{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T19:15:40Z","timestamp":1790536540276,"version":"4.1.0"},"reference-count":74,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2021,10,21]],"date-time":"2021-10-21T00:00:00Z","timestamp":1634774400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Curcumin (CUR) is a natural compound that exhibits anti-inflammatory, anti-bacterial, and other biological properties. However, its application as an effective drug is problematic due to its poor oral bioavailability, solubility in water, and poor absorption from the gastrointestinal tract. The aim of this work is to synthesize monocarbonyl analogs of CUR based on the 9-methyl-9-azabicyclo[3.2.1]nonan-3-one (pseudopelletierine, granatanone) scaffold to improve its bioavailability. Granatane is a homologue of tropane, whose structure is present in numerous naturally occurring alkaloids, e.g., l-cocaine and l-scopolamine. In this study, ten new pseudopelletierine-derived monocarbonyl analogs of CUR were successfully synthesized and characterized by spectral methods and X-ray crystallography. Additionally, in vitro test of the cytotoxicity and anti-inflammatory properties of the synthesized compounds were performed.<\/jats:p>","DOI":"10.3390\/ijms222111384","type":"journal-article","created":{"date-parts":[[2021,10,22]],"date-time":"2021-10-22T00:22:02Z","timestamp":1634862122000},"page":"11384","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity"],"prefix":"10.3390","volume":"22","author":[{"given":"Damian","family":"Pawelski","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Pharmacy with the Division of Laboratory Medicine, Medical University of Bialystok, Mickiewicza 2A, 15-222 Bialystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alicja","family":"Walewska","sequence":"additional","affiliation":[{"name":"Department of Regenerative Medicine and Immune Regulation, Medical University of Bialystok, Waszyngtona 13, 15-269 Bialystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7356-235X","authenticated-orcid":false,"given":"Sylwia","family":"Ksiezak","sequence":"additional","affiliation":[{"name":"Department of Regenerative Medicine and Immune Regulation, Medical University of Bialystok, Waszyngtona 13, 15-269 Bialystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dariusz","family":"Sredzinski","sequence":"additional","affiliation":[{"name":"Regional Blood Donation and Blood Treatment Center in Bialystok, M. Sklodowskiej-Curie 23, 15-950 Bialystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8917-5621","authenticated-orcid":false,"given":"Piotr","family":"Radziwon","sequence":"additional","affiliation":[{"name":"Regional Blood Donation and Blood Treatment Center in Bialystok, M. Sklodowskiej-Curie 23, 15-950 Bialystok, Poland"},{"name":"Department of Hematology, Medical University of Bialystok, M. Sklodowskiej-Curie 24A, 15-276 Bialystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marcin","family":"Moniuszko","sequence":"additional","affiliation":[{"name":"Department of Regenerative Medicine and Immune Regulation, Medical University of Bialystok, Waszyngtona 13, 15-269 Bialystok, Poland"},{"name":"Department of Allergology and Internal Medicine, Medical University of Bialystok, M. Sklodowskiej-Curie 24A, 15-276 Bialystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ramesh","family":"Gandusekar","sequence":"additional","affiliation":[{"name":"Department of Regenerative Medicine and Immune Regulation, Medical University of Bialystok, Waszyngtona 13, 15-269 Bialystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8980-1474","authenticated-orcid":false,"given":"Andrzej","family":"Eljaszewicz","sequence":"additional","affiliation":[{"name":"Department of Regenerative Medicine and Immune Regulation, Medical University of Bialystok, Waszyngtona 13, 15-269 Bialystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2358-0960","authenticated-orcid":false,"given":"Ryszard","family":"Lazny","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Bialystok, Ciolkowskiego 1K, 15-245 Bialystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9339-7745","authenticated-orcid":false,"given":"Krzysztof","family":"Brzezinski","sequence":"additional","affiliation":[{"name":"Department of Structural Biology of Prokaryotic Organisms, Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12\/14, 61-074 Poznan, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0538-6059","authenticated-orcid":false,"given":"Marta E.","family":"Plonska-Brzezinska","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Pharmacy with the Division of Laboratory Medicine, Medical University of Bialystok, Mickiewicza 2A, 15-222 Bialystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,10,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1181","DOI":"10.3389\/fphar.2018.01181","article-title":"Curcumin\u2019s Metabolites, Tetrahydrocurcumin and Octahydrocurcumin, Possess Superior Anti-Inflammatory Effects in Vivo Through Suppression of TAK1-NF-\u039aB Pathway","volume":"9","author":"Zhang","year":"2018","journal-title":"Front. 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