Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2023 Mar;2023(1):M1566.
doi: 10.3390/M1566. Epub 2023 Jan 23.

(4-(Adamantan-1-yl)-1-(isopropyl)-1 H-imidazol-2-yl)methanol

Ryan B Gaynor  1 , Baylee N McIntyre  1 , Sidney E Creutz  1
Affiliations

(4-(Adamantan-1-yl)-1-(isopropyl)-1 H-imidazol-2-yl)methanol

Ryan B Gaynor et al. Molbank. 2023 Mar.

Abstract

(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.

Keywords: bioinspired; imidazoles; ligand precursors.

PubMed Disclaimer

Conflict of interest statement

Conflicts of Interest: The authors declare no conflict of interest.

Figures

Scheme 1.
Scheme 1.
Preparation of compound 5. DMF = dimethylformamide; THF = tetrahydrofuran.
See this image and copyright information in PMC

References

    1. Zygiel EM; Nolan EM Transition Metal Sequestration by the Host-Defense Protein Calprotectin. Annu. Rev. Biochem 2018, 87, 621–643. - PMC - PubMed
    1. Gilston BA; Skaar EP; Chazin WJ Binding of Transition Metals to S100 Proteins. Sci. China Life Sci 2016, 59, 792–801. - PMC - PubMed
    1. Birukou I; Schweers RL; Olson JS Distal Histidine Stabilizes Bound O2 and Acts as a Gate for Ligand Entry in Both Subunits of Adult Human Hemoglobin*. J. Biol. Chem 2010, 285, 8840–8854. - PMC - PubMed
    1. Banerjee R; Jones JC; Lipscomb JD Soluble Methane Monooxygenase. Annu. Rev. Biochem 2019, 88, 409–431. - PubMed
    1. Chiu Y-H; Canary JW Stability and Acidity Constants for Ternary Ligand-Zinc-Hydroxo Complexes of Tetradentate Tripodal Ligands. Inorg. Chem 2003, 42, 5107–5116. - PubMed

LinkOut - more resources