Synthesis of Functionalized Adamantane Derivatives: (3 + 1)-Scaffolds for Applications in Medicinal and Material Chemistry

Fleck, C.; Franzmann, Elisa; Claes, Dorith; Rickert, Aljona; Maison, Wolfgang

doi:10.1055/s-0033-1338470

Cited by 22 publications

(2 citation statements)

References 43 publications

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“…A common synthetic precursor for the synthesis of suitable tripodal catecholates is the AB 3 -scaffold 1 [40–42] (Scheme 1) which is readily available in a few steps from adamantane as a cheap starting material [43]. Amine 1 was coupled to a commercially available PEG-carboxylate (5 kDa) with EDC/DMAP.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

Klitsche¹,

Ramcke²,

Migenda³

et al. 2015

Beilstein J. Org. Chem.

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SummaryA common approach to generate tailored materials and nanoparticles (NