Exploiting the Thiobarbituric Acid Scaffold for Antibacterial Activity
Thiobarbituric acid (TBA) has been considered a privileged structure for developing antimicrobial agents. Diversity was obtained at positions N and at C5 through acylation, Schiff base formation, Knoevenagel condensation, and thioamide and enamine formation. The present work describes the synthesis...
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| Veröffentlicht in: | ChemMedChem 2018-09, Vol.13 (18), p.1923-1930 |
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| creator | Sharma, Anamika Noki, Sikabwe Zamisa, Sizwe J. Hazzah, Heba A. Almarhoon, Zainab M. El‐Faham, Ayman de la Torre, Beatriz G. Albericio, Fernando |
| description | Thiobarbituric acid (TBA) has been considered a privileged structure for developing antimicrobial agents. Diversity was obtained at positions N and at C5 through acylation, Schiff base formation, Knoevenagel condensation, and thioamide and enamine formation. The present work describes the synthesis of small libraries based on the TBA moiety and above‐mentioned reactions. Preliminary antimicrobial activity screening of the prepared compounds against selected bacteria (both Gram‐positive and ‐negative) showed the best results for the Boc‐Phe‐TBA derivative. These results could be useful for designing and building libraries based on other amino acids with distinct protecting groups.
Antimicrobial analogue insight: Thiobarbituric acid (TBA) analogues with various functionalities at positions N and C5 were synthesized by acylation, Knoevenagel condensation, Schiff base, thioamide and enamine formation. They were then evaluated for antimicrobial activity, and Boc‐protected amino acid conjugates at position C5 with an ethyl‐substituted nitrogen atom were found to afford the best results; these could be useful in the design of future TBA‐based derivatives. |
| doi_str_mv | 10.1002/cmdc.201800414 |
| format | Article |
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Antimicrobial analogue insight: Thiobarbituric acid (TBA) analogues with various functionalities at positions N and C5 were synthesized by acylation, Knoevenagel condensation, Schiff base, thioamide and enamine formation. They were then evaluated for antimicrobial activity, and Boc‐protected amino acid conjugates at position C5 with an ethyl‐substituted nitrogen atom were found to afford the best results; these could be useful in the design of future TBA‐based derivatives.</description><identifier>ISSN: 1860-7179</identifier><identifier>EISSN: 1860-7187</identifier><identifier>DOI: 10.1002/cmdc.201800414</identifier><identifier>PMID: 30004647</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Acylation ; Amino acids ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibacterial activity ; antibiotics ; Antimicrobial activity ; Antimicrobial agents ; Bacillus subtilis - drug effects ; barbituric acid ; Dose-Response Relationship, Drug ; Escherichia coli - drug effects ; Imines ; Microbial Sensitivity Tests ; Molecular Structure ; nanoformulations ; Protecting groups ; Pseudomonas aeruginosa - drug effects ; Staphylococcus aureus - drug effects ; Structure-Activity Relationship ; Thiobarbiturates - chemical synthesis ; Thiobarbiturates - chemistry ; Thiobarbiturates - pharmacology ; Thiobarbituric acid</subject><ispartof>ChemMedChem, 2018-09, Vol.13 (18), p.1923-1930</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4134-47971faf2055caaade2f445435b417d8f9ebfc3f16fdb527b6c39c32a3d40fc93</citedby><cites>FETCH-LOGICAL-c4134-47971faf2055caaade2f445435b417d8f9ebfc3f16fdb527b6c39c32a3d40fc93</cites><orcidid>0000-0002-8946-0462</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcmdc.201800414$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcmdc.201800414$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30004647$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sharma, Anamika</creatorcontrib><creatorcontrib>Noki, Sikabwe</creatorcontrib><creatorcontrib>Zamisa, Sizwe J.</creatorcontrib><creatorcontrib>Hazzah, Heba A.</creatorcontrib><creatorcontrib>Almarhoon, Zainab M.</creatorcontrib><creatorcontrib>El‐Faham, Ayman</creatorcontrib><creatorcontrib>de la Torre, Beatriz G.</creatorcontrib><creatorcontrib>Albericio, Fernando</creatorcontrib><title>Exploiting the Thiobarbituric Acid Scaffold for Antibacterial Activity</title><title>ChemMedChem</title><addtitle>ChemMedChem</addtitle><description>Thiobarbituric acid (TBA) has been considered a privileged structure for developing antimicrobial agents. Diversity was obtained at positions N and at C5 through acylation, Schiff base formation, Knoevenagel condensation, and thioamide and enamine formation. The present work describes the synthesis of small libraries based on the TBA moiety and above‐mentioned reactions. Preliminary antimicrobial activity screening of the prepared compounds against selected bacteria (both Gram‐positive and ‐negative) showed the best results for the Boc‐Phe‐TBA derivative. These results could be useful for designing and building libraries based on other amino acids with distinct protecting groups.
