Synthesis, structure, and biological activity of novel heterocyclic sulfonyl-carboximidamides
A series of novel heterocyclic sulfonyl-carboximidamides were synthesized in satisfactory yields via condensation of heterocyclic methyl carbimidates with 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide. New structures were confirmed by IR and NMR spectra as well as elemental analyses....
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| Veröffentlicht in: | Monatshefte für Chemie 2013, Vol.144 (5), p.647-658 |
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| container_title | Monatshefte für Chemie |
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| creator | Gobis, Katarzyna Foks, Henryk Sławiński, Jarosław Sikorski, Artur Trzybiński, Damian Augustynowicz-Kopeć, Ewa Napiórkowska, Agnieszka Bojanowski, Krzysztof |
| description | A series of novel heterocyclic sulfonyl-carboximidamides were synthesized in satisfactory yields via condensation of heterocyclic methyl carbimidates with 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide. New structures were confirmed by IR and NMR spectra as well as elemental analyses. X-ray crystallography of two derivatives was performed. The single-crystal structures confirmed the presence of a primary amine group in the amidine moiety. All the compounds were screened for their tuberculostatic, antibacterial, and anticancer activities. Preliminary results indicated that target compounds exhibited weak tuberculostatic and antibacterial activities. Seven compounds inhibited the growth of some cancer cell lines, whereas one of the 2-quinoline derivatives displayed favorable activity against all tested cancer cells with
GI
50
values of 0.92–13 μM.
Graphical abstract
|
| doi_str_mv | 10.1007/s00706-012-0888-0 |
| format | Article |
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GI
50
values of 0.92–13 μM.
Graphical abstract
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GI
50
values of 0.92–13 μM.
Graphical abstract
</description><subject>Analytical Chemistry</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Theoretical and Computational Chemistry</subject><issn>0026-9247</issn><issn>1434-4475</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>C6C</sourceid><recordid>eNp9kctuFDEQRS0EIsPAB7BBvWQRk_Jj-rFBQhEvKVIWCUtk2dXuGUceO9juUfrv8WhCBBsWLsuqW7eufAh5y-ADA-guci3QUmCcQt_3FJ6RFZNCUim7zXOyAuAtHbjszsirnO-gviWIl-SMt6xt-56tyM-bJZSdzS6fN7mkGcuc7Hmjw9gYF33cOtS-0VjcwZWliVMT4sH6ZmeLTREX9A6bPPsphsVT1MnEB7d3o67H5tfkxaR9tm8e7zX58eXz7eU3enX99fvlpyuKUvJCLba8G6Q2mo-DQWkAtWAt2mmQmx4Go1vJhZVGjIPmzHajMIgomDDQggaxJh9Pvvez2dsRbShJe3Wf3F6nRUXt1L-d4HZqGw9KykF2HasG7x8NUvw121zU3mW03utg45wV6zdDB4zVGGvCTlJMMedkp6c1DNQRizphURWLOmJRx3zv_s73NPGHQxXwkyDXVtjapO7inEL9s_-4_gbAqJvN</recordid><startdate>2013</startdate><enddate>2013</enddate><creator>Gobis, Katarzyna</creator><creator>Foks, Henryk</creator><creator>Sławiński, Jarosław</creator><creator>Sikorski, Artur</creator><creator>Trzybiński, Damian</creator><creator>Augustynowicz-Kopeć, Ewa</creator><creator>Napiórkowska, Agnieszka</creator><creator>Bojanowski, Krzysztof</creator><general>Springer Vienna</general><scope>C6C</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>2013</creationdate><title>Synthesis, structure, and biological activity of novel heterocyclic sulfonyl-carboximidamides</title><author>Gobis, Katarzyna ; Foks, Henryk ; Sławiński, Jarosław ; Sikorski, Artur ; Trzybiński, Damian ; Augustynowicz-Kopeć, Ewa ; Napiórkowska, Agnieszka ; Bojanowski, Krzysztof</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c442t-ec62794aba2d9bc4b0ca316cef945809ba6423e4b3d9a21e7d3bccc313b060a03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Analytical Chemistry</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Theoretical and Computational Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gobis, Katarzyna</creatorcontrib><creatorcontrib>Foks, Henryk</creatorcontrib><creatorcontrib>Sławiński, Jarosław</creatorcontrib><creatorcontrib>Sikorski, Artur</creatorcontrib><creatorcontrib>Trzybiński, Damian</creatorcontrib><creatorcontrib>Augustynowicz-Kopeć, Ewa</creatorcontrib><creatorcontrib>Napiórkowska, Agnieszka</creatorcontrib><creatorcontrib>Bojanowski, Krzysztof</creatorcontrib><collection>Springer Nature OA Free Journals</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Monatshefte für Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gobis, Katarzyna</au><au>Foks, Henryk</au><au>Sławiński, Jarosław</au><au>Sikorski, Artur</au><au>Trzybiński, Damian</au><au>Augustynowicz-Kopeć, Ewa</au><au>Napiórkowska, Agnieszka</au><au>Bojanowski, Krzysztof</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, structure, and biological activity of novel heterocyclic sulfonyl-carboximidamides</atitle><jtitle>Monatshefte für Chemie</jtitle><stitle>Monatsh Chem</stitle><addtitle>Monatsh Chem</addtitle><date>2013</date><risdate>2013</risdate><volume>144</volume><issue>5</issue><spage>647</spage><epage>658</epage><pages>647-658</pages><issn>0026-9247</issn><eissn>1434-4475</eissn><abstract>A series of novel heterocyclic sulfonyl-carboximidamides were synthesized in satisfactory yields via condensation of heterocyclic methyl carbimidates with 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide. New structures were confirmed by IR and NMR spectra as well as elemental analyses. X-ray crystallography of two derivatives was performed. The single-crystal structures confirmed the presence of a primary amine group in the amidine moiety. All the compounds were screened for their tuberculostatic, antibacterial, and anticancer activities. Preliminary results indicated that target compounds exhibited weak tuberculostatic and antibacterial activities. Seven compounds inhibited the growth of some cancer cell lines, whereas one of the 2-quinoline derivatives displayed favorable activity against all tested cancer cells with
GI
50
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Graphical abstract
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| subjects | Analytical Chemistry Chemistry Chemistry and Materials Science Chemistry/Food Science Inorganic Chemistry Organic Chemistry Original Paper Physical Chemistry Theoretical and Computational Chemistry |
| title | Synthesis, structure, and biological activity of novel heterocyclic sulfonyl-carboximidamides |
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