Synthesis of 4-(N-cycloalkylamino)-substituted polyfluorobenzoic acids and their esters
When treated with cycloalkylamines (pyrrolidine, piperidine, morpholine, and N -methylpiperazine), polyfluoro-containing benzoic and salicylic acid esters undergo chemoselective nucleophilic aromatic substitution of a fluorine atom in the para position to form 4-( N -cycloalkylamino)-substituted der...
Gespeichert in:
| Veröffentlicht in: | Russian chemical bulletin 2024-07, Vol.73 (7), p.1984-1995 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1995 |
|---|---|
| container_issue | 7 |
| container_start_page | 1984 |
| container_title | Russian chemical bulletin |
| container_volume | 73 |
| creator | Baranovskiy, A. D. Shchegolkov, E. V. Burgart, Ya. V. Krasnykh, O. P. Malysheva, K. O. Gerasimova, N. A. Evstigneeva, N. P. Saloutin, V. I. |
| description | When treated with cycloalkylamines (pyrrolidine, piperidine, morpholine, and
N
-methylpiperazine), polyfluoro-containing benzoic and salicylic acid esters undergo chemoselective nucleophilic aromatic substitution of a fluorine atom in the
para
position to form 4-(
N
-cycloalkylamino)-substituted derivatives. The hydrolysis of the latter compounds with alkali in aqueous methanol affords the corresponding acids. Methyl 3,5-difluoro-2-hydroxy-4-(piperidin-1-yl)benzoate exhibits high antibacterial activity against the
N. gonorrhoeae
strain, which is twice higher than that of the drug spectinomycin.
N
-Cycloalkyl-substituted polyfluorobenzoic acids do not show analgesic activity. The effect of the esters is comparable with the activity of the drug diclofenac. The studied compounds have a lower acute toxicity compared to the reference drug. |
| doi_str_mv | 10.1007/s11172-024-4318-3 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_3099283103</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3099283103</sourcerecordid><originalsourceid>FETCH-LOGICAL-c198t-8ae4a6a8ea642150aac4b99ec20b55fad91f72bef2120c8d2c821ed76cc954c3</originalsourceid><addsrcrecordid>eNp1kE1LxDAURYMoOI7-AHcFN7qI5qVNmyxl8AsGXTjgMqRpqhk7Tc1rF_XX26GCK1fvLe65Fw4h58CugbHiBgGg4JTxjGYpSJoekAWIIqUKCjicfpbnVHApjskJ4pYxxqWUC_L2Orb9h0OPSaiTjF4-UzvaJpjmc2zMzrfhiuJQYu_7oXdV0oVmrJshxFC69jt4mxjrK0xMWyVTj4-Jw95FPCVHtWnQnf3eJdnc321Wj3T98vC0ul1TC0r2VBqXmdxIZ_KMg2DG2KxUylnOSiFqUymoC166mgNnVlbcSg6uKnJrlchsuiQXc20Xw9cwTettGGI7LeqUKcVlCiydUjCnbAyI0dW6i35n4qiB6b0-PevTkz6916f3DJ8ZnLLtu4t_zf9DPzpsc-Y</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3099283103</pqid></control><display><type>article</type><title>Synthesis of 4-(N-cycloalkylamino)-substituted polyfluorobenzoic acids and their esters</title><source>Springer Nature - Complete Springer Journals</source><creator>Baranovskiy, A. D. ; Shchegolkov, E. V. ; Burgart, Ya. V. ; Krasnykh, O. P. ; Malysheva, K. O. ; Gerasimova, N. A. ; Evstigneeva, N. P. ; Saloutin, V. I.</creator><creatorcontrib>Baranovskiy, A. D. ; Shchegolkov, E. V. ; Burgart, Ya. V. ; Krasnykh, O. P. ; Malysheva, K. O. ; Gerasimova, N. A. ; Evstigneeva, N. P. ; Saloutin, V. I.</creatorcontrib><description>When treated with cycloalkylamines (pyrrolidine, piperidine, morpholine, and
N
-methylpiperazine), polyfluoro-containing benzoic and salicylic acid esters undergo chemoselective nucleophilic aromatic substitution of a fluorine atom in the
para
position to form 4-(
N
-cycloalkylamino)-substituted derivatives. The hydrolysis of the latter compounds with alkali in aqueous methanol affords the corresponding acids. Methyl 3,5-difluoro-2-hydroxy-4-(piperidin-1-yl)benzoate exhibits high antibacterial activity against the
N. gonorrhoeae
strain, which is twice higher than that of the drug spectinomycin.
