{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:26:34Z","timestamp":1760142394041,"version":"build-2065373602"},"reference-count":72,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2025,10,1]],"date-time":"2025-10-01T00:00:00Z","timestamp":1759276800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Cytisine, a naturally occurring alkaloid and partial agonist of nicotinic acetylcholine receptors (nAChRs), has long been used as a smoking cessation aid and serves as the pharmacophore for varenicline. Recent research has expanded its therapeutic scope to neurodegenerative and neurological disorders, motivating the development of new cytisine derivatives. Among these, N-propargylcytisine combines the biological activity of the parent compound with the synthetic versatility of the terminal alkyne group. Herein, we report the synthesis and characterization of N-propargylcytisine, and its symmetrical dimer linked through 1,3-diyne moiety obtained via a copper-mediated Glaser\u2013Hay oxidative coupling. The products were analyzed by NMR, FT-IR, and mass spectrometry, confirming the introduction of the propargyl moiety and the formation of the diyne bridge. Solvatochromic study of both compounds were performed using UV-VIS absorption spectroscopy in solvents of varying polarity, including protic solvents capable of hydrogen bonding. The 1,3-diyne motif, commonly found in bioactive natural products, endows the resulting dimer with potential for further derivatization and biological evaluation. This study demonstrates the utility of the Glaser\u2013Hay reaction in the functionalization of alkaloid scaffolds and highlights the prospects of N-propargylcytisine derivatives in drug discovery targeting the central nervous system.<\/jats:p>","DOI":"10.3390\/molecules30193955","type":"journal-article","created":{"date-parts":[[2025,10,2]],"date-time":"2025-10-02T08:20:28Z","timestamp":1759393228000},"page":"3955","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Copper-Mediated Homocoupling of N-propargylcytisine\u2014Synthesis and Spectral Characterization of Novel Cytisine-Based Diyne Dimer"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9106-8585","authenticated-orcid":false,"given":"Anna K.","family":"Przyby\u0142","sequence":"first","affiliation":[{"name":"Department of Medical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4770-215X","authenticated-orcid":false,"given":"Adam","family":"Huczy\u0144ski","sequence":"additional","affiliation":[{"name":"Department of Medical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ewa","family":"Krystkowiak","sequence":"additional","affiliation":[{"name":"Department of Spectroscopy and Magnetism, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,10,1]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"712","DOI":"10.1021\/cr400307e","article-title":"(\u2212)-Cytisine and Derivatives: Synthesis, Reactivity, and Applications","volume":"114","author":"Rouden","year":"2014","journal-title":"Chem. 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