Click Synthesis of 1,2,3-Triazole Nucleosides Based on Functionalized Nicotinonitriles
A facile synthesis of a new series of 1,2,3-triazolyl nucleosides via one-pot click reaction is described. Acetylenic nicotinonitriles synthesized previously by alkylation of 4,6-diaryl-2-oxonicotinonitriles with propargyl bromide were involved in cycloaddition with 2,3,4,6-tetra- O -acetyl-D-glucop...
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| Veröffentlicht in: | Russian journal of organic chemistry 2020, Vol.56 (1), p.143-147 |
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| container_title | Russian journal of organic chemistry |
| container_volume | 56 |
| creator | Morsy, H. A. Mohammed, S. M. Abdel Hamid, A. M. Moustafa, A. H. El-Sayed, H. A. |
| description | A facile synthesis of a new series of 1,2,3-triazolyl nucleosides via one-pot click reaction is described. Acetylenic nicotinonitriles synthesized previously by alkylation of 4,6-diaryl-2-oxonicotinonitriles with propargyl bromide were involved in cycloaddition with 2,3,4,6-tetra-
O
-acetyl-D-glucopyranosyl azide in the presence of copper(I) to afford 1,2,3-triazole derivatives which were deprotected by treatment with aqueous triethylamine. The obtained 1,2,3-triazole nucleosides showed significant antimicrobial activities against some Gram-positive and Gram-negative bacteria and fungi. |
| doi_str_mv | 10.1134/S1070428020010224 |
| format | Article |
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O
-acetyl-D-glucopyranosyl azide in the presence of copper(I) to afford 1,2,3-triazole derivatives which were deprotected by treatment with aqueous triethylamine. The obtained 1,2,3-triazole nucleosides showed significant antimicrobial activities against some Gram-positive and Gram-negative bacteria and fungi.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428020010224</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Alkylation ; Chemical reactions ; Chemistry ; Chemistry and Materials Science ; Cycloaddition ; Nucleosides ; Organic Chemistry ; Triazoles ; Triethylamine</subject><ispartof>Russian journal of organic chemistry, 2020, Vol.56 (1), p.143-147</ispartof><rights>Pleiades Publishing, Ltd. 2020</rights><rights>2020© Pleiades Publishing, Ltd. 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-3556d128dfa63f3be93f2901cb32b0efee84a41cddbb556a9b2f53a0764a5d183</citedby><cites>FETCH-LOGICAL-c316t-3556d128dfa63f3be93f2901cb32b0efee84a41cddbb556a9b2f53a0764a5d183</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070428020010224$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428020010224$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27923,27924,41487,42556,51318</link.rule.ids></links><search><creatorcontrib>Morsy, H. A.</creatorcontrib><creatorcontrib>Mohammed, S. M.</creatorcontrib><creatorcontrib>Abdel Hamid, A. M.</creatorcontrib><creatorcontrib>Moustafa, A. H.</creatorcontrib><creatorcontrib>El-Sayed, H. A.</creatorcontrib><title>Click Synthesis of 1,2,3-Triazole Nucleosides Based on Functionalized Nicotinonitriles</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>A facile synthesis of a new series of 1,2,3-triazolyl nucleosides via one-pot click reaction is described. Acetylenic nicotinonitriles synthesized previously by alkylation of 4,6-diaryl-2-oxonicotinonitriles with propargyl bromide were involved in cycloaddition with 2,3,4,6-tetra-
O
-acetyl-D-glucopyranosyl azide in the presence of copper(I) to afford 1,2,3-triazole derivatives which were deprotected by treatment with aqueous triethylamine. The obtained 1,2,3-triazole nucleosides showed significant antimicrobial activities against some Gram-positive and Gram-negative bacteria and fungi.</description><subject>Alkylation</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Cycloaddition</subject><subject>Nucleosides</subject><subject>Organic Chemistry</subject><subject>Triazoles</subject><subject>Triethylamine</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1kDFPwzAQhS0EEqXwA9gisTZw53PTZISKAlJVhhbWyHFscAlxsZOh_fW4KhIDYrrTve89nR5jlwjXiCRulggTEDwHDoDAuThiA8wgT4kKOo57lNO9fsrOQlgDgEBBA_Y6baz6SJbbtnvXwYbEmQRHfETpylu5c41OFr1qtAu21iG5k0HXiWuTWd-qzrpWNnYXLwurXGdb19rO20aHc3ZiZBP0xc8cspfZ_Wr6mM6fH56mt_NUEWZdSuNxViPPayMzMlTpggwvAFVFvAJttM6FFKjquqoiKouKmzFJmGRCjmvMaciuDrkb7756Hbpy7Xofvwolp0leCAEZRAoPlPIuBK9NufH2U_ptiVDu6yv_1Bc9_OAJkW3ftP9N_t_0DQTKcNE</recordid><startdate>2020</startdate><enddate>2020</enddate><creator>Morsy, H. A.</creator><creator>Mohammed, S. M.</creator><creator>Abdel Hamid, A. M.</creator><creator>Moustafa, A. H.</creator><creator>El-Sayed, H. A.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>2020</creationdate><title>Click Synthesis of 1,2,3-Triazole Nucleosides Based on Functionalized Nicotinonitriles</title><author>Morsy, H. A. ; Mohammed, S. M. ; Abdel Hamid, A. M. ; Moustafa, A. H. ; El-Sayed, H. A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-3556d128dfa63f3be93f2901cb32b0efee84a41cddbb556a9b2f53a0764a5d183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkylation</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Cycloaddition</topic><topic>Nucleosides</topic><topic>Organic Chemistry</topic><topic>Triazoles</topic><topic>Triethylamine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Morsy, H. A.</creatorcontrib><creatorcontrib>Mohammed, S. M.</creatorcontrib><creatorcontrib>Abdel Hamid, A. M.</creatorcontrib><creatorcontrib>Moustafa, A. H.</creatorcontrib><creatorcontrib>El-Sayed, H. A.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Morsy, H. A.</au><au>Mohammed, S. M.</au><au>Abdel Hamid, A. M.</au><au>Moustafa, A. H.</au><au>El-Sayed, H. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Click Synthesis of 1,2,3-Triazole Nucleosides Based on Functionalized Nicotinonitriles</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2020</date><risdate>2020</risdate><volume>56</volume><issue>1</issue><spage>143</spage><epage>147</epage><pages>143-147</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>A facile synthesis of a new series of 1,2,3-triazolyl nucleosides via one-pot click reaction is described. Acetylenic nicotinonitriles synthesized previously by alkylation of 4,6-diaryl-2-oxonicotinonitriles with propargyl bromide were involved in cycloaddition with 2,3,4,6-tetra-
O
-acetyl-D-glucopyranosyl azide in the presence of copper(I) to afford 1,2,3-triazole derivatives which were deprotected by treatment with aqueous triethylamine. The obtained 1,2,3-triazole nucleosides showed significant antimicrobial activities against some Gram-positive and Gram-negative bacteria and fungi.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1070428020010224</doi><tpages>5</tpages></addata></record> |
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| language | eng |
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| subjects | Alkylation Chemical reactions Chemistry Chemistry and Materials Science Cycloaddition Nucleosides Organic Chemistry Triazoles Triethylamine |
| title | Click Synthesis of 1,2,3-Triazole Nucleosides Based on Functionalized Nicotinonitriles |
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