Synthesis and Intramolecular Cyclization of 2,3-Seco-Lupane Triterpenoids with an Ethylketone Fragment
A 1-cyano-2,3-secolupane derivative with an ethylketone fragment was synthesized from 2-hydroxyoximodihydrobetulonic acid methyl ester via a Grignard reaction followed by a Beckmann rearrangement and was used further to prepare α -bromo-substituted diastereomers. Nitrile-anionic cyclization of the e...
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| Veröffentlicht in: | Chemistry of natural compounds 2023, Vol.59 (1), p.94-98 |
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| creator | Galaiko, N. V. Beloglazova, Yu. A. Grishko, V. V. |
| description | A 1-cyano-2,3-secolupane derivative with an ethylketone fragment was synthesized from 2-hydroxyoximodihydrobetulonic acid methyl ester via a Grignard reaction followed by a Beckmann rearrangement and was used further to prepare
α
-bromo-substituted diastereomers. Nitrile-anionic cyclization of the ethylketone and
α
-bromo isomers produced cyclic derivatives with an alkenenitrile and an
α,β
-unsaturated ketone in ring A, respectively. The obtained compounds did not exhibit cytotoxic activity according to biological screening data. |
| doi_str_mv | 10.1007/s10600-023-03925-9 |
| format | Article |
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α
-bromo-substituted diastereomers. Nitrile-anionic cyclization of the ethylketone and
α
-bromo isomers produced cyclic derivatives with an alkenenitrile and an
α,β
-unsaturated ketone in ring A, respectively. The obtained compounds did not exhibit cytotoxic activity according to biological screening data.</description><identifier>ISSN: 0009-3130</identifier><identifier>EISSN: 1573-8388</identifier><identifier>DOI: 10.1007/s10600-023-03925-9</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Biological activity ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; cyclization reactions ; cytotoxicity ; diastereomers ; Grignard reactions ; Ketones ; Organic Chemistry ; Plant Sciences ; triterpenoids</subject><ispartof>Chemistry of natural compounds, 2023, Vol.59 (1), p.94-98</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><rights>COPYRIGHT 2023 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c376t-93d78dd00f631e0eb6d5720fe1e9683299893f3a69563988f0e8f92870e6d7163</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/s10600-023-03925-9$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10600-023-03925-9$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Galaiko, N. V.</creatorcontrib><creatorcontrib>Beloglazova, Yu. A.</creatorcontrib><creatorcontrib>Grishko, V. V.</creatorcontrib><title>Synthesis and Intramolecular Cyclization of 2,3-Seco-Lupane Triterpenoids with an Ethylketone Fragment</title><title>Chemistry of natural compounds</title><addtitle>Chem Nat Compd</addtitle><description>A 1-cyano-2,3-secolupane derivative with an ethylketone fragment was synthesized from 2-hydroxyoximodihydrobetulonic acid methyl ester via a Grignard reaction followed by a Beckmann rearrangement and was used further to prepare
α
-bromo-substituted diastereomers. Nitrile-anionic cyclization of the ethylketone and
α
-bromo isomers produced cyclic derivatives with an alkenenitrile and an
α,β
-unsaturated ketone in ring A, respectively. The obtained compounds did not exhibit cytotoxic activity according to biological screening data.</description><subject>Biological activity</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>cyclization reactions</subject><subject>cytotoxicity</subject><subject>diastereomers</subject><subject>Grignard reactions</subject><subject>Ketones</subject><subject>Organic Chemistry</subject><subject>Plant Sciences</subject><subject>triterpenoids</subject><issn>0009-3130</issn><issn>1573-8388</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kVFrFDEUhYNYcK39Az4N-KJg6s1kJ5M8lqXVhQXBbZ9DOnOzmzqTrEkGXX-92U5B6oPkISR853DuPYS8ZXDJANpPiYEAoFBzClzVDVUvyII1LaeSS_mSLABAUc44vCKvU3ooTymEXBC7Pfq8x-RSZXxfrX2OZgwDdtNgYrU6doP7bbILvgq2qj9yusUu0M10MB6r2-gyxgP64PpU_XR5X0yq67w_Dt8xh0LcRLMb0ec35MyaIeHF031O7m6ub1df6Obr5_XqakM73opMFe9b2fcAVnCGgPeib9oaLDJUQvJaKam45UaoRnAlpQWUVtWyBRR9ywQ_J-9n30MMPyZMWY8udTgMJW6YkuawhGWxYcuCvvsHfQhT9CWdriWTcimAsUJdztTODKidt6EsqCunx9F1ZUTryv9V25z239Qn2w_PBIXJ-CvvzJSSXm-_PWfrme1iSCmi1YfoRhOPmoE-9arnXnXpVT_2qlUR8VmUCux3GP_m_o_qDy5Hoy4</recordid><startdate>2023</startdate><enddate>2023</enddate><creator>Galaiko, N. V.</creator><creator>Beloglazova, Yu. A.</creator><creator>Grishko, V. V.</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>ISR</scope><scope>7S9</scope><scope>L.6</scope></search><sort><creationdate>2023</creationdate><title>Synthesis and Intramolecular Cyclization of 2,3-Seco-Lupane Triterpenoids with an Ethylketone Fragment</title><author>Galaiko, N. V. ; Beloglazova, Yu. A. ; Grishko, V. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c376t-93d78dd00f631e0eb6d5720fe1e9683299893f3a69563988f0e8f92870e6d7163</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Biological activity</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>cyclization reactions</topic><topic>cytotoxicity</topic><topic>diastereomers</topic><topic>Grignard reactions</topic><topic>Ketones</topic><topic>Organic Chemistry</topic><topic>Plant Sciences</topic><topic>triterpenoids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Galaiko, N. V.</creatorcontrib><creatorcontrib>Beloglazova, Yu. A.</creatorcontrib><creatorcontrib>Grishko, V. V.</creatorcontrib><collection>CrossRef</collection><collection>Gale In Context: Science</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Chemistry of natural compounds</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Galaiko, N. V.</au><au>Beloglazova, Yu. A.</au><au>Grishko, V. V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Intramolecular Cyclization of 2,3-Seco-Lupane Triterpenoids with an Ethylketone Fragment</atitle><jtitle>Chemistry of natural compounds</jtitle><stitle>Chem Nat Compd</stitle><date>2023</date><risdate>2023</risdate><volume>59</volume><issue>1</issue><spage>94</spage><epage>98</epage><pages>94-98</pages><issn>0009-3130</issn><eissn>1573-8388</eissn><abstract>A 1-cyano-2,3-secolupane derivative with an ethylketone fragment was synthesized from 2-hydroxyoximodihydrobetulonic acid methyl ester via a Grignard reaction followed by a Beckmann rearrangement and was used further to prepare
α
-bromo-substituted diastereomers. Nitrile-anionic cyclization of the ethylketone and
α
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α,β
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| subjects | Biological activity Chemistry Chemistry and Materials Science Chemistry/Food Science cyclization reactions cytotoxicity diastereomers Grignard reactions Ketones Organic Chemistry Plant Sciences triterpenoids |
| title | Synthesis and Intramolecular Cyclization of 2,3-Seco-Lupane Triterpenoids with an Ethylketone Fragment |
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