N
-Cycloalkyl-substituted polyfluorobenzoic acids do not show analgesic activity. The effect of the esters is comparable with the activity of the drug diclofenac. The studied compounds have a lower acute toxicity compared to the reference drug.</description><identifier>ISSN: 1066-5285</identifier><identifier>EISSN: 1573-9171</identifier><identifier>DOI: 10.1007/s11172-024-4318-3</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Benzoates ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Esters ; Fluorine ; Full Articles ; Inorganic Chemistry ; Organic Chemistry ; Piperidine ; Salicylic acid ; Substitutes</subject><ispartof>Russian chemical bulletin, 2024-07, Vol.73 (7), p.1984-1995</ispartof><rights>Springer Science+Business Media LLC 2024</rights><rights>Springer Science+Business Media LLC 2024.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c198t-8ae4a6a8ea642150aac4b99ec20b55fad91f72bef2120c8d2c821ed76cc954c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11172-024-4318-3$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11172-024-4318-3$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Baranovskiy, A. D.</creatorcontrib><creatorcontrib>Shchegolkov, E. V.</creatorcontrib><creatorcontrib>Burgart, Ya. V.</creatorcontrib><creatorcontrib>Krasnykh, O. P.</creatorcontrib><creatorcontrib>Malysheva, K. O.</creatorcontrib><creatorcontrib>Gerasimova, N. A.</creatorcontrib><creatorcontrib>Evstigneeva, N. P.</creatorcontrib><creatorcontrib>Saloutin, V. I.</creatorcontrib><title>Synthesis of 4-(N-cycloalkylamino)-substituted polyfluorobenzoic acids and their esters</title><title>Russian chemical bulletin</title><addtitle>Russ Chem Bull</addtitle><description>When treated with cycloalkylamines (pyrrolidine, piperidine, morpholine, and
N
-methylpiperazine), polyfluoro-containing benzoic and salicylic acid esters undergo chemoselective nucleophilic aromatic substitution of a fluorine atom in the
para
position to form 4-(
N
-cycloalkylamino)-substituted derivatives. The hydrolysis of the latter compounds with alkali in aqueous methanol affords the corresponding acids. Methyl 3,5-difluoro-2-hydroxy-4-(piperidin-1-yl)benzoate exhibits high antibacterial activity against the
N. gonorrhoeae
strain, which is twice higher than that of the drug spectinomycin.
N
-Cycloalkyl-substituted polyfluorobenzoic acids do not show analgesic activity. The effect of the esters is comparable with the activity of the drug diclofenac. The studied compounds have a lower acute toxicity compared to the reference drug.</description><subject>Benzoates</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Esters</subject><subject>Fluorine</subject><subject>Full Articles</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><subject>Piperidine</subject><subject>Salicylic acid</subject><subject>Substitutes</subject><issn>1066-5285</issn><issn>1573-9171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kE1LxDAURYMoOI7-AHcFN7qI5qVNmyxl8AsGXTjgMqRpqhk7Tc1rF_XX26GCK1fvLe65Fw4h58CugbHiBgGg4JTxjGYpSJoekAWIIqUKCjicfpbnVHApjskJ4pYxxqWUC_L2Orb9h0OPSaiTjF4-UzvaJpjmc2zMzrfhiuJQYu_7oXdV0oVmrJshxFC69jt4mxjrK0xMWyVTj4-Jw95FPCVHtWnQnf3eJdnc321Wj3T98vC0ul1TC0r2VBqXmdxIZ_KMg2DG2KxUylnOSiFqUymoC166mgNnVlbcSg6uKnJrlchsuiQXc20Xw9cwTettGGI7LeqUKcVlCiydUjCnbAyI0dW6i35n4qiB6b0-PevTkz6916f3DJ8ZnLLtu4t_zf9DPzpsc-Y</recordid><startdate>20240701</startdate><enddate>20240701</enddate><creator>Baranovskiy, A. D.</creator><creator>Shchegolkov, E. V.</creator><creator>Burgart, Ya. V.</creator><creator>Krasnykh, O. P.</creator><creator>Malysheva, K. O.</creator><creator>Gerasimova, N. A.</creator><creator>Evstigneeva, N. P.</creator><creator>Saloutin, V. I.