Microwave assisted, one-pot synthesis of 5-nitro- 2-aryl substituted-1H-benzimidazole libraries: Screening in vitro for antimicrobial activity
The efficient and rapid synthesis of 5-nitro-2-aryl substituted-1H-benzimidazole libraries (1a-1j) has been established. Thus, both microwave and conventional cyclo-condensation of 4-nitro ortho-phenylenediamine with various phenoxyacetic acids were carried out in the presence of HCl catalyst. The m...
Gespeichert in:
| Veröffentlicht in: | Journal of enzyme inhibition and medicinal chemistry 2009-10, Vol.24 (5), p.1095-1100 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1100 |
|---|---|
| container_issue | 5 |
| container_start_page | 1095 |
| container_title | Journal of enzyme inhibition and medicinal chemistry |
| container_volume | 24 |
| creator | Hosamani, Kallappa Mahadevappa Seetharamareddy, Harisha Reddy Keri, Rangappa Sangappa Hanamanthagouda, Manohar Shirugumbi Moloney, Mark G. |
| description | The efficient and rapid synthesis of 5-nitro-2-aryl substituted-1H-benzimidazole libraries (1a-1j) has been established. Thus, both microwave and conventional cyclo-condensation of 4-nitro ortho-phenylenediamine with various phenoxyacetic acids were carried out in the presence of HCl catalyst. The microwave synthesis route afforded advantages, such as good to excellent yields, shorter reaction time (2.5-3.5 min), readily available starting material, and simple purification procedure, which distinguish the present protocol from other existing methods used for the synthesis of benzimidazole libraries. Bioassay indicated that all the compounds showed in vitro antimicrobial activity against Vancomycin resistant enteroccoccus, Staphylococcus aureus, Micrococcus, Bacillus subtilis (gram-positive bacteria) and Shigella dysentery, Escherichia coli (gram-negative bacteria) and Candida albicans, Aspergillus niger, Penicillium (fungi). The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards. |
| doi_str_mv | 10.1080/14756360802632716 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_infor</sourceid><recordid>TN_cdi_informahealthcare_journals_10_1080_14756360802632716</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>734055849</sourcerecordid><originalsourceid>FETCH-LOGICAL-c405t-7415165ca93e4e6ebc1998def98fccfc22cce1b46caa8c4223c551e917c9bc483</originalsourceid><addsrcrecordid>eNp9kcFu1DAQhi0EoqXwAFyQb1wwxI7jJMAFVUCRijgA52gymbCuHHuxnVbbh-CZ8WpXIITUk0fj7_9n9A9jT2X1UlZd9UrqtjG1KaUytWqlucdO9z1h6lbf_1Mbc8IepXRVVUoqqR-yE9m3rdKdPmW_PluM4QauiUNKNmWaXvDgSWxD5mnn84ZKl4eZN8LbHIPgSkDcOZ7WMWWb16IQ8kKM5G_tYie4DY64s2OEaCm95l8xEnnrf3Dr-fXegs8hcvC54GX2aMFxwGzL3-4xezCDS_Tk-J6x7x_efzu_EJdfPn46f3cpUFdNFq2WjTQNQl-TJkMjyr7vJpr7bkacUSlEkqM2CNChVqrGppHUyxb7EXVXn7HnB99tDD9XSnlYbEJyDjyFNQ1tXeY0ne4LKQ9kWTWlSPOwjXYpCQyyGvZXGP67QtE8O7qv40LTX8Ux9gK8PQDWlywWuAnRTUOGnQtxjuDRpqG-y__NP_INgcsbhEjDVVijL8ndsd1vFGGq0A</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>734055849</pqid></control><display><type>article</type><title>Microwave assisted, one-pot synthesis of 5-nitro- 2-aryl substituted-1H-benzimidazole libraries: Screening in vitro for antimicrobial activity</title><source>MEDLINE</source><source>Taylor & Francis</source><source>EZB-FREE-00999 freely available EZB journals</source><creator>Hosamani, Kallappa Mahadevappa ; Seetharamareddy, Harisha Reddy ; Keri, Rangappa Sangappa ; Hanamanthagouda, Manohar Shirugumbi ; Moloney, Mark G.</creator><creatorcontrib>Hosamani, Kallappa Mahadevappa ; Seetharamareddy, Harisha Reddy ; Keri, Rangappa Sangappa ; Hanamanthagouda, Manohar Shirugumbi ; Moloney, Mark G.