{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:48:14Z","timestamp":1760147294095,"version":"build-2065373602"},"reference-count":17,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2023,1,23]],"date-time":"2023-01-23T00:00:00Z","timestamp":1674432000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000002","name":"The National Institute for General Medical Sciences","doi-asserted-by":"publisher","award":["P20GM103646","R15GM143702"],"award-info":[{"award-number":["P20GM103646","R15GM143702"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molbank"],"abstract":"<jats:p>(4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol was prepared through a five-step process starting from commercially available 1-acetyladamantane. Each step proceeded in moderate-to-excellent yields and the overall yield across five steps was 28%. The compound was identified and characterized by 1H and 13C{1H} NMR, high-resolution mass spectroscopy, and elemental analysis. This compound and its derivatives have the potential to be used as precursors to the synthesis of biomimetic chelating ligands.<\/jats:p>","DOI":"10.3390\/m1566","type":"journal-article","created":{"date-parts":[[2023,1,24]],"date-time":"2023-01-24T01:59:03Z","timestamp":1674525543000},"page":"M1566","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["(4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol"],"prefix":"10.3390","volume":"2023","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5762-0644","authenticated-orcid":false,"given":"Ryan B.","family":"Gaynor","sequence":"first","affiliation":[{"name":"Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Baylee N.","family":"McIntyre","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sidney E.","family":"Creutz","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,1,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"621","DOI":"10.1146\/annurev-biochem-062917-012312","article-title":"Transition Metal Sequestration by the Host-Defense Protein Calprotectin","volume":"87","author":"Zygiel","year":"2018","journal-title":"Annu. Rev. Biochem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"792","DOI":"10.1007\/s11427-016-5088-4","article-title":"Binding of Transition Metals to S100 Proteins","volume":"59","author":"Gilston","year":"2016","journal-title":"Sci. China Life Sci."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"8840","DOI":"10.1074\/jbc.M109.053934","article-title":"Distal Histidine Stabilizes Bound O2 and Acts as a Gate for Ligand Entry in Both Subunits of Adult Human Hemoglobin*","volume":"285","author":"Birukou","year":"2010","journal-title":"J. Biol. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1146\/annurev-biochem-013118-111529","article-title":"Soluble Methane Monooxygenase","volume":"88","author":"Banerjee","year":"2019","journal-title":"Annu. Rev. Biochem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"5107","DOI":"10.1021\/ic025855m","article-title":"Stability and Acidity Constants for Ternary Ligand-Zinc-Hydroxo Complexes of Tetradentate Tripodal Ligands","volume":"42","author":"Chiu","year":"2003","journal-title":"Inorg. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5222","DOI":"10.1021\/ja00330a031","article-title":"Tris(Imidazole)-Containing Phosphine: M2+ Complexes as Biomimetic Catalysts. Importance of a L:M2+-OH\u2212 in the Catalyzed Bimolecular Hydrolysis of p-Nitrophenyl Picolinate","volume":"106","author":"Brown","year":"1984","journal-title":"J. Am. Chem. Soc."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1712","DOI":"10.1039\/C39870001712","article-title":"A New Cyclam with an Appended Imidazole. The First Biomimetic Ligation of Imidazole for Axial \u03c0-Interaction with Metal Ions","volume":"22","author":"Kimura","year":"1987","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3945","DOI":"10.1002\/ejic.200300228","article-title":"A Novel Water-Soluble Tripodal Imidazolyl Ligand as a Model for the Tris(Histidine) Motif of Zinc Enzymes: Nickel, Cobalt and Zinc Complexes and a Comparison with Metal Binding in Carbonic Anhydrase","volume":"2003","author":"Kunz","year":"2003","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"4707","DOI":"10.1016\/j.tetlet.2006.04.119","article-title":"Directed Regioselectivity of Bromination of Ketones with NBS: Solvent-Free Conditions versus Water","volume":"47","author":"Pravst","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"18827","DOI":"10.3390\/molecules201018827","article-title":"Synthesis and Crystallographic Insight into the Structural Aspects of Some Novel Adamantane-Based Ester Derivatives","volume":"20","author":"Kumar","year":"2015","journal-title":"Molecules"},{"key":"ref_11","first-page":"2292","article-title":"Synthesis and Properties of Dioximes of the Adamantane Series","volume":"22","author":"Moiseev","year":"1986","journal-title":"Zhurnal Org. Khimii"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"24","DOI":"10.15227\/orgsyn.055.0024","article-title":"1-bromo-3-methyl-2-butanone","volume":"55","author":"Marquet","year":"1976","journal-title":"Org. Synth."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1589","DOI":"10.1021\/jo00085a056","article-title":"A Regiospecific Synthesis of 1,4-Disubstituted Imidazoles","volume":"59","author":"Sorrell","year":"1994","journal-title":"J. Org. Chem."},{"key":"ref_14","unstructured":"Darensbourg, M.Y. (2007). Inorganic Syntheses, John Wiley & Sons, Inc."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"10416","DOI":"10.1039\/c1dt10588d","article-title":"Origins of Stereoselectivity in Optically Pure Phenylethaniminopyridinetris-Chelates M(NN\u2032)3n+ (M = Mn, Fe, Co, Ni and Zn)","volume":"40","author":"Howson","year":"2011","journal-title":"Dalton Trans."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2379","DOI":"10.1016\/j.bmc.2013.01.063","article-title":"Cytotoxic Effect of (1-Methyl-1H-Imidazol-2-Yl)-Methanamine and Its Derivatives in PtII Complexes on Human Carcinoma Cell Lines: A Comparative Study with Cisplatin","volume":"21","author":"Ferri","year":"2013","journal-title":"Bioorg. Med. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1016\/j.bmc.2004.10.021","article-title":"Orally Active CCR5 Antagonists as Anti-HIV-1 Agents. Part 3: Synthesis and Biological Activities of 1-Benzazepine Derivatives Containing a Sulfoxide Moiety","volume":"13","author":"Seto","year":"2005","journal-title":"Bioorg. Med. Chem."}],"container-title":["Molbank"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-8599\/2023\/1\/M1566\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:14:10Z","timestamp":1760120050000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-8599\/2023\/1\/M1566"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1,23]]},"references-count":17,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2023,3]]}},"alternative-id":["M1566"],"URL":"https:\/\/doi.org\/10.3390\/m1566","relation":{},"ISSN":["1422-8599"],"issn-type":[{"type":"electronic","value":"1422-8599"}],"subject":[],"published":{"date-parts":[[2023,1,23]]}}}