{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T04:32:40Z","timestamp":1789446760285,"version":"build-2803163510"},"reference-count":70,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2025,11,10]],"date-time":"2025-11-10T00:00:00Z","timestamp":1762732800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Science Committee of the Ministry of Science and Higher Education of the Republic of Kazakhstan","award":["AP19674667"],"award-info":[{"award-number":["AP19674667"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The year 2024 marked the 80th anniversary of Woodward\u2019s total synthesis of quinine. Quinine is a natural alkaloid from the bark of the cinchona tree that has been used for years as an antimalarial drug. The antibacterial effect of quinine salts has also been regarded. With this in mind, a series of original 9-deoxycinchone alkaloid derivatives bearing a dialkylamino- or heterocyclic moiety at the 4 position of the 9-(((4-X-but-2-ynyloxy)methyl)-1,2,3-triazolyl)-substituent was synthesized. The copper-catalyzed three-component A3-coupling reaction of 9-(((4-prop-2-ynyloxy)methyl)-1,2,3-triazolyl)- substituted cinchona alkaloid derivatives with secondary amines and formaldehyde was the main route of synthesis. The present study attempted to examine the antibacterial properties of 9-substituted 9-desoxyquinine-derived compounds and their antibacterial activity against pathogenic bacterial strains, e.g., Staphylococcus aureus, Bacillus subtillis, Bacillus cereus, and Escherichia coli. The difference in the antibacterial activity profile of diastereoisomeric 9-(((4-X-but-2-ynyloxy)methyl)-1,2,3-triazolyl)-substituted derivatives of cinchona alkaloids indicated the importance of the nature of nitrogen substituents in the molecules. In a concentration-dependent pattern, (9R)- and (9S)- (((4-asocan-1yl)-but-2-ynyl-oxy)methyl)-1,2,3-triazolyl)-substituted compounds demonstrated considerable biofilm-inhibitory efficacy against the S. aureus bacterial strain. A detailed study of the molecular interactions with the targeted protein MurB was performed using docking simulations, and the obtained results are quite promising.<\/jats:p>","DOI":"10.3390\/molecules30224352","type":"journal-article","created":{"date-parts":[[2025,11,10]],"date-time":"2025-11-10T17:45:34Z","timestamp":1762796734000},"page":"4352","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Synthesis, Antibacterial Properties and Molecular Docking Studies of Nitrogen Substituted 9-(((4X-But-2-ynyloxy)methyl)-1,2,3-triazolyl)\u2013Cinchona Alkaloid Conjugates"],"prefix":"10.3390","volume":"30","author":[{"given":"Gulim K.","family":"Mukusheva","sequence":"first","affiliation":[{"name":"Chemistry Faculty, Karaganda National Research University Buketov, Karaganda 100024, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nurizat N.","family":"Toigambekova","sequence":"additional","affiliation":[{"name":"Chemistry Faculty, Karaganda National Research University Buketov, Karaganda 100024, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Victor A.","family":"Savelyev","sequence":"additional","affiliation":[{"name":"Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3022-4510","authenticated-orcid":false,"given":"Andrey I.","family":"Khlebnikov","sequence":"additional","affiliation":[{"name":"Kizhner Research Center, Tomsk Polytechnic University, Tomsk 634050, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liubov G.","family":"Burova","sequence":"additional","affiliation":[{"name":"Department of Microbiology, Immunology and Virology, Novosibirsk State Medical University, Krasny Prospect 52, Novosibirsk 630091, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-6963-4503","authenticated-orcid":false,"given":"Sofiia D.","family":"Afanaseva","sequence":"additional","affiliation":[{"name":"Department of Microbiology, Immunology and Virology, Novosibirsk State Medical University, Krasny Prospect 52, Novosibirsk 630091, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1878-2787","authenticated-orcid":false,"given":"Oralgazy A.","family":"Nurkenov","sequence":"additional","affiliation":[{"name":"Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Karaganda 100008, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9169-3492","authenticated-orcid":false,"given":"Anarkul S.","family":"Kishkentayeva","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Karaganda Medical University, Karaganda 100012, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aikerim S.","family":"Olzhabayeva","sequence":"additional","affiliation":[{"name":"Chemistry Faculty, Karaganda National Research University Buketov, Karaganda 100024, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4128-7293","authenticated-orcid":false,"given":"Yurii V.","family":"Gatilov","sequence":"additional","affiliation":[{"name":"Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roza B.","family":"Seidakhmetova","sequence":"additional","affiliation":[{"name":"Department of Clinical Pharmacology and Evidence-Based Medicine, Karaganda Medical University, Karaganda 100012, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander N.","family":"Evstropov","sequence":"additional","affiliation":[{"name":"Department of Microbiology, Immunology and Virology, Novosibirsk State Medical University, Krasny Prospect 52, Novosibirsk 630091, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0761-9696","authenticated-orcid":false,"given":"Elvira E.","family":"Shults","sequence":"additional","affiliation":[{"name":"Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,11,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"854","DOI":"10.1002\/anie.200400663","article-title":"The quest for quinine:Those who won the battles and those who won the war","volume":"44","author":"Kaufman","year":"2005","journal-title":"Angew. 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