Azirine-containing dipeptides and depsipeptides: synthesis, transformations and antibacterial activity
Azirine-containing dipeptides and depsipeptides with a wide range of substituents have been synthesized in high yields via the Passerini and Ugi multicomponent reactions (MCRs) using 2 H -azirine-2-carboxylic acids as the acid component. The obtained MCR adducts have been transformed to lactam-fused...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2020-12, Vol.18 (46), p.9448-946 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Rostovskii, Nikolai V Koronatov, Alexander N Sakharov, Pavel A Agafonova, Anastasiya V Novikov, Mikhail S Khlebnikov, Alexander F Rogacheva, Elizaveta V Kraeva, Liudmila A |
| description | Azirine-containing dipeptides and depsipeptides with a wide range of substituents have been synthesized in high yields
via
the Passerini and Ugi multicomponent reactions (MCRs) using 2
H
-azirine-2-carboxylic acids as the acid component. The obtained MCR adducts have been transformed to lactam-fused aziridines, as well as pyrrole, imidazole, aziridine, and other derivatives, containing the dipeptide or depsipeptide moiety. The azirine-containing depsipeptides exhibit antibacterial activity against the ESKAPE pathogens, especially Gram-positive bacterial strains (
E. faecium
- MIC 16 μg mL
−1
,
S. aureus
- MIC 9 μg mL
−1
).
The Passerini and Ugi reactions with 2
H
-azirine-2-carboxylic acids gave novel antibacterial active 2
H
-azirines containing the dipeptide or depsipeptide moiety, which can be transformed to fused aziridines. |
| doi_str_mv | 10.1039/d0ob02023k |
| format | Article |
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via
the Passerini and Ugi multicomponent reactions (MCRs) using 2
H
-azirine-2-carboxylic acids as the acid component. The obtained MCR adducts have been transformed to lactam-fused aziridines, as well as pyrrole, imidazole, aziridine, and other derivatives, containing the dipeptide or depsipeptide moiety. The azirine-containing depsipeptides exhibit antibacterial activity against the ESKAPE pathogens, especially Gram-positive bacterial strains (
E. faecium
- MIC 16 μg mL
−1
,
S. aureus
- MIC 9 μg mL
−1
).
The Passerini and Ugi reactions with 2
H
-azirine-2-carboxylic acids gave novel antibacterial active 2
H
-azirines containing the dipeptide or depsipeptide moiety, which can be transformed to fused aziridines.</description><identifier>ISSN: 1477-0520</identifier><identifier>ISSN: 1477-0539</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d0ob02023k</identifier><identifier>PMID: 33170920</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Adducts ; Amides ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibacterial activity ; Azirines - chemical synthesis ; Azirines - chemistry ; Azirines - pharmacology ; Carboxylic acids ; Depsipeptides - chemical synthesis ; Depsipeptides - chemistry ; Depsipeptides - pharmacology ; Dipeptides - chemical synthesis ; Dipeptides - chemistry ; Dipeptides - pharmacology ; Enterococcus faecium - drug effects ; Imidazole ; Microbial Sensitivity Tests ; Minimum inhibitory concentration ; Molecular Structure ; Staphylococcus aureus - drug effects ; Structure-Activity Relationship</subject><ispartof>Organic & biomolecular chemistry, 2020-12, Vol.18 (46), p.9448-946</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-257e5fd58e0a01f3007ef97a23045d91e4dcdc3053536695b0588150914f8fd43</citedby><cites>FETCH-LOGICAL-c337t-257e5fd58e0a01f3007ef97a23045d91e4dcdc3053536695b0588150914f8fd43</cites><orcidid>0000-0002-6100-0309 ; 0000-0003-1855-7440 ; 0000-0002-8925-794X ; 0000-0002-5184-4890 ; 0000-0001-7746-7387</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33170920$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rostovskii, Nikolai V</creatorcontrib><creatorcontrib>Koronatov, Alexander N</creatorcontrib><creatorcontrib>Sakharov, Pavel A</creatorcontrib><creatorcontrib>Agafonova, Anastasiya V</creatorcontrib><creatorcontrib>Novikov, Mikhail S</creatorcontrib><creatorcontrib>Khlebnikov, Alexander F</creatorcontrib><creatorcontrib>Rogacheva, Elizaveta V</creatorcontrib><creatorcontrib>Kraeva, Liudmila A</creatorcontrib><title>Azirine-containing dipeptides and depsipeptides: synthesis, transformations and antibacterial activity</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Azirine-containing dipeptides and depsipeptides with a wide range of substituents have been synthesized in high yields
via
the Passerini and Ugi multicomponent reactions (MCRs) using 2
H
-azirine-2-carboxylic acids as the acid component. The obtained MCR adducts have been transformed to lactam-fused aziridines, as well as pyrrole, imidazole, aziridine, and other derivatives, containing the dipeptide or depsipeptide moiety. The azirine-containing depsipeptides exhibit antibacterial activity against the ESKAPE pathogens, especially Gram-positive bacterial strains (
E. faecium
- MIC 16 μg mL
−1
,
S. aureus
- MIC 9 μg mL
−1
).
The Passerini and Ugi reactions with 2
H
-azirine-2-carboxylic acids gave novel antibacterial active 2
H
-azirines containing the dipeptide or depsipeptide moiety, which can be transformed to fused aziridines.</description><subject>Adducts</subject><subject>Amides</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>Azirines - chemical synthesis</subject><subject>Azirines - chemistry</subject><subject>Azirines - pharmacology</subject><subject>Carboxylic acids</subject><subject>Depsipeptides - chemical synthesis</subject><subject>Depsipeptides - chemistry</subject><subject>Depsipeptides - pharmacology</subject><subject>Dipeptides - chemical synthesis</subject><subject>Dipeptides - chemistry</subject><subject>Dipeptides - pharmacology</subject><subject>Enterococcus faecium - drug effects</subject><subject>Imidazole</subject><subject>Microbial Sensitivity Tests</subject><subject>Minimum inhibitory concentration</subject><subject>Molecular Structure</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Structure-Activity Relationship</subject><issn>1477-0520</issn><issn>1477-0539</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0U1PAyEQBmBiNNavi3fNJl6McXWAZVm81foZm_Si5w1dQNGWXYGa1F8v2loTT0zgyWR4B6F9DGcYqDhX0I6BAKFva2gLF5znwKhYX9UEemg7hFcALHhZbKIepZiDILCFTP_Teut03rQuSuuse86U7XQXrdIhk05lSndhdXORhbmLLzrYcJpFL10wrZ_KaFu30NJFO5ZN1N7KSZYK-2HjfBdtGDkJem957qCnm-vHwV0-HN3eD_rDvKGUx5wwrplRrNIgARsKwLURXBIKBVMC60I1qqHpe4yWpWBjYFWFGQhcmMqogu6g40XfzrfvMx1iPbWh0ZOJdLqdhZoUTJSEMeCJHv2jr-3MuzRdUmXKiZKiSupkoRrfhuC1qTtvp9LPawz1d_r1FYwuf9J_SPhw2XI2nmq1or9xJ3CwAD40q9e_9dEvRcaJwg</recordid><startdate>20201207</startdate><enddate>20201207</enddate><creator>Rostovskii, Nikolai V</creator><creator>Koronatov, Alexander N</creator><creator>Sakharov, Pavel A</creator><creator>Agafonova, Anastasiya V</creator><creator>Novikov, Mikhail S</creator><creator>Khlebnikov, Alexander F</creator><creator>Rogacheva, Elizaveta V</creator><creator>Kraeva, Liudmila A</creator><general>Royal Society of Chemistry</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>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6100-0309</orcidid><orcidid>https://orcid.org/0000-0003-1855-7440</orcidid><orcidid>https://orcid.org/0000-0002-8925-794X</orcidid><orcidid>https://orcid.org/0000-0002-5184-4890</orcidid><orcidid>https://orcid.org/0000-0001-7746-7387</orcidid></search><sort><creationdate>20201207</creationdate><title>Azirine-containing dipeptides and depsipeptides: synthesis, transformations and antibacterial activity</title><author>Rostovskii, Nikolai V ; Koronatov, Alexander N ; Sakharov, Pavel A ; Agafonova, Anastasiya V ; Novikov, Mikhail S ; Khlebnikov, Alexander F ; Rogacheva, Elizaveta V ; Kraeva, Liudmila A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-257e5fd58e0a01f3007ef97a23045d91e4dcdc3053536695b0588150914f8fd43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Adducts</topic><topic>Amides</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>Azirines - chemical synthesis</topic><topic>Azirines - chemistry</topic><topic>Azirines - pharmacology</topic><topic>Carboxylic acids</topic><topic>Depsipeptides - chemical synthesis</topic><topic>Depsipeptides - chemistry</topic><topic>Depsipeptides - pharmacology</topic><topic>Dipeptides - chemical synthesis</topic><topic>Dipeptides - chemistry</topic><topic>Dipeptides - pharmacology</topic><topic>Enterococcus faecium - drug effects</topic><topic>Imidazole</topic><topic>Microbial Sensitivity Tests</topic><topic>Minimum inhibitory concentration</topic><topic>Molecular Structure</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rostovskii, Nikolai V</creatorcontrib><creatorcontrib>Koronatov, Alexander N</creatorcontrib><creatorcontrib>Sakharov, Pavel A</creatorcontrib><creatorcontrib>Agafonova, Anastasiya V</creatorcontrib><creatorcontrib>Novikov, Mikhail S</creatorcontrib><creatorcontrib>Khlebnikov, Alexander F</creatorcontrib><creatorcontrib>Rogacheva, Elizaveta V</creatorcontrib><creatorcontrib>Kraeva, Liudmila 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>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rostovskii, Nikolai V</au><au>Koronatov, Alexander N</au><au>Sakharov, Pavel A</au><au>Agafonova, Anastasiya V</au><au>Novikov, Mikhail S</au><au>Khlebnikov, Alexander F</au><au>Rogacheva, Elizaveta V</au><au>Kraeva, Liudmila A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Azirine-containing dipeptides and depsipeptides: synthesis, transformations and antibacterial activity</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2020-12-07</date><risdate>2020</risdate><volume>18</volume><issue>46</issue><spage>9448</spage><epage>946</epage><pages>9448-946</pages><issn>1477-0520</issn><issn>1477-0539</issn><eissn>1477-0539</eissn><abstract>Azirine-containing dipeptides and depsipeptides with a wide range of substituents have been synthesized in high yields
via
the Passerini and Ugi multicomponent reactions (MCRs) using 2
H
-azirine-2-carboxylic acids as the acid component. The obtained MCR adducts have been transformed to lactam-fused aziridines, as well as pyrrole, imidazole, aziridine, and other derivatives, containing the dipeptide or depsipeptide moiety. The azirine-containing depsipeptides exhibit antibacterial activity against the ESKAPE pathogens, especially Gram-positive bacterial strains (
E. faecium
- MIC 16 μg mL
−1
,
S. aureus
- MIC 9 μg mL
−1
).
The Passerini and Ugi reactions with 2
H
-azirine-2-carboxylic acids gave novel antibacterial active 2
H
-azirines containing the dipeptide or depsipeptide moiety, which can be transformed to fused aziridines.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>33170920</pmid><doi>10.1039/d0ob02023k</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0002-6100-0309</orcidid><orcidid>https://orcid.org/0000-0003-1855-7440</orcidid><orcidid>https://orcid.org/0000-0002-8925-794X</orcidid><orcidid>https://orcid.org/0000-0002-5184-4890</orcidid><orcidid>https://orcid.org/0000-0001-7746-7387</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2020-12, Vol.18 (46), p.9448-946 |
| issn | 1477-0520 1477-0539 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2459625507 |
| source | MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Adducts Amides Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial activity Azirines - chemical synthesis Azirines - chemistry Azirines - pharmacology Carboxylic acids Depsipeptides - chemical synthesis Depsipeptides - chemistry Depsipeptides - pharmacology Dipeptides - chemical synthesis Dipeptides - chemistry Dipeptides - pharmacology Enterococcus faecium - drug effects Imidazole Microbial Sensitivity Tests Minimum inhibitory concentration Molecular Structure Staphylococcus aureus - drug effects Structure-Activity Relationship |
| title | Azirine-containing dipeptides and depsipeptides: synthesis, transformations and antibacterial activity |
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