{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,28]],"date-time":"2026-01-28T03:30:21Z","timestamp":1769571021639,"version":"3.49.0"},"reference-count":48,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2026,1,27]],"date-time":"2026-01-27T00:00:00Z","timestamp":1769472000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Research funding for this project was provided by the Committee of Science of the Ministry of Science and Higher Education of the Republic of Kazakhstan","award":["AP26198287"],"award-info":[{"award-number":["AP26198287"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The cyclic adamantane framework possesses unique properties such as bulkiness, symmetry, and high lipophilicity. Research aimed at discovering new pharmaceutical agents within the adamantane series continues. In the present work, a targeted modification was carried out to combine two pharmacophore fragments\u2014adamantane and piperidine\u2014within a single molecule. Based on a series of N-substituted piperidin-4-ones, the corresponding secondary alcohols were obtained by reduction with sodium borohydride in isopropanol and subsequent acylation of these alcohols with adamantane carbonyl chloride yielded the corresponding adamantane-carboxylate esters. The structure of the synthesized compounds was studied by NMR methods, including COSY (1H-1H), HMQC (1H-13C) and HMBC (1H-13C) techniques. The values of chemical shifts, multiplicities, and integrated intensities of 1H and 13C signals in one-dimensional NMR spectra were determined. The results of COSY (1H-1H), HMQC (1H-13C), and HMBC (1H-13C) revealed homo- and heteronuclear interactions, confirming the structure of the studied compounds. The cytotoxic activities of the synthesized compounds were studied. It was found that the synthesized substituted piperidines bearing an adamantane fragment exhibit in vitro antimicrobial and antifungal activity against museum microbial strains (Escherichia coli ATCC 8739, Staphylococcus aureus ATCC 6538-P, Candida albicans ATCC 10231, Cryptococcus neoformans) and demonstrate significant advantages over the reference drugs used in clinical practice, such as fluconazole and ampicillin. These compounds are therefore recommended for further in-depth studies.<\/jats:p>","DOI":"10.3390\/molecules31030439","type":"journal-article","created":{"date-parts":[[2026,1,27]],"date-time":"2026-01-27T15:41:56Z","timestamp":1769528516000},"page":"439","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis, Antimicrobial Activity and Cytotoxicity of Novel (Piperidin-4-yl)adamantane-1-carboxylate N-Substituted Derivatives"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0381-7481","authenticated-orcid":false,"given":"Kaldybay D.","family":"Praliyev","sequence":"first","affiliation":[{"name":"Laboratory of Synthetic and Natural Medicinal Compounds Chemistry, A.B. Bekturov Institute of Chemical Sciences JSC, 106 Sh. Ualikhanov St., Almaty 050010, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9074-1464","authenticated-orcid":false,"given":"Gulmira S.","family":"Akhmetova","sequence":"additional","affiliation":[{"name":"Laboratory of Synthetic and Natural Medicinal Compounds Chemistry, A.B. Bekturov Institute of Chemical Sciences JSC, 106 Sh. Ualikhanov St., Almaty 050010, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6976-6096","authenticated-orcid":false,"given":"Ulzhalgas B.","family":"Issayeva","sequence":"additional","affiliation":[{"name":"Laboratory of Synthetic and Natural Medicinal Compounds Chemistry, A.B. Bekturov Institute of Chemical Sciences JSC, 106 Sh. Ualikhanov St., Almaty 050010, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3807-1299","authenticated-orcid":false,"given":"Samir A.","family":"Ross","sequence":"additional","affiliation":[{"name":"National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, Oxford, MS 38677, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2665-178X","authenticated-orcid":false,"given":"Manas T.","family":"Omyrzakov","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Asfendiyarov Kazakh National Medical University, Almaty 050000, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0397-7840","authenticated-orcid":false,"given":"Ilya S.","family":"Korotetskiy","sequence":"additional","affiliation":[{"name":"Scientific Center for Anti-Infectious Drugs JSC, Almaty 050060, Kazakhstan"},{"name":"Department Biochemical Engineering, LLC International Engineering and Technological University, Almaty 050060, Kazakhstan"},{"name":"LLP Research and Production Association Kazpharmacom, Irgeli 040900, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8610-7321","authenticated-orcid":false,"given":"Ardak B.","family":"Jumagaziyeva","sequence":"additional","affiliation":[{"name":"Scientific Center for Anti-Infectious Drugs JSC, Almaty 050060, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9996-9476","authenticated-orcid":false,"given":"Aigul E.","family":"Malmakova","sequence":"additional","affiliation":[{"name":"Laboratory of Synthetic and Natural Medicinal Compounds Chemistry, A.B. Bekturov Institute of Chemical Sciences JSC, 106 Sh. Ualikhanov St., Almaty 050010, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0079-4755","authenticated-orcid":false,"given":"Tulegen M.","family":"Seilkhanov","sequence":"additional","affiliation":[{"name":"The Laboratory of Engineering Profile of NMR Spectroscopy, Sh. Ualikhanov Kokshetau State University, Kokshetau 020000, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2322-220X","authenticated-orcid":false,"given":"Ubaidilla M.","family":"Datkhayev","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Asfendiyarov Kazakh National Medical University, Almaty 050000, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7194-0556","authenticated-orcid":false,"given":"Lyudmila N.","family":"Ivanova","sequence":"additional","affiliation":[{"name":"Scientific Center for Anti-Infectious Drugs JSC, Almaty 050060, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7428-0074","authenticated-orcid":false,"given":"Zhanar A.","family":"Iskakbayeva","sequence":"additional","affiliation":[{"name":"Scientific Center for Anti-Infectious Drugs JSC, Almaty 050060, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2322-8863","authenticated-orcid":false,"given":"Olzhas T.","family":"Seilkhanov","sequence":"additional","affiliation":[{"name":"The Laboratory of Engineering Profile of NMR Spectroscopy, Sh. Ualikhanov Kokshetau State University, Kokshetau 020000, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6436-803X","authenticated-orcid":false,"given":"Natalya V.","family":"Zubenko","sequence":"additional","affiliation":[{"name":"Scientific Center for Anti-Infectious Drugs JSC, Almaty 050060, Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2026,1,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3245","DOI":"10.2174\/0929867323666160525114026","article-title":"A\u0434\u0430\u043c\u0430\u043d\u0442\u0430\u043d\u2014Adamantane is a leading drug structure in clinical practice","volume":"23","author":"Spilovska","year":"2016","journal-title":"Curr. Med. 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