{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,8]],"date-time":"2026-01-08T00:22:46Z","timestamp":1767831766364,"version":"3.49.0"},"reference-count":65,"publisher":"MDPI AG","issue":"20","license":[{"start":{"date-parts":[[2022,10,20]],"date-time":"2022-10-20T00:00:00Z","timestamp":1666224000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["22-73-10184"],"award-info":[{"award-number":["22-73-10184"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The 1,3-dipolar cycloaddition of 2-(2-oxoindoline-3-ylidene)acetates with functionalized aldo- and ketonitrones proceeds with good selectivity to provide new highly functionalized 5-spiroisoxazolidines. A characteristic feature of these reactions is reversibility that allows for the control of the diastereoselectivity of cycloaddition. The reduction of obtained adducts using zinc powder in acetic acid leads to 1,3-aminoalcohols or spirolactones. For a number of the spiro compounds obtained, anticancer activity was found.<\/jats:p>","DOI":"10.3390\/ijms232012639","type":"journal-article","created":{"date-parts":[[2022,10,20]],"date-time":"2022-10-20T22:49:46Z","timestamp":1666306186000},"page":"12639","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3500-4610","authenticated-orcid":false,"given":"Dmitriy D.","family":"Karcev","sequence":"first","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9277-6185","authenticated-orcid":false,"given":"Mariia M.","family":"Efremova","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexander P.","family":"Molchanov","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8925-794X","authenticated-orcid":false,"given":"Nikolai V.","family":"Rostovskii","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mariya A.","family":"Kryukova","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6408-8329","authenticated-orcid":false,"given":"Alexander S.","family":"Bunev","sequence":"additional","affiliation":[{"name":"Medicinal Chemistry Center, Togliatti State University, Belorusskaya st. 14, 445020 Togliatti, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5694-3492","authenticated-orcid":false,"given":"Dmitry A.","family":"Khochenkov","sequence":"additional","affiliation":[{"name":"Medicinal Chemistry Center, Togliatti State University, Belorusskaya st. 14, 445020 Togliatti, Russia"},{"name":"Blokhin National Medical Center of Oncology, Kashirskoe Shosse 24, 115478 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,10,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3673","DOI":"10.1016\/j.bmcl.2014.06.081","article-title":"The use of spirocyclic scaffolds in drug discovery","volume":"24","author":"Zheng","year":"2014","journal-title":"Bioorg. 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