Synthesis and Biological Activity of 2,6-Substituted Pyridoxine Derivatives. Unusual Catalytic Role of Selenium Dioxide in the Formation of Pyridinone Methides
Among the seven-membered ketals of pyridoxine containing hydroxymethyl groups in various positions of the pyridine ring, an unusual ability of selenium dioxide to catalyze the reaction of nucleophilic substitution of the hydroxyl group by N , O -nucleophiles was found. Quantum chemical calculations...
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Veröffentlicht in: | Russian journal of general chemistry 2024-08, Vol.94 (8), p.1912-1929 |
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container_end_page | 1929 |
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container_issue | 8 |
container_start_page | 1912 |
container_title | Russian journal of general chemistry |
container_volume | 94 |
creator | Khaziev, R. M. Platonova, E. A. Bondar, O. V. Khristolyubova, A. S. Serov, N. Y. Lisovskaya, S. A. Vafina, R. M. Shtyrlin, V. G. Shtyrlin, N. V. Islamov, D. R. Burilov, V. A. Romanova, E. I. Shtyrlin, Yu. G. |
description | Among the seven-membered ketals of pyridoxine containing hydroxymethyl groups in various positions of the pyridine ring, an unusual ability of selenium dioxide to catalyze the reaction of nucleophilic substitution of the hydroxyl group by
N
,
O
-nucleophiles was found. Quantum chemical calculations have shown the possibility of the formation of selenium dioxide adducts with substrates and the formation of reactive intermediates—
ortho-
and
para-
pyridinone methides. The antioxidant and antimycotic activity of the obtained compounds was determined. |
doi_str_mv | 10.1134/S1070363224080036 |
format | Article |
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N
,
O
-nucleophiles was found. Quantum chemical calculations have shown the possibility of the formation of selenium dioxide adducts with substrates and the formation of reactive intermediates—
ortho-
and
para-
pyridinone methides. The antioxidant and antimycotic activity of the obtained compounds was determined.</description><identifier>ISSN: 1070-3632</identifier><identifier>EISSN: 1608-3350</identifier><identifier>DOI: 10.1134/S1070363224080036</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Adducts ; Biological activity ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Dioxides ; Hydroxyl groups ; Nucleophiles ; Pyridoxine ; Quantum chemistry ; Selenium dioxide ; Substitution reactions ; Substrates</subject><ispartof>Russian journal of general chemistry, 2024-08, Vol.94 (8), p.1912-1929</ispartof><rights>Pleiades Publishing, Ltd. 2024</rights><rights>Pleiades Publishing, Ltd. 2024.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c198t-b96533fc98beb94305422505d02ffec8dc177b5fe1647b5fdae2adb8105a49943</cites><orcidid>0000-0003-4820-884X ; 0000-0001-7089-3340 ; 0000-0002-4377-2567 ; 0000-0002-2777-719X ; 0000-0001-7926-5121 ; 0000-0002-3306-2668 ; 0000-0002-5772-8399 ; 0000-0002-5988-1012 ; 0000-0001-9856-5664 ; 0000-0002-2968-8887</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070363224080036$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070363224080036$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Khaziev, R. M.</creatorcontrib><creatorcontrib>Platonova, E. A.</creatorcontrib><creatorcontrib>Bondar, O. V.</creatorcontrib><creatorcontrib>Khristolyubova, A. S.</creatorcontrib><creatorcontrib>Serov, N. Y.</creatorcontrib><creatorcontrib>Lisovskaya, S. A.</creatorcontrib><creatorcontrib>Vafina, R. M.</creatorcontrib><creatorcontrib>Shtyrlin, V. G.</creatorcontrib><creatorcontrib>Shtyrlin, N. V.