{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,2]],"date-time":"2025-11-02T06:40:41Z","timestamp":1762065641216,"version":"build-2065373602"},"reference-count":58,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2022,9,8]],"date-time":"2022-09-08T00:00:00Z","timestamp":1662595200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Hungarian Research Foundation","award":["NKFI K138871","20391-3\/2018\/FEKUSTRAT","TKP2021-EGA-32","TKP2021-EGA"],"award-info":[{"award-number":["NKFI K138871","20391-3\/2018\/FEKUSTRAT","TKP2021-EGA-32","TKP2021-EGA"]}]},{"name":"Ministry of Human Capacities, Hungary","award":["NKFI K138871","20391-3\/2018\/FEKUSTRAT","TKP2021-EGA-32","TKP2021-EGA"],"award-info":[{"award-number":["NKFI K138871","20391-3\/2018\/FEKUSTRAT","TKP2021-EGA-32","TKP2021-EGA"]}]},{"DOI":"10.13039\/501100012550","name":"Ministry of Innovation and Technology of Hungary from the National Research, Development, and Innovation Fund","doi-asserted-by":"publisher","award":["NKFI K138871","20391-3\/2018\/FEKUSTRAT","TKP2021-EGA-32","TKP2021-EGA"],"award-info":[{"award-number":["NKFI K138871","20391-3\/2018\/FEKUSTRAT","TKP2021-EGA-32","TKP2021-EGA"]}],"id":[{"id":"10.13039\/501100012550","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>A series of gibberellic acid-based aminodiols was designed and synthesized from commercially available gibberellic acid. Exposure of gibberellic acid to hydrochloric acid under reflux conditions resulted in aromatization followed by rearrangement to form allo-gibberic acid. The key intermediate, ethyl allo-gibberate, was prepared according to literature methods. Epoxidation of key intermediate and subsequent ring-opening of the corresponding epoxide with different nucleophiles resulted in N-substituted aminodiols. The regioselective ring closure of N-benzyl-substituted aminodiol with formaldehyde was also investigated. All aminodiol derivatives were well characterized using modern spectroscopic techniques and evaluated for their antiproliferative activity against a panel of human cancer cell lines. In addition, structure\u2013activity relationships were examined by assessing substituent effects on the aminodiol systems. The results indicated that aminodiols containing aromatic rings on their nitrogen substituents displayed significant cytotoxic effects. Among these agents, N-naphthylmethyl-substituted aminodiols were found to be the most potent candidates in this series. One of these molecules exhibited a modest cancer selectivity determined by non-cancerous fibroblast cells. A docking study was also made to exploit the observed results.<\/jats:p>","DOI":"10.3390\/ijms231810366","type":"journal-article","created":{"date-parts":[[2022,9,8]],"date-time":"2022-09-08T07:05:56Z","timestamp":1662620756000},"page":"10366","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Stereoselective Synthesis and Application of Gibberellic Acid-Derived Aminodiols"],"prefix":"10.3390","volume":"23","author":[{"given":"Zein Alabdeen","family":"Khdar","sequence":"first","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary Excellent Center, E\u00f6tv\u00f6s utca 6, H-6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8296-887X","authenticated-orcid":false,"given":"Tam Minh","family":"Le","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary Excellent Center, E\u00f6tv\u00f6s utca 6, H-6720 Szeged, Hungary"},{"name":"Stereochemistry Research Group of the Hungarian Academy of Sciences, E\u00f6tv\u00f6s utca 6, H-6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8519-4830","authenticated-orcid":false,"given":"Zsuzsanna","family":"Schelz","sequence":"additional","affiliation":[{"name":"Institute of Pharmacodynamics and Biopharmacy, University of Szeged, Interdisciplinary Excellent Center, H-6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3243-5300","authenticated-orcid":false,"given":"Istv\u00e1n","family":"Zupk\u00f3","sequence":"additional","affiliation":[{"name":"Institute of Pharmacodynamics and Biopharmacy, University of Szeged, Interdisciplinary Excellent Center, H-6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2432-8409","authenticated-orcid":false,"given":"Zsolt","family":"Szakonyi","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary Excellent Center, E\u00f6tv\u00f6s utca 6, H-6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,9,8]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1605","DOI":"10.1021\/np000765k","article-title":"Natural Compounds in Cancer Therapy: Promising Nontoxic Antitumor Agents from Plants and Other Natural Sources","volume":"64","author":"Kroll","year":"2001","journal-title":"J. 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