{"id":726,"date":"2022-10-27T18:27:38","date_gmt":"2022-10-27T16:27:38","guid":{"rendered":"https:\/\/labmedchem.unipv.it\/?p=726"},"modified":"2025-07-04T12:50:07","modified_gmt":"2025-07-04T10:50:07","slug":"from-nature-to-synthetic-compounds-novel-1n23-trisubstituted-5-oxopyrrolidines-targeting-multiple-myeloma-cells","status":"publish","type":"post","link":"https:\/\/labmedchem.unipv.it\/index.php\/2022\/10\/27\/from-nature-to-synthetic-compounds-novel-1n23-trisubstituted-5-oxopyrrolidines-targeting-multiple-myeloma-cells\/","title":{"rendered":"1,3-Dithiolane as a Privileged Scaffold in Bioactive Derivatives: Chiral Resolution and Assignment of Absolute Configuration"},"content":{"rendered":"\n<p><strong>Listro, R.; Rossino, G.; Cavalloro, V.; Rossi, D.; Boiocchi, M.; Robescu, M.S.; Bavaro, T.; Franchini, S.; Sorbi, C.; De Amici, M.; Linciano, P.; Collina, S.<\/strong><\/p>\n\n\n\n<p>(2024)\u00a0<em>Int. J. Mol. Sci.<\/em>,\u00a025, 12880<\/p>\n\n\n\n<p>DOI:&nbsp;<a href=\"https:\/\/doi.org\/10.3390\/ijms252312880\">10.3390\/ijms252312880<\/a><\/p>\n\n\n\n<p>ABSTRACT: The 1,3-dithiolane ring has been recently rehabilitated as a chemical scaffold in drug design. However, for derivatives that are substituted in position 4, the introduction of a chiral center on the heterocycle demands the separation and characterization of the stereoisomers. We report the first chiral resolution and absolute configuration (AC) assignment for (1,4-dithiaspiro[4.5]decan-2-yl)methanol (<em>R\/S<\/em>)-<strong>1<\/strong>, a key synthon for dithiolane-based biologically active compounds. Using (semi)preparative enantioselective HPLC, we isolated enantiomeric\u00a0<strong>1<\/strong>. The AC was assigned by using (+)-<strong>1<\/strong>\u00a0for the enantioselective synthesis of (+)-<strong>BS148<\/strong>, a sigma receptor modulator. An X-ray diffraction analysis established the (<em>R<\/em>)-configuration of (+)-<strong>BS148<\/strong>\u00a0and, by extension, of (<em>+<\/em>)-<strong>1<\/strong>. This method provides a reliable approach for preparing enantiopure 1,3-dithiolane scaffolds and establishes reference standards for AC determination of related compounds.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Listro, R.; Rossino, G.; Cavalloro, V.; Rossi, D.; Boiocchi, M.; Robescu, M.S.; Bavaro, T.; Franchini, S.; Sorbi, C.; De Amici, M.; Linciano, P.; Collina, S.<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":[],"categories":[6],"tags":[21,67],"_links":{"self":[{"href":"https:\/\/labmedchem.unipv.it\/index.php\/wp-json\/wp\/v2\/posts\/726"}],"collection":[{"href":"https:\/\/labmedchem.unipv.it\/index.php\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/labmedchem.unipv.it\/index.php\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/labmedchem.unipv.it\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/labmedchem.unipv.it\/index.php\/wp-json\/wp\/v2\/comments?post=726"}],"version-history":[{"count":5,"href":"https:\/\/labmedchem.unipv.it\/index.php\/wp-json\/wp\/v2\/posts\/726\/revisions"}],"predecessor-version":[{"id":1019,"href":"https:\/\/labmedchem.unipv.it\/index.php\/wp-json\/wp\/v2\/posts\/726\/revisions\/1019"}],"wp:attachment":[{"href":"https:\/\/labmedchem.unipv.it\/index.php\/wp-json\/wp\/v2\/media?parent=726"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/labmedchem.unipv.it\/index.php\/wp-json\/wp\/v2\/categories?post=726"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/labmedchem.unipv.it\/index.php\/wp-json\/wp\/v2\/tags?post=726"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}