</creatorcontrib><creatorcontrib>Islamov, D. R.</creatorcontrib><creatorcontrib>Burilov, V. A.</creatorcontrib><creatorcontrib>Romanova, E. I.</creatorcontrib><creatorcontrib>Shtyrlin, Yu. G.</creatorcontrib><title>Synthesis and Biological Activity of 2,6-Substituted Pyridoxine Derivatives. Unusual Catalytic Role of Selenium Dioxide in the Formation of Pyridinone Methides</title><title>Russian journal of general chemistry</title><addtitle>Russ J Gen Chem</addtitle><description>Among the seven-membered ketals of pyridoxine containing hydroxymethyl groups in various positions of the pyridine ring, an unusual ability of selenium dioxide to catalyze the reaction of nucleophilic substitution of the hydroxyl group by
N
,
O
-nucleophiles was found. Quantum chemical calculations have shown the possibility of the formation of selenium dioxide adducts with substrates and the formation of reactive intermediates—
ortho-
and
para-
pyridinone methides. The antioxidant and antimycotic activity of the obtained compounds was determined.</description><subject>Adducts</subject><subject>Biological activity</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Dioxides</subject><subject>Hydroxyl groups</subject><subject>Nucleophiles</subject><subject>Pyridoxine</subject><subject>Quantum chemistry</subject><subject>Selenium dioxide</subject><subject>Substitution reactions</subject><subject>Substrates</subject><issn>1070-3632</issn><issn>1608-3350</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kdtKxDAQhosoeHwA7wLeWs2h7baXuh5BUax7XdJmupulm2iSLvZpfFWnruCFeDUD833_wEwUHTN6xphIzktGJ1RkgvOE5hS7rWiPZTSPhUjpNvY4jsf5brTv_ZJSRmnG96LPcjBhAV57Io0il9p2dq4b2ZGLJui1DgOxLeGnWVz2tQ869AEUeR6cVvZDGyBX4PRaIgr-jMxM73t0pzLIbgi6IS-2gzGhhA6M7lfkSqOngGhDcC-5sW6FtjUj9B2rjcXYRwgLxPxhtNPKzsPRTz2IZjfXr9O7-OHp9n568RA3rMhDXBdZKkTbFHkNdZEImiacpzRVlLctNLlq2GRSpy2wLBmrksClqnNGU5kUKBxEJ5vcN2ffe_ChWtreGVxZCTwww_tNUqTYhmqc9d5BW705vZJuqBitxj9Uf_6ADt84HlkzB_eb_L_0Beeii_A</recordid><startdate>20240801</startdate><enddate>20240801</enddate><creator>Khaziev, R. 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N
,
O
-nucleophiles was found. Quantum chemical calculations have shown the possibility of the formation of selenium dioxide adducts with substrates and the formation of reactive intermediates—
ortho-
and
para-
pyridinone methides. The antioxidant and antimycotic activity of the obtained compounds was determined.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1070363224080036</doi><tpages>18</tpages><orcidid>https://orcid.org/0000-0003-4820-884X</orcidid><orcidid>https://orcid.org/0000-0001-7089-3340</orcidid><orcidid>https://orcid.org/0000-0002-4377-2567</orcidid><orcidid>https://orcid.org/0000-0002-2777-719X</orcidid><orcidid>https://orcid.org/0000-0001-7926-5121</orcidid><orcidid>https://orcid.org/0000-0002-3306-2668</orcidid><orcidid>https://orcid.org/0000-0002-5772-8399</orcidid><orcidid>https://orcid.org/0000-0002-5988-1012</orcidid><orcidid>https://orcid.org/0000-0001-9856-5664</orcidid><orcidid>https://orcid.org/0000-0002-2968-8887</orcidid></addata></record> |
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subjects | Adducts Biological activity Chemical synthesis Chemistry Chemistry and Materials Science Chemistry/Food Science Dioxides Hydroxyl groups Nucleophiles Pyridoxine Quantum chemistry Selenium dioxide Substitution reactions Substrates |
title | Synthesis and Biological Activity of 2,6-Substituted Pyridoxine Derivatives. Unusual Catalytic Role of Selenium Dioxide in the Formation of Pyridinone Methides |
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