Antimicrobial analogue insight: Thiobarbituric acid (TBA) analogues with various functionalities at positions N and C5 were synthesized by acylation, Knoevenagel condensation, Schiff base, thioamide and enamine formation. They were then evaluated for antimicrobial activity, and Boc‐protected amino acid conjugates at position C5 with an ethyl‐substituted nitrogen atom were found to afford the best results; these could be useful in the design of future TBA‐based derivatives.</description><subject>Acylation</subject><subject>Amino acids</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial activity</subject><subject>antibiotics</subject><subject>Antimicrobial activity</subject><subject>Antimicrobial agents</subject><subject>Bacillus subtilis - drug effects</subject><subject>barbituric acid</subject><subject>Dose-Response Relationship, Drug</subject><subject>Escherichia coli - drug effects</subject><subject>Imines</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>nanoformulations</subject><subject>Protecting groups</subject><subject>Pseudomonas aeruginosa - drug effects</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>Thiobarbiturates - chemical synthesis</subject><subject>Thiobarbiturates - chemistry</subject><subject>Thiobarbiturates - pharmacology</subject><subject>Thiobarbituric acid</subject><issn>1860-7179</issn><issn>1860-7187</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkDtPwzAURi0EoqWwMqJILCwpfiVOxiq0gFTEQJkt27GpqzyK7QD996RqKRIL0_2ke-6nqwPAJYJjBCG-VXWpxhiiDEKK6BEYoiyFMUMZOz5klg_AmferHqEZyk7BgMA-p5QNwWz6ta5aG2zzFoWljhZL20rhpA2dsyqaKFtGL0oY01ZlZFoXTZpgpVBBOyuqfh_shw2bc3BiROX1xX6OwOtsuige4vnz_WMxmceKIkJjynKGjDAYJokSQpQaG0oTShJJESszk2tpFDEoNaVMMJOpIrkiWJCSQqNyMgI3u961a9877QOvrVe6qkSj285zDBnEJEUI9-j1H3TVdq7pv-MYwSyjOUxJT413lHKt904bvna2Fm7DEeRbw3xrmB8M9wdX-9pO1ro84D9KeyDfAZ-20pt_6njxdFf8ln8Dy9uG4g</recordid><startdate>20180919</startdate><enddate>20180919</enddate><creator>Sharma, Anamika</creator><creator>Noki, Sikabwe</creator><creator>Zamisa, Sizwe J.</creator><creator>Hazzah, Heba A.</creator><creator>Almarhoon, Zainab M.</creator><creator>El‐Faham, Ayman</creator><creator>de la Torre, Beatriz G.</creator><creator>Albericio, Fernando</creator><general>Wiley Subscription Services, Inc</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>7QO</scope><scope>7TK</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>K9.</scope><scope>P64</scope><scope>RC3</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8946-0462</orcidid></search><sort><creationdate>20180919</creationdate><title>Exploiting the Thiobarbituric Acid Scaffold for Antibacterial Activity</title><author>Sharma, Anamika ; Noki, Sikabwe ; Zamisa, Sizwe J. ; Hazzah, Heba A. ; Almarhoon, Zainab M. ; El‐Faham, Ayman ; de la Torre, Beatriz G. ; Albericio, Fernando</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4134-47971faf2055caaade2f445435b417d8f9ebfc3f16fdb527b6c39c32a3d40fc93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acylation</topic><topic>Amino acids</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial activity</topic><topic>antibiotics</topic><topic>Antimicrobial activity</topic><topic>Antimicrobial agents</topic><topic>Bacillus subtilis - drug effects</topic><topic>barbituric acid</topic><topic>Dose-Response Relationship, Drug</topic><topic>Escherichia coli - drug effects</topic><topic>Imines</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>nanoformulations</topic><topic>Protecting groups</topic><topic>Pseudomonas aeruginosa - drug effects</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>Thiobarbiturates - chemical synthesis</topic><topic>Thiobarbiturates - chemistry</topic><topic>Thiobarbiturates - pharmacology</topic><topic>Thiobarbituric acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sharma, Anamika</creatorcontrib><creatorcontrib>Noki, Sikabwe</creatorcontrib><creatorcontrib>Zamisa, Sizwe J.