</creatorcontrib><description>The efficient and rapid synthesis of 5-nitro-2-aryl substituted-1H-benzimidazole libraries (1a-1j) has been established. Thus, both microwave and conventional cyclo-condensation of 4-nitro ortho-phenylenediamine with various phenoxyacetic acids were carried out in the presence of HCl catalyst. The microwave synthesis route afforded advantages, such as good to excellent yields, shorter reaction time (2.5-3.5 min), readily available starting material, and simple purification procedure, which distinguish the present protocol from other existing methods used for the synthesis of benzimidazole libraries. Bioassay indicated that all the compounds showed in vitro antimicrobial activity against Vancomycin resistant enteroccoccus, Staphylococcus aureus, Micrococcus, Bacillus subtilis (gram-positive bacteria) and Shigella dysentery, Escherichia coli (gram-negative bacteria) and Candida albicans, Aspergillus niger, Penicillium (fungi). The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards.</description><identifier>ISSN: 1475-6366</identifier><identifier>EISSN: 1475-6374</identifier><identifier>DOI: 10.1080/14756360802632716</identifier><identifier>PMID: 19772484</identifier><language>eng</language><publisher>England: Informa UK Ltd</publisher><subject>Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - pharmacology ; antimicrobial activity ; Bacteria - drug effects ; Benzimidazole libraries ; Benzimidazoles - chemical synthesis ; Benzimidazoles - chemistry ; Benzimidazoles - pharmacology ; Catalysis ; Fungi - drug effects ; Microbial Sensitivity Tests ; microwave irradiation ; Microwaves ; Molecular Structure ; one-pot synthesis ; Penicillium - drug effects ; Staphylococcus - drug effects</subject><ispartof>Journal of enzyme inhibition and medicinal chemistry, 2009-10, Vol.24 (5), p.1095-1100</ispartof><rights>2009 Informa UK Ltd 2009</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c405t-7415165ca93e4e6ebc1998def98fccfc22cce1b46caa8c4223c551e917c9bc483</citedby><cites>FETCH-LOGICAL-c405t-7415165ca93e4e6ebc1998def98fccfc22cce1b46caa8c4223c551e917c9bc483</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/14756360802632716$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/14756360802632716$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>314,777,781,27905,27906,59626,60415,61200,61381</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19772484$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hosamani, Kallappa Mahadevappa</creatorcontrib><creatorcontrib>Seetharamareddy, Harisha Reddy</creatorcontrib><creatorcontrib>Keri, Rangappa Sangappa</creatorcontrib><creatorcontrib>Hanamanthagouda, Manohar Shirugumbi</creatorcontrib><creatorcontrib>Moloney, Mark G.</creatorcontrib><title>Microwave assisted, one-pot synthesis of 5-nitro- 2-aryl substituted-1H-benzimidazole libraries: Screening in vitro for antimicrobial activity</title><title>Journal of enzyme inhibition and medicinal chemistry</title><addtitle>J Enzyme Inhib Med Chem</addtitle><description>The efficient and rapid synthesis of 5-nitro-2-aryl substituted-1H-benzimidazole libraries (1a-1j) has been established. Thus, both microwave and conventional cyclo-condensation of 4-nitro ortho-phenylenediamine with various phenoxyacetic acids were carried out in the presence of HCl catalyst. The microwave synthesis route afforded advantages, such as good to excellent yields, shorter reaction time (2.5-3.5 min), readily available starting material, and simple purification procedure, which distinguish the present protocol from other existing methods used for the synthesis of benzimidazole libraries. Bioassay indicated that all the compounds showed in vitro antimicrobial activity against Vancomycin resistant enteroccoccus, Staphylococcus aureus, Micrococcus, Bacillus subtilis (gram-positive bacteria) and Shigella dysentery, Escherichia coli (gram-negative bacteria) and Candida albicans, Aspergillus niger, Penicillium (fungi). The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards.