Synthesis and antimicrobial studies of hydrazone derivatives of 4-[3-(2,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid and 4-[3-(3,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid
[Display omitted] •Benign synthesis of new pyrazole derivatives.•29 novel molecules.•MIC as low as 0.78 μM (S. aureus, MRSA, B. subtilis, and A. baumannii).•Non-toxic to mammalian cells.•Potential LpxM inhibitors. Microbial resistance to antibiotics is an unresolved global concern, which needs urgen...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2018-09, Vol.28 (17), p.2914-2919 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Zakeyah, A.A. Whitt, J. Duke, C. Gilmore, D.F. Meeker, D.G. Smeltzer, M.S. Alam, M.A. |
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•Benign synthesis of new pyrazole derivatives.•29 novel molecules.•MIC as low as 0.78 μM (S. aureus, MRSA, B. subtilis, and A. baumannii).•Non-toxic to mammalian cells.•Potential LpxM inhibitors.
Microbial resistance to antibiotics is an unresolved global concern, which needs urgent and coordinated action. One of the guidelines of the Centers for Disease Control and Preventions (CDC) to combat antibiotic resistance is the development of new antibiotics to treat drug-resistant bacteria. In our effort to find new antibiotics, we report the synthesis and antimicrobial studies of 30 new pyrazole derivatives. These novel molecules have been synthesized by using readily available starting materials and benign reaction conditions. Some of these molecules have shown activity with MIC values as low as 0.78 µg/mL against four bacterial strains; Staphylococcus aureus, methicillin-resistant S. aureus, Bacillus subtilis, and Acinetobacter baumannii. Furthermore, active molecules are non-toxic to mammalian cell line.▪ |
| doi_str_mv | 10.1016/j.bmcl.2018.07.016 |
| format | Article |
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•Benign synthesis of new pyrazole derivatives.•29 novel molecules.•MIC as low as 0.78 μM (S. aureus, MRSA, B. subtilis, and A. baumannii).•Non-toxic to mammalian cells.•Potential LpxM inhibitors.
Microbial resistance to antibiotics is an unresolved global concern, which needs urgent and coordinated action. One of the guidelines of the Centers for Disease Control and Preventions (CDC) to combat antibiotic resistance is the development of new antibiotics to treat drug-resistant bacteria. In our effort to find new antibiotics, we report the synthesis and antimicrobial studies of 30 new pyrazole derivatives. These novel molecules have been synthesized by using readily available starting materials and benign reaction conditions. Some of these molecules have shown activity with MIC values as low as 0.78 µg/mL against four bacterial strains; Staphylococcus aureus, methicillin-resistant S. aureus, Bacillus subtilis, and Acinetobacter baumannii. Furthermore, active molecules are non-toxic to mammalian cell line.▪</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2018.07.016</identifier><identifier>PMID: 30017319</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Acinetobacter baumannii ; Acinetobacter baumannii - drug effects ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antimicrobial ; Bacillus subtilis - drug effects ; Benzoates - chemical synthesis ; Benzoates - chemistry ; Benzoates - pharmacology ; Dose-Response Relationship, Drug ; Hydrazone ; Hydrazones - chemical synthesis ; Hydrazones - chemistry ; Hydrazones - pharmacology ; Microbial Sensitivity Tests ; Molecular Structure ; MRSA ; Pyrazole ; Staphylococcus aureus - drug effects ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2018-09, Vol.28 (17), p.2914-2919</ispartof><rights>2018</rights><rights>Published by Elsevier Ltd.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c455t-c3cf2491f08b022cb83857ab48dc76ac8e9f2ffd54de57aa466577cc84b58bc73</citedby><cites>FETCH-LOGICAL-c455t-c3cf2491f08b022cb83857ab48dc76ac8e9f2ffd54de57aa466577cc84b58bc73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2018.07.016$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,777,781,882,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30017319$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zakeyah, A.A.</creatorcontrib><creatorcontrib>Whitt, J.</creatorcontrib><creatorcontrib>Duke, C.</creatorcontrib><creatorcontrib>Gilmore, D.F.</creatorcontrib><creatorcontrib>Meeker, D.G.</creatorcontrib><creatorcontrib>Smeltzer, M.S.</creatorcontrib><creatorcontrib>Alam, M.A.</creatorcontrib><title>Synthesis and antimicrobial studies of hydrazone derivatives of 4-[3-(2,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid and 4-[3-(3,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
•Benign synthesis of new pyrazole derivatives.•29 novel molecules.•MIC as low as 0.78 μM (S. aureus, MRSA, B. subtilis, and A. baumannii).•Non-toxic to mammalian cells.•Potential LpxM inhibitors.
Microbial resistance to antibiotics is an unresolved global concern, which needs urgent and coordinated action. One of the guidelines of the Centers for Disease Control and Preventions (CDC) to combat antibiotic resistance is the development of new antibiotics to treat drug-resistant bacteria. In our effort to find new antibiotics, we report the synthesis and antimicrobial studies of 30 new pyrazole derivatives. These novel molecules have been synthesized by using readily available starting materials and benign reaction conditions. Some of these molecules have shown activity with MIC values as low as 0.78 µg/mL against four bacterial strains; Staphylococcus aureus, methicillin-resistant S. aureus, Bacillus subtilis, and Acinetobacter baumannii. Furthermore, active molecules are non-toxic to mammalian cell line.▪</description><subject>Acinetobacter baumannii</subject><subject>Acinetobacter baumannii - drug effects</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antimicrobial</subject><subject>Bacillus subtilis - drug effects</subject><subject>Benzoates - chemical synthesis</subject><subject>Benzoates - chemistry</subject><subject>Benzoates - pharmacology</subject><subject>Dose-Response Relationship, Drug</subject><subject>Hydrazone</subject><subject>Hydrazones - chemical synthesis</subject><subject>Hydrazones - chemistry</subject><subject>Hydrazones - pharmacology</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>MRSA</subject><subject>Pyrazole</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqdkd-K1DAUxoMo7rj6Al5ILxVMTZq0SUEWZFFXWPBCBUEk5M-Jk6FthqQz0H09X8yM1UVvvPAi5PCd8_0OyYfQY0pqSmj3Yleb0Q51Q6isiaiLdAdtKO84Zpy0d9GG9B3Bsuefz9CDnHeEUE44v4_OWCkFo_0Gff-wTPMWcsiVnlw5cxiDTdEEPVR5PrgAuYq-2i4u6Zs4QeUghaOew3FtcPyF4afNc45d8MMhprjfwrQMzzDHPqZxGTC9wvvl5C4lXoavBqabGGylbXA_t64M9r-Mh-ie10OGR7_uc_TpzeuPl1f4-v3bd5evrrHlbTtjy6xveE89kYY0jTWSyVZow6WzotNWQu8b713LHRRd865rhbBWctNKYwU7Rxcrd38wIzgL05z0oPYpjDotKuqg_u5MYau-xaPqKBOk4QXQrIDywTkn8LdeStQpUrVTp0jVKVJFhCpSMT35c-ut5XeGZeDlOgDl7ccASWUbYLLgQgI7KxfDv_g_AB1mtnA</recordid><startdate>20180915</startdate><enddate>20180915</enddate><creator>Zakeyah, A.A.</creator><creator>Whitt, J.</creator><creator>Duke, C.</creator><creator>Gilmore, D.F.</creator><creator>Meeker, D.G.</creator><creator>Smeltzer, M.S.</creator><creator>Alam, M.A.</creator><general>Elsevier Ltd</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>5PM</scope></search><sort><creationdate>20180915</creationdate><title>Synthesis and antimicrobial studies of hydrazone derivatives of 4-[3-(2,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid and 4-[3-(3,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid</title><author>Zakeyah, A.A. ; Whitt, J. ; Duke, C. ; Gilmore, D.F. ; Meeker, D.G. ; Smeltzer, M.S. ; Alam, M.A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c455t-c3cf2491f08b022cb83857ab48dc76ac8e9f2ffd54de57aa466577cc84b58bc73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acinetobacter baumannii</topic><topic>Acinetobacter baumannii - drug effects</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antimicrobial</topic><topic>Bacillus subtilis - drug effects</topic><topic>Benzoates - chemical synthesis</topic><topic>Benzoates - chemistry</topic><topic>Benzoates - pharmacology</topic><topic>Dose-Response Relationship, Drug</topic><topic>Hydrazone</topic><topic>Hydrazones - chemical synthesis</topic><topic>Hydrazones - chemistry</topic><topic>Hydrazones - pharmacology</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>MRSA</topic><topic>Pyrazole</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zakeyah, A.A.</creatorcontrib><creatorcontrib>Whitt, J.</creatorcontrib><creatorcontrib>Duke, C.</creatorcontrib><creatorcontrib>Gilmore, D.F.</creatorcontrib><creatorcontrib>Meeker, D.G.</creatorcontrib><creatorcontrib>Smeltzer, M.S.</creatorcontrib><creatorcontrib>Alam, M.A.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zakeyah, A.A.</au><au>Whitt, J.</au><au>Duke, C.</au><au>Gilmore, D.F.</au><au>Meeker, D.G.</au><au>Smeltzer, M.S.</au><au>Alam, M.A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antimicrobial studies of hydrazone derivatives of 4-[3-(2,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid and 4-[3-(3,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2018-09-15</date><risdate>2018</risdate><volume>28</volume><issue>17</issue><spage>2914</spage><epage>2919</epage><pages>2914-2919</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
•Benign synthesis of new pyrazole derivatives.•29 novel molecules.•MIC as low as 0.78 μM (S. aureus, MRSA, B. subtilis, and A. baumannii).•Non-toxic to mammalian cells.•Potential LpxM inhibitors.
Microbial resistance to antibiotics is an unresolved global concern, which needs urgent and coordinated action. One of the guidelines of the Centers for Disease Control and Preventions (CDC) to combat antibiotic resistance is the development of new antibiotics to treat drug-resistant bacteria. In our effort to find new antibiotics, we report the synthesis and antimicrobial studies of 30 new pyrazole derivatives. These novel molecules have been synthesized by using readily available starting materials and benign reaction conditions. Some of these molecules have shown activity with MIC values as low as 0.78 µg/mL against four bacterial strains; Staphylococcus aureus, methicillin-resistant S. aureus, Bacillus subtilis, and Acinetobacter baumannii. Furthermore, active molecules are non-toxic to mammalian cell line.▪</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>30017319</pmid><doi>10.1016/j.bmcl.2018.07.016</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Acinetobacter baumannii Acinetobacter baumannii - drug effects Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antimicrobial Bacillus subtilis - drug effects Benzoates - chemical synthesis Benzoates - chemistry Benzoates - pharmacology Dose-Response Relationship, Drug Hydrazone Hydrazones - chemical synthesis Hydrazones - chemistry Hydrazones - pharmacology Microbial Sensitivity Tests Molecular Structure MRSA Pyrazole Staphylococcus aureus - drug effects Structure-Activity Relationship |
| title | Synthesis and antimicrobial studies of hydrazone derivatives of 4-[3-(2,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid and 4-[3-(3,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid |
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