</creatorcontrib><creatorcontrib>Hazzah, Heba A.</creatorcontrib><creatorcontrib>Almarhoon, Zainab M.</creatorcontrib><creatorcontrib>El‐Faham, Ayman</creatorcontrib><creatorcontrib>de la Torre, Beatriz G.</creatorcontrib><creatorcontrib>Albericio, Fernando</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>ChemMedChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sharma, Anamika</au><au>Noki, Sikabwe</au><au>Zamisa, Sizwe J.</au><au>Hazzah, Heba A.</au><au>Almarhoon, Zainab M.</au><au>El‐Faham, Ayman</au><au>de la Torre, Beatriz G.</au><au>Albericio, Fernando</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Exploiting the Thiobarbituric Acid Scaffold for Antibacterial Activity</atitle><jtitle>ChemMedChem</jtitle><addtitle>ChemMedChem</addtitle><date>2018-09-19</date><risdate>2018</risdate><volume>13</volume><issue>18</issue><spage>1923</spage><epage>1930</epage><pages>1923-1930</pages><issn>1860-7179</issn><eissn>1860-7187</eissn><abstract>Thiobarbituric acid (TBA) has been considered a privileged structure for developing antimicrobial agents. Diversity was obtained at positions N and at C5 through acylation, Schiff base formation, Knoevenagel condensation, and thioamide and enamine formation. The present work describes the synthesis of small libraries based on the TBA moiety and above‐mentioned reactions. Preliminary antimicrobial activity screening of the prepared compounds against selected bacteria (both Gram‐positive and ‐negative) showed the best results for the Boc‐Phe‐TBA derivative. These results could be useful for designing and building libraries based on other amino acids with distinct protecting groups.
Antimicrobial analogue insight: Thiobarbituric acid (TBA) analogues with various functionalities at positions N and C5 were synthesized by acylation, Knoevenagel condensation, Schiff base, thioamide and enamine formation. They were then evaluated for antimicrobial activity, and Boc‐protected amino acid conjugates at position C5 with an ethyl‐substituted nitrogen atom were found to afford the best results; these could be useful in the design of future TBA‐based derivatives.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30004647</pmid><doi>10.1002/cmdc.201800414</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-8946-0462</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Acylation Amino acids Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial activity antibiotics Antimicrobial activity Antimicrobial agents Bacillus subtilis - drug effects barbituric acid Dose-Response Relationship, Drug Escherichia coli - drug effects Imines Microbial Sensitivity Tests Molecular Structure nanoformulations Protecting groups Pseudomonas aeruginosa - drug effects Staphylococcus aureus - drug effects Structure-Activity Relationship Thiobarbiturates - chemical synthesis Thiobarbiturates - chemistry Thiobarbiturates - pharmacology Thiobarbituric acid |
| title | Exploiting the Thiobarbituric Acid Scaffold for Antibacterial Activity |
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