</description><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>antimicrobial activity</subject><subject>Bacteria - drug effects</subject><subject>Benzimidazole libraries</subject><subject>Benzimidazoles - chemical synthesis</subject><subject>Benzimidazoles - chemistry</subject><subject>Benzimidazoles - pharmacology</subject><subject>Catalysis</subject><subject>Fungi - drug effects</subject><subject>Microbial Sensitivity Tests</subject><subject>microwave irradiation</subject><subject>Microwaves</subject><subject>Molecular Structure</subject><subject>one-pot synthesis</subject><subject>Penicillium - drug effects</subject><subject>Staphylococcus - drug effects</subject><issn>1475-6366</issn><issn>1475-6374</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kcFu1DAQhi0EoqXwAFyQb1wwxI7jJMAFVUCRijgA52gymbCuHHuxnVbbh-CZ8WpXIITUk0fj7_9n9A9jT2X1UlZd9UrqtjG1KaUytWqlucdO9z1h6lbf_1Mbc8IepXRVVUoqqR-yE9m3rdKdPmW_PluM4QauiUNKNmWaXvDgSWxD5mnn84ZKl4eZN8LbHIPgSkDcOZ7WMWWb16IQ8kKM5G_tYie4DY64s2OEaCm95l8xEnnrf3Dr-fXegs8hcvC54GX2aMFxwGzL3-4xezCDS_Tk-J6x7x_efzu_EJdfPn46f3cpUFdNFq2WjTQNQl-TJkMjyr7vJpr7bkacUSlEkqM2CNChVqrGppHUyxb7EXVXn7HnB99tDD9XSnlYbEJyDjyFNQ1tXeY0ne4LKQ9kWTWlSPOwjXYpCQyyGvZXGP67QtE8O7qv40LTX8Ux9gK8PQDWlywWuAnRTUOGnQtxjuDRpqG-y__NP_INgcsbhEjDVVijL8ndsd1vFGGq0A</recordid><startdate>200910</startdate><enddate>200910</enddate><creator>Hosamani, Kallappa Mahadevappa</creator><creator>Seetharamareddy, Harisha Reddy</creator><creator>Keri, Rangappa Sangappa</creator><creator>Hanamanthagouda, Manohar Shirugumbi</creator><creator>Moloney, Mark G.</creator><general>Informa UK Ltd</general><general>Taylor & Francis</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>200910</creationdate><title>Microwave assisted, one-pot synthesis of 5-nitro- 2-aryl substituted-1H-benzimidazole libraries: Screening in vitro for antimicrobial activity</title><author>Hosamani, Kallappa Mahadevappa ; Seetharamareddy, Harisha Reddy ; Keri, Rangappa Sangappa ; Hanamanthagouda, Manohar Shirugumbi ; Moloney, Mark G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c405t-7415165ca93e4e6ebc1998def98fccfc22cce1b46caa8c4223c551e917c9bc483</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Anti-Infective Agents - chemical synthesis</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>antimicrobial activity</topic><topic>Bacteria - drug effects</topic><topic>Benzimidazole libraries</topic><topic>Benzimidazoles - chemical synthesis</topic><topic>Benzimidazoles - chemistry</topic><topic>Benzimidazoles - pharmacology</topic><topic>Catalysis</topic><topic>Fungi - drug effects</topic><topic>Microbial Sensitivity Tests</topic><topic>microwave irradiation</topic><topic>Microwaves</topic><topic>Molecular Structure</topic><topic>one-pot synthesis</topic><topic>Penicillium - drug effects</topic><topic>Staphylococcus - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hosamani, Kallappa Mahadevappa</creatorcontrib><creatorcontrib>Seetharamareddy, Harisha Reddy</creatorcontrib><creatorcontrib>Keri, Rangappa Sangappa</creatorcontrib><creatorcontrib>Hanamanthagouda, Manohar Shirugumbi</creatorcontrib><creatorcontrib>Moloney, Mark G.</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>Journal of enzyme inhibition and medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hosamani, Kallappa Mahadevappa</au><au>Seetharamareddy, Harisha Reddy</au><au>Keri, Rangappa Sangappa</au><au>Hanamanthagouda, Manohar Shirugumbi</au><au>Moloney, Mark G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave assisted, one-pot synthesis of 5-nitro- 2-aryl substituted-1H-benzimidazole libraries: Screening in vitro for antimicrobial activity</atitle><jtitle>Journal of enzyme inhibition and medicinal chemistry</jtitle><addtitle>J Enzyme Inhib Med Chem</addtitle><date>2009-10</date><risdate>2009</risdate><volume>24</volume><issue>5</issue><spage>1095</spage><epage>1100</epage><pages>1095-1100</pages><issn>1475-6366</issn><eissn>1475-6374</eissn><abstract>The efficient and rapid synthesis of 5-nitro-2-aryl substituted-1H-benzimidazole libraries (1a-1j) has been established. Thus, both microwave and conventional cyclo-condensation of 4-nitro ortho-phenylenediamine with various phenoxyacetic acids were carried out in the presence of HCl catalyst. The microwave synthesis route afforded advantages, such as good to excellent yields, shorter reaction time (2.5-3.5 min), readily available starting material, and simple purification procedure, which distinguish the present protocol from other existing methods used for the synthesis of benzimidazole libraries. Bioassay indicated that all the compounds showed in vitro antimicrobial activity against Vancomycin resistant enteroccoccus, Staphylococcus aureus, Micrococcus, Bacillus subtilis (gram-positive bacteria) and Shigella dysentery, Escherichia coli (gram-negative bacteria) and Candida albicans, Aspergillus niger, Penicillium (fungi). The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards.</abstract><cop>England</cop><pub>Informa UK Ltd</pub><pmid>19772484</pmid><doi>10.1080/14756360802632716</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1475-6366 |
| ispartof | Journal of enzyme inhibition and medicinal chemistry, 2009-10, Vol.24 (5), p.1095-1100 |
| issn | 1475-6366 1475-6374 |
| language | eng |
| recordid | cdi_informahealthcare_journals_10_1080_14756360802632716 |
| source | MEDLINE; Taylor & Francis; EZB-FREE-00999 freely available EZB journals |
| subjects | Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology antimicrobial activity Bacteria - drug effects Benzimidazole libraries Benzimidazoles - chemical synthesis Benzimidazoles - chemistry Benzimidazoles - pharmacology Catalysis Fungi - drug effects Microbial Sensitivity Tests microwave irradiation Microwaves Molecular Structure one-pot synthesis Penicillium - drug effects Staphylococcus - drug effects |
| title | Microwave assisted, one-pot synthesis of 5-nitro- 2-aryl substituted-1H-benzimidazole libraries: Screening in vitro for antimicrobial activity |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-18T00%3A15%3A54IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_infor&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Microwave%20assisted,%20one-pot%20synthesis%20of%205-nitro-%202-aryl%20substituted-1H-benzimidazole%20libraries:%20Screening%20in%20vitro%20for%20antimicrobial%20activity&rft.jtitle=Journal%20of%20enzyme%20inhibition%20and%20medicinal%20chemistry&rft.au=Hosamani,%20Kallappa%20Mahadevappa&rft.date=2009-10&rft.volume=24&rft.issue=5&rft.spage=1095&rft.epage=1100&rft.pages=1095-1100&rft.issn=1475-6366&rft.eissn=1475-6374&rft_id=info:doi/10.1080/14756360802632716&rft_dat=%3Cproquest_infor%3E734055849%3C/proquest_infor%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=734055849&rft_id=info:pmid/19772484&rfr_iscdi=true |