{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,30]],"date-time":"2026-06-30T10:50:15Z","timestamp":1782816615234,"version":"3.54.5"},"reference-count":54,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2024,12,29]],"date-time":"2024-12-29T00:00:00Z","timestamp":1735430400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006595","name":"Ministry of Research, Innovation, and Digitization, CNCS-UEFISCDI","doi-asserted-by":"publisher","award":["PN-IV-P8-8.3-ROMD-2023-0045"],"award-info":[{"award-number":["PN-IV-P8-8.3-ROMD-2023-0045"]}],"id":[{"id":"10.13039\/501100006595","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Azulene-1,3-bis(semicarbazone), 1, and azulene-1,3-bis(thiosemicarbazone), 2, were synthesized by the acid-catalyzed condensation reactions of semicarbazide and thiosemicarbazide, respectively, with azulene-1,3-dicarboxaldehyde in stoichiometric amounts. Compounds 1 and 2 were identified by high-resolution mass spectrometry and characterized by IR, 1H-NMR, 13C-NMR, and UV-vis spectroscopic techniques. Crystal structure determination of azulene-1,3-bis(thiosemicarbazone) shows that the thiosemicarbazone units exhibit a syn-closed conformation, with both arms oriented in the same direction and adopting an E configuration with respect to the imine linkages. Both hydrazones are redox active and showed fluorescence emission at 450 nm upon excitation at 350 nm. The bis-semicarbazone showed no affinity for anions nor for mercury(II) metal cation. Instead, the bis-thiosemicarbazone showed a lower affinity for chloride anions, but enhanced affinity for binding\/poisoning Hg2+ ions. Both compounds were tested against osteosarcoma MG63 cell lines, exhibiting low antiproliferative activity with comparable IC50 values of 473.08 \u03bcM and 472.40 \u03bcM for compounds 1 and 2, respectively. Despite this limited antiproliferative effect, further analysis using propidium iodide staining revealed a concentration-dependent decrease in cell viability, with high concentrations inducing a marked reduction in cell number, accompanied by morphological changes characteristic of apoptosis and necrosis.<\/jats:p>","DOI":"10.3390\/molecules30010083","type":"journal-article","created":{"date-parts":[[2025,1,1]],"date-time":"2025-01-01T14:35:42Z","timestamp":1735742142000},"page":"83","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Synthesis, Physicochemical Properties, and Ion Recognition Ability of Azulene-Based Bis-(Thio)Semicarbazone"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0433-752X","authenticated-orcid":false,"given":"Anamaria","family":"Hanganu","sequence":"first","affiliation":[{"name":"\u201cC. D. Nenitzescu\u201d Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania"},{"name":"Faculty of Chemistry, University of Bucharest, 4-12 Bvd. Regina Elisabeta, 030018 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6033-3710","authenticated-orcid":false,"given":"Catalin","family":"Maxim","sequence":"additional","affiliation":[{"name":"\u201cC. D. Nenitzescu\u201d Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania"},{"name":"Faculty of Chemistry, University of Bucharest, 4-12 Bvd. Regina Elisabeta, 030018 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andreea","family":"Dogaru","sequence":"additional","affiliation":[{"name":"\u201cC. D. Nenitzescu\u201d Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adrian E.","family":"Ion","sequence":"additional","affiliation":[{"name":"\u201cC. D. Nenitzescu\u201d Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9031-338X","authenticated-orcid":false,"given":"Coralia","family":"Bleotu","sequence":"additional","affiliation":[{"name":"Stefan S. Nicolau Institute of Virology, 285 Mihai Bravu Avenue, 030317 Bucharest, Romania"},{"name":"Department of Botany and Microbiology, Faculty of Biology, University of Bucharest, 1-3 Aleea Portocalelor, 060101 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Augustin M.","family":"Madalan","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Bucharest, 4-12 Bvd. Regina Elisabeta, 030018 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniela","family":"Bala","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Bucharest, 4-12 Bvd. Regina Elisabeta, 030018 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Simona","family":"Nica","sequence":"additional","affiliation":[{"name":"\u201cC. D. Nenitzescu\u201d Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,12,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"702","DOI":"10.1039\/D0CS00861C","article-title":"Two-photon small-molecule fluorescence-based agents for sensing, imaging, and therapy within biological systems","volume":"50","author":"Wu","year":"2021","journal-title":"Chem. Soc. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2775","DOI":"10.1016\/j.tet.2018.04.043","article-title":"Azulene\u2014Thiophene\u2014Cyanoacrylic acid dyes with donor-\u03c0-acceptor structures. 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