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20240701</creationdate><title>Synthesis of 4-(N-cycloalkylamino)-substituted polyfluorobenzoic acids and their esters</title><author>Baranovskiy, A. D. ; Shchegolkov, E. V. ; Burgart, Ya. V. ; Krasnykh, O. P. ; Malysheva, K. O. ; Gerasimova, N. A. ; Evstigneeva, N. P. ; Saloutin, V. I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c198t-8ae4a6a8ea642150aac4b99ec20b55fad91f72bef2120c8d2c821ed76cc954c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Benzoates</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Esters</topic><topic>Fluorine</topic><topic>Full Articles</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Piperidine</topic><topic>Salicylic acid</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Baranovskiy, A. D.</creatorcontrib><creatorcontrib>Shchegolkov, E. V.</creatorcontrib><creatorcontrib>Burgart, Ya. V.</creatorcontrib><creatorcontrib>Krasnykh, O. P.</creatorcontrib><creatorcontrib>Malysheva, K. O.</creatorcontrib><creatorcontrib>Gerasimova, N. A.</creatorcontrib><creatorcontrib>Evstigneeva, N. P.</creatorcontrib><creatorcontrib>Saloutin, V. I.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian chemical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Baranovskiy, A. D.</au><au>Shchegolkov, E. V.</au><au>Burgart, Ya. V.</au><au>Krasnykh, O. P.</au><au>Malysheva, K. O.</au><au>Gerasimova, N. A.</au><au>Evstigneeva, N. P.</au><au>Saloutin, V. I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 4-(N-cycloalkylamino)-substituted polyfluorobenzoic acids and their esters</atitle><jtitle>Russian chemical bulletin</jtitle><stitle>Russ Chem Bull</stitle><date>2024-07-01</date><risdate>2024</risdate><volume>73</volume><issue>7</issue><spage>1984</spage><epage>1995</epage><pages>1984-1995</pages><issn>1066-5285</issn><eissn>1573-9171</eissn><abstract>When treated with cycloalkylamines (pyrrolidine, piperidine, morpholine, and
N
-methylpiperazine), polyfluoro-containing benzoic and salicylic acid esters undergo chemoselective nucleophilic aromatic substitution of a fluorine atom in the
para
position to form 4-(
N
-cycloalkylamino)-substituted derivatives. The hydrolysis of the latter compounds with alkali in aqueous methanol affords the corresponding acids. Methyl 3,5-difluoro-2-hydroxy-4-(piperidin-1-yl)benzoate exhibits high antibacterial activity against the
N. gonorrhoeae
strain, which is twice higher than that of the drug spectinomycin.
N
-Cycloalkyl-substituted polyfluorobenzoic acids do not show analgesic activity. The effect of the esters is comparable with the activity of the drug diclofenac. The studied compounds have a lower acute toxicity compared to the reference drug.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s11172-024-4318-3</doi><tpages>12</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1066-5285 |
| ispartof | Russian chemical bulletin, 2024-07, Vol.73 (7), p.1984-1995 |
| issn | 1066-5285 1573-9171 |
| language | eng |
| recordid | cdi_proquest_journals_3099283103 |
| source | Springer Nature - Complete Springer Journals |
| subjects | Benzoates Chemistry Chemistry and Materials Science Chemistry/Food Science Esters Fluorine Full Articles Inorganic Chemistry Organic Chemistry Piperidine Salicylic acid Substitutes |
| title | Synthesis of 4-(N-cycloalkylamino)-substituted polyfluorobenzoic acids and their esters |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-01T01%3A25%3A55IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%204-(N-cycloalkylamino)-substituted%20polyfluorobenzoic%20acids%20and%20their%20esters&rft.jtitle=Russian%20chemical%20bulletin&rft.au=Baranovskiy,%20A.%20D.&rft.date=2024-07-01&rft.volume=73&rft.issue=7&rft.spage=1984&rft.epage=1995&rft.pages=1984-1995&rft.issn=1066-5285&rft.eissn=1573-9171&rft_id=info:doi/10.1007/s11172-024-4318-3&rft_dat=%3Cproquest_cross%3E3099283103%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=3099283103&rft_id=info:pmid/&rfr_iscdi=true |