib>Taourirte, Moha</creatorcontrib><creatorcontrib>Engels, Joachim W.</creatorcontrib><creatorcontrib>Sedra, My Hassan</creatorcontrib><creatorcontrib>Lazrek, Hassan B.</creatorcontrib><title>Benzimidazole-1,2,3-triazole Hybrid Molecules: Synthesis and Evaluation for Antibacterial/Antifungal Activity</title><title>Archiv der Pharmazie (Weinheim)</title><addtitle>Arch. Pharm. Chem. Life Sci</addtitle><description>A novel series of hybrid molecules 4a–i and 5a–i were prepared by condensation of 4‐(trimethylsilylethynyl)benzaldehyde 1 with substituted o‐phenylenediamines. These in turn were reacted with 2‐(azidomethoxy)ethyl acetate in a Cu alkyne–azide cycloaddition (CuAAC) to generate the 1,2,3‐triazole pharmacophore under microwave assistance. The newly synthesized compounds were examined for their in vitro antimicrobial activities against Gram‐positive and Gram‐negative bacteria and the phytopathogenic fungi Verticillium dahliae and Fusarium oxysporum f. sp. albedinis. 2‐((4‐(4‐(5‐Trifluoromethyl benzimidazol‐2‐yl)phenyl)‐1,2,3‐triazol‐1‐yl)methoxy)ethanol 5e showed a moderate inhibition of 30% in the Foa sporulation test.
Hybrid molecules including benzimidazole, benzene, and triazole rings were synthesized and characterized. The compounds were assessed for their in vitro antimicrobial activities against Gram‐positive and Gram‐negative bacteria and phytopathogenic fungi. 2‐((4‐(4‐(5‐Trifluoromethyl benzimidazol‐2‐yl)phenyl)‐1,2,3‐triazol‐1‐yl)‐methoxy)ethanol 5e was found to achieve moderate inhibition of 30% in the Foa sporulation test.</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial activity</subject><subject>Antifungal activity</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - pharmacology</subject><subject>Bacteriology</subject><subject>Benzimidazoles - chemical synthesis</subject><subject>Benzimidazoles - pharmacology</subject><subject>Drug Design</subject><subject>Fusarium - drug effects</subject><subject>Fusarium - growth & development</subject><subject>Gram-Negative Bacteria - drug effects</subject><subject>Gram-Negative Bacteria - growth & development</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>Gram-Positive Bacteria - growth & development</subject><subject>Hybrid molecules</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Structure-Activity Relationship</subject><subject>Triazoles - chemical synthesis</subject><subject>Triazoles - pharmacology</subject><subject>Verticillium - drug effects</subject><subject>Verticillium - growth & development</subject><issn>0365-6233</issn><issn>1521-4184</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>EIF</sourceid><recordid>eNqFkc1v1DAQxS0EokvhyhFF4sKh2fojsRMOSEtbWtRSYCniaDn2pHXrOIvtLGz_erJsWRUuHEaekX_vaUYPoecETwnGdF8Fs5hSTAo8Fn2AJqSkJC9IVTxEE8x4mXPK2A56EuM1xphhWj5GO7TEVUUqPEHdW_C3trNG3fYOcrJH91iegv09ZierJliTfRh7PTiIr7MvK5-uINqYKW-yo6Vyg0q291nbh2zmk22UTjDq3f56agd_qVw208kubVo9RY9a5SI8u3t30dd3RxcHJ_nZx-P3B7OzXPOC05wXmjCNec0V14ZUqtHGiFoAtIxXQAVXoimINlUFdcUbACw4CKp1Q9vGKLaL3mx8F0PTgdHgU1BOLoLtVFjJXln594-3V_KyX8qC0rKoxWjw6s4g9N8HiEl2NmpwTnnohyhJyQUuiRDFiL78B73uh-DH89YU54SWjI3UdEPp0McYoN0uQ7BcJynXScptkqPgxf0Ttvif6Eag3gA_rIPVf-zkbH746b55vtHamODnVqvCjeSCiVJ-Oz-Wn-fnhxen-FTO2S9zG7w7</recordid><startdate>201410</startdate><enddate>201410</enddate><creator>Ouahrouch, Abdelaaziz</creator><creator>Ighachane, Hana</creator><creator>Taourirte, Moha</creator><creator>Engels, Joachim W.</creator><creator>Sedra, My Hassan</creator><creator>Lazrek, Hassan B.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>24P</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>K9.</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>201410</creationdate><title>Benzimidazole-1,2,3-triazole Hybrid Molecules: Synthesis and Evaluation for Antibacterial/Antifungal Activity</title><author>Ouahrouch, Abdelaaziz ; Ighachane, Hana ; Taourirte, Moha ; Engels, Joachim W. ; Sedra, My Hassan ; Lazrek, Hassan B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6462-64c13c0696a6cd18abcdd797eef368e276a7b41cd88e986bee076e72ccb2fbda3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial activity</topic><topic>Antifungal activity</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - pharmacology</topic><topic>Bacteriology</topic><topic>Benzimidazoles - chemical synthesis</topic><topic>Benzimidazoles - pharmacology</topic><topic>Drug Design</topic><topic>Fusarium - drug effects</topic><topic>Fusarium - growth & development</topic><topic>Gram-Negative Bacteria - drug effects</topic><topic>Gram-Negative Bacteria - growth & development</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>Gram-Positive Bacteria - growth & development</topic><topic>Hybrid molecules</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Structure-Activity Relationship</topic><topic>Triazoles - chemical synthesis</topic><topic>Triazoles - pharmacology</topic><topic>Verticillium - drug effects</topic><topic>Verticillium - growth & development</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ouahrouch, Abdelaaziz</creatorcontrib><creatorcontrib>Ighachane, Hana</creatorcontrib><creatorcontrib>Taourirte, Moha</creatorcontrib><creatorcontrib>Engels, Joachim W.</creatorcontrib><creatorcontrib>Sedra, My Hassan</creatorcontrib><creatorcontrib>Lazrek, Hassan B.</creatorcontrib><collection>Istex</collection><collection>Wiley Online Library Open Access</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Archiv der Pharmazie (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ouahrouch, Abdelaaziz</au><au>Ighachane, Hana</au><au>Taourirte, Moha</au><au>Engels, Joachim W.</au><au>Sedra, My Hassan</au><au>Lazrek, Hassan B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Benzimidazole-1,2,3-triazole Hybrid Molecules: Synthesis and Evaluation for Antibacterial/Antifungal Activity</atitle><jtitle>Archiv der Pharmazie (Weinheim)</jtitle><addtitle>Arch. Pharm. Chem. Life Sci</addtitle><date>2014-10</date><risdate>2014</risdate><volume>347</volume><issue>10</issue><spage>748</spage><epage>755</epage><pages>748-755</pages><issn>0365-6233</issn><eissn>1521-4184</eissn><abstract>A novel series of hybrid molecules 4a–i and 5a–i were prepared by condensation of 4‐(trimethylsilylethynyl)benzaldehyde 1 with substituted o‐phenylenediamines. These in turn were reacted with 2‐(azidomethoxy)ethyl acetate in a Cu alkyne–azide cycloaddition (CuAAC) to generate the 1,2,3‐triazole pharmacophore under microwave assistance. The newly synthesized compounds were examined for their in vitro antimicrobial activities against Gram‐positive and Gram‐negative bacteria and the phytopathogenic fungi Verticillium dahliae and Fusarium oxysporum f. sp. albedinis. 2‐((4‐(4‐(5‐Trifluoromethyl benzimidazol‐2‐yl)phenyl)‐1,2,3‐triazol‐1‐yl)methoxy)ethanol 5e showed a moderate inhibition of 30% in the Foa sporulation test.
Hybrid molecules including benzimidazole, benzene, and triazole rings were synthesized and characterized. The compounds were assessed for their in vitro antimicrobial activities against Gram‐positive and Gram‐negative bacteria and phytopathogenic fungi. 2‐((4‐(4‐(5‐Trifluoromethyl benzimidazol‐2‐yl)phenyl)‐1,2,3‐triazol‐1‐yl)‐methoxy)ethanol 5e was found to achieve moderate inhibition of 30% in the Foa sporulation test.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>25088180</pmid><doi>10.1002/ardp.201400142</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - pharmacology Antibacterial activity Antifungal activity Antifungal Agents - chemical synthesis Antifungal Agents - pharmacology Bacteriology Benzimidazoles - chemical synthesis Benzimidazoles - pharmacology Drug Design Fusarium - drug effects Fusarium - growth & development Gram-Negative Bacteria - drug effects Gram-Negative Bacteria - growth & development Gram-Positive Bacteria - drug effects Gram-Positive Bacteria - growth & development Hybrid molecules Microbial Sensitivity Tests Molecular Structure Structure-Activity Relationship Triazoles - chemical synthesis Triazoles - pharmacology Verticillium - drug effects Verticillium - growth & development |
title | Benzimidazole-1,2,3-triazole Hybrid Molecules: Synthesis and Evaluation for Antibacterial/Antifungal Activity |
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