Design, synthesis, antimicrobial activity and molecular modeling studies of novel benzofuroxan derivatives against Staphylococcus aureus
A new series of 14 4-substituted [ N′-(benzofuroxan-5-yl)methylene] benzohydrazides with structure analogous of nifuroxazide were synthesized and tested against standard and multidrug-resistant Staphylococcus aureus strains. Molecular modification is a quite promising strategy in the design and deve...
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Veröffentlicht in: | Bioorganic & medicinal chemistry 2009-04, Vol.17 (8), p.3028-3036 |
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creator | Jorge, Salomão Dória Masunari, Andrea Rangel-Yagui, Carlota Oliveira Pasqualoto, Kerly Fernanda Mesquita Tavares, Leoberto Costa |
description | A new series of 14 4-substituted [
N′-(benzofuroxan-5-yl)methylene] benzohydrazides with structure analogous of nifuroxazide were synthesized and tested against standard and multidrug-resistant
Staphylococcus aureus strains.
Molecular modification is a quite promising strategy in the design and development of drug analogs with better bioavailability, higher intrinsic activity and less toxicity. In the search of new leads with potential antimicrobial activity, a new series of 14 4-substituted [
N′-(benzofuroxan-5-yl)methylene]benzohydrazides, nifuroxazide derivatives, were synthesized and tested against standard and multidrug-resistant
Staphylococcus aureus strains. The selection of the substituent groups was based on physicochemical properties, such as hydrophobicity and electronic effect. These properties were also evaluated through the lipophilic and electrostatic potential maps, respectively, considering the compounds with better biological profile. Twelve compounds exhibited similar bacteriostatic activity against standard and multidrug-resistant strains. The most active compound was the 4-CF
3 substituted derivative, which presented a minimum inhibitory concentration (MIC) value of 14.6–13.1
μg/mL, and a
Clog
P value of 1.87. The results highlight the benzofuroxan derivatives as potential leads for designing new future antimicrobial drug candidates. |
doi_str_mv | 10.1016/j.bmc.2009.03.011 |
format | Article |
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N′-(benzofuroxan-5-yl)methylene] benzohydrazides with structure analogous of nifuroxazide were synthesized and tested against standard and multidrug-resistant
Staphylococcus aureus strains.
Molecular modification is a quite promising strategy in the design and development of drug analogs with better bioavailability, higher intrinsic activity and less toxicity. In the search of new leads with potential antimicrobial activity, a new series of 14 4-substituted [
N′-(benzofuroxan-5-yl)methylene]benzohydrazides, nifuroxazide derivatives, were synthesized and tested against standard and multidrug-resistant
Staphylococcus aureus strains. The selection of the substituent groups was based on physicochemical properties, such as hydrophobicity and electronic effect. These properties were also evaluated through the lipophilic and electrostatic potential maps, respectively, considering the compounds with better biological profile. Twelve compounds exhibited similar bacteriostatic activity against standard and multidrug-resistant strains. The most active compound was the 4-CF
3 substituted derivative, which presented a minimum inhibitory concentration (MIC) value of 14.6–13.1
μg/mL, and a
Clog
P value of 1.87. The results highlight the benzofuroxan derivatives as potential leads for designing new future antimicrobial drug candidates.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2009.03.011</identifier><identifier>PMID: 19324556</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - pharmacology ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Benzofuroxan derivatives ; Benzoxazoles - chemical synthesis ; Benzoxazoles - chemistry ; Benzoxazoles - pharmacology ; Biological and medical sciences ; Drug Design ; Hydroxybenzoates - chemical synthesis ; Hydroxybenzoates - chemistry ; Hydroxybenzoates - pharmacology ; Medical sciences ; MIC ; Microbial Sensitivity Tests ; Models, Molecular ; Molecular modeling ; Molecular modification ; MRSA ; Nitrofurans - chemical synthesis ; Nitrofurans - chemistry ; Nitrofurans - pharmacology ; Pharmacology. Drug treatments ; Staphylococcus aureus ; Staphylococcus aureus - drug effects ; Structure-Activity Relationship ; VISA</subject><ispartof>Bioorganic & medicinal chemistry, 2009-04, Vol.17 (8), p.3028-3036</ispartof><rights>2009 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c522t-1843ab0979d27d03aa914c46663ff4f28017316dceed1c375a498b5ac851ef293</citedby><cites>FETCH-LOGICAL-c522t-1843ab0979d27d03aa914c46663ff4f28017316dceed1c375a498b5ac851ef293</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2009.03.011$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21391720$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19324556$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jorge, Salomão Dória</creatorcontrib><creatorcontrib>Masunari, Andrea</creatorcontrib><creatorcontrib>Rangel-Yagui, Carlota Oliveira</creatorcontrib><creatorcontrib>Pasqualoto, Kerly Fernanda Mesquita</creatorcontrib><creatorcontrib>Tavares, Leoberto Costa</creatorcontrib><title>Design, synthesis, antimicrobial activity and molecular modeling studies of novel benzofuroxan derivatives against Staphylococcus aureus</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A new series of 14 4-substituted [
N′-(benzofuroxan-5-yl)methylene] benzohydrazides with structure analogous of nifuroxazide were synthesized and tested against standard and multidrug-resistant
Staphylococcus aureus strains.
Molecular modification is a quite promising strategy in the design and development of drug analogs with better bioavailability, higher intrinsic activity and less toxicity. In the search of new leads with potential antimicrobial activity, a new series of 14 4-substituted [
N′-(benzofuroxan-5-yl)methylene]benzohydrazides, nifuroxazide derivatives, were synthesized and tested against standard and multidrug-resistant
Staphylococcus aureus strains. The selection of the substituent groups was based on physicochemical properties, such as hydrophobicity and electronic effect. These properties were also evaluated through the lipophilic and electrostatic potential maps, respectively, considering the compounds with better biological profile. Twelve compounds exhibited similar bacteriostatic activity against standard and multidrug-resistant strains. The most active compound was the 4-CF
3 substituted derivative, which presented a minimum inhibitory concentration (MIC) value of 14.6–13.1
μg/mL, and a
Clog
P value of 1.87. The results highlight the benzofuroxan derivatives as potential leads for designing new future antimicrobial drug candidates.</description><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Benzofuroxan derivatives</subject><subject>Benzoxazoles - chemical synthesis</subject><subject>Benzoxazoles - chemistry</subject><subject>Benzoxazoles - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Drug Design</subject><subject>Hydroxybenzoates - chemical synthesis</subject><subject>Hydroxybenzoates - chemistry</subject><subject>Hydroxybenzoates - pharmacology</subject><subject>Medical sciences</subject><subject>MIC</subject><subject>Microbial Sensitivity Tests</subject><subject>Models, Molecular</subject><subject>Molecular modeling</subject><subject>Molecular modification</subject><subject>MRSA</subject><subject>Nitrofurans - chemical synthesis</subject><subject>Nitrofurans - chemistry</subject><subject>Nitrofurans - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Staphylococcus aureus</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>VISA</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc9u1DAQhy0EotvCA3BBvsCpCf6TOLE4oUIBqRIH4Gw59mTrlWMvtrNieQIeG1e7ghunGY2--Wn0DUIvKGkpoeLNrp0W0zJCZEt4Syh9hDa0E13DuaSP0YZIMTZklOICXea8I4SwTtKn6IJKzrq-Fxv0-z1ktw3XOB9Dua99vsY6FLc4k-LktMfaFHdw5VjHFi_Rg1m9TrWz4F3Y4lxW6yDjOOMQD-DxBOFXnNcUf-qALSR30DWhEnqrXcgFfy16f3_00URj1jpeE6z5GXoya5_h-bleoe-3H77dfGruvnz8fPPurjE9Y6WhY8f1ROQgLRss4VpL2plOCMHnuZvZSOjAqbAGwFLDh153cpx6bcaewswkv0KvT7n7FH-skItaXDbgvQ4Q16wY6YnoOa0gPYFVRM4JZrVPbtHpqChRD_rVTlX96kG_IlxV_XXn5Tl8nRaw_zbOvivw6gzobLSfkw7G5b8co_VxAyOVe3vioKo4OEgqGwfBgHUJTFE2uv-c8QePBKXd</recordid><startdate>20090415</startdate><enddate>20090415</enddate><creator>Jorge, Salomão Dória</creator><creator>Masunari, Andrea</creator><creator>Rangel-Yagui, Carlota Oliveira</creator><creator>Pasqualoto, Kerly Fernanda Mesquita</creator><creator>Tavares, Leoberto Costa</creator><general>Elsevier Ltd</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>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20090415</creationdate><title>Design, synthesis, antimicrobial activity and molecular modeling studies of novel benzofuroxan derivatives against Staphylococcus aureus</title><author>Jorge, Salomão Dória ; Masunari, Andrea ; Rangel-Yagui, Carlota Oliveira ; Pasqualoto, Kerly Fernanda Mesquita ; Tavares, Leoberto Costa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c522t-1843ab0979d27d03aa914c46663ff4f28017316dceed1c375a498b5ac851ef293</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>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Benzofuroxan derivatives</topic><topic>Benzoxazoles - chemical synthesis</topic><topic>Benzoxazoles - chemistry</topic><topic>Benzoxazoles - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Drug Design</topic><topic>Hydroxybenzoates - chemical synthesis</topic><topic>Hydroxybenzoates - chemistry</topic><topic>Hydroxybenzoates - pharmacology</topic><topic>Medical sciences</topic><topic>MIC</topic><topic>Microbial Sensitivity Tests</topic><topic>Models, Molecular</topic><topic>Molecular modeling</topic><topic>Molecular modification</topic><topic>MRSA</topic><topic>Nitrofurans - chemical synthesis</topic><topic>Nitrofurans - chemistry</topic><topic>Nitrofurans - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Staphylococcus aureus</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>VISA</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jorge, Salomão Dória</creatorcontrib><creatorcontrib>Masunari, Andrea</creatorcontrib><creatorcontrib>Rangel-Yagui, Carlota Oliveira</creatorcontrib><creatorcontrib>Pasqualoto, Kerly Fernanda Mesquita</creatorcontrib><creatorcontrib>Tavares, Leoberto Costa</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>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jorge, Salomão Dória</au><au>Masunari, Andrea</au><au>Rangel-Yagui, Carlota Oliveira</au><au>Pasqualoto, Kerly Fernanda Mesquita</au><au>Tavares, Leoberto Costa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis, antimicrobial activity and molecular modeling studies of novel benzofuroxan derivatives against Staphylococcus aureus</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2009-04-15</date><risdate>2009</risdate><volume>17</volume><issue>8</issue><spage>3028</spage><epage>3036</epage><pages>3028-3036</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A new series of 14 4-substituted [
N′-(benzofuroxan-5-yl)methylene] benzohydrazides with structure analogous of nifuroxazide were synthesized and tested against standard and multidrug-resistant
Staphylococcus aureus strains.
Molecular modification is a quite promising strategy in the design and development of drug analogs with better bioavailability, higher intrinsic activity and less toxicity. In the search of new leads with potential antimicrobial activity, a new series of 14 4-substituted [
N′-(benzofuroxan-5-yl)methylene]benzohydrazides, nifuroxazide derivatives, were synthesized and tested against standard and multidrug-resistant
Staphylococcus aureus strains. The selection of the substituent groups was based on physicochemical properties, such as hydrophobicity and electronic effect. These properties were also evaluated through the lipophilic and electrostatic potential maps, respectively, considering the compounds with better biological profile. Twelve compounds exhibited similar bacteriostatic activity against standard and multidrug-resistant strains. The most active compound was the 4-CF
3 substituted derivative, which presented a minimum inhibitory concentration (MIC) value of 14.6–13.1
μg/mL, and a
Clog
P value of 1.87. The results highlight the benzofuroxan derivatives as potential leads for designing new future antimicrobial drug candidates.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19324556</pmid><doi>10.1016/j.bmc.2009.03.011</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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subjects | Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Benzofuroxan derivatives Benzoxazoles - chemical synthesis Benzoxazoles - chemistry Benzoxazoles - pharmacology Biological and medical sciences Drug Design Hydroxybenzoates - chemical synthesis Hydroxybenzoates - chemistry Hydroxybenzoates - pharmacology Medical sciences MIC Microbial Sensitivity Tests Models, Molecular Molecular modeling Molecular modification MRSA Nitrofurans - chemical synthesis Nitrofurans - chemistry Nitrofurans - pharmacology Pharmacology. Drug treatments Staphylococcus aureus Staphylococcus aureus - drug effects Structure-Activity Relationship VISA |
title | Design, synthesis, antimicrobial activity and molecular modeling studies of novel benzofuroxan derivatives against Staphylococcus aureus |
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