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...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Archiv der Pharmazie (Weinheim) 2014-10, Vol.347 (10), p.748-755
Hauptverfasser: Ouahrouch, Abdelaaziz, Ighachane, Hana, Taourirte, Moha, Engels, Joachim W., Sedra, My Hassan, Lazrek, Hassan B.
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 755
container_issue 10
container_start_page 748
container_title Archiv der Pharmazie (Weinheim)
container_volume 347
creator Ouahrouch, Abdelaaziz
Ighachane, Hana
Taourirte, Moha
Engels, Joachim W.
Sedra, My Hassan
Lazrek, Hassan B.
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
format Article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4225497</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3447982631</sourcerecordid><originalsourceid>FETCH-LOGICAL-c6462-64c13c0696a6cd18abcdd797eef368e276a7b41cd88e986bee076e72ccb2fbda3</originalsourceid><addsrcrecordid>eNqFkc1v1DAQxS0EokvhyhFF4sKh2fojsRMOSEtbWtRSYCniaDn2pHXrOIvtLGz_erJsWRUuHEaekX_vaUYPoecETwnGdF8Fs5hSTAo8Fn2AJqSkJC9IVTxEE8x4mXPK2A56EuM1xphhWj5GO7TEVUUqPEHdW_C3trNG3fYOcrJH91iegv09ZierJliTfRh7PTiIr7MvK5-uINqYKW-yo6Vyg0q291nbh2zmk22UTjDq3f56agd_qVw208kubVo9RY9a5SI8u3t30dd3RxcHJ_nZx-P3B7OzXPOC05wXmjCNec0V14ZUqtHGiFoAtIxXQAVXoimINlUFdcUbACw4CKp1Q9vGKLaL3mx8F0PTgdHgU1BOLoLtVFjJXln594-3V_KyX8qC0rKoxWjw6s4g9N8HiEl2NmpwTnnohyhJyQUuiRDFiL78B73uh-DH89YU54SWjI3UdEPp0McYoN0uQ7BcJynXScptkqPgxf0Ttvif6Eag3gA_rIPVf-zkbH746b55vtHamODnVqvCjeSCiVJ-Oz-Wn-fnhxen-FTO2S9zG7w7</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1566612533</pqid></control><display><type>article</type><title>Benzimidazole-1,2,3-triazole Hybrid Molecules: Synthesis and Evaluation for Antibacterial/Antifungal Activity</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Ouahrouch, Abdelaaziz ; Ighachane, Hana ; Taourirte, Moha ; Engels, Joachim W. ; Sedra, My Hassan ; Lazrek, Hassan B.</creator><creatorcontrib>Ouahrouch, Abdelaaziz ; Ighachane, Hana ; Taourirte, Moha ; Engels, Joachim W. ; Sedra, My Hassan ; Lazrek, Hassan B.</creatorcontrib><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><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 &amp; development ; Gram-Negative Bacteria - drug effects ; Gram-Negative Bacteria - growth &amp; development ; Gram-Positive Bacteria - drug effects ; Gram-Positive Bacteria - growth &amp; development ; Hybrid molecules ; Microbial Sensitivity Tests ; Molecular Structure ; Structure-Activity Relationship ; Triazoles - chemical synthesis ; Triazoles - pharmacology ; Verticillium - drug effects ; Verticillium - growth &amp; 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 &amp; Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH &amp; Co. KGaA, Weinheim.</rights><rights>2014 The Authors. Archiv der Pharmazie Published by WILEY-VCH Verlag GmbH &amp; 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 &amp; development</subject><subject>Gram-Negative Bacteria - drug effects</subject><subject>Gram-Negative Bacteria - growth &amp; development</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>Gram-Positive Bacteria - growth &amp; 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 &amp; 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 &amp; development</topic><topic>Gram-Negative Bacteria - drug effects</topic><topic>Gram-Negative Bacteria - growth &amp; development</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>Gram-Positive Bacteria - growth &amp; 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 &amp; 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 &amp; 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>
fulltext fulltext
identifier ISSN: 0365-6233
ispartof Archiv der Pharmazie (Weinheim), 2014-10, Vol.347 (10), p.748-755
issn 0365-6233
1521-4184
language eng
recordid cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4225497
source MEDLINE; Wiley Online Library Journals Frontfile Complete
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
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-29T17%3A09%3A06IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Benzimidazole-1,2,3-triazole%20Hybrid%20Molecules:%20Synthesis%20and%20Evaluation%20for%20Antibacterial/Antifungal%20Activity&rft.jtitle=Archiv%20der%20Pharmazie%20(Weinheim)&rft.au=Ouahrouch,%20Abdelaaziz&rft.date=2014-10&rft.volume=347&rft.issue=10&rft.spage=748&rft.epage=755&rft.pages=748-755&rft.issn=0365-6233&rft.eissn=1521-4184&rft_id=info:doi/10.1002/ardp.201400142&rft_dat=%3Cproquest_pubme%3E3447982631%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1566612533&rft_id=info:pmid/25088180&rfr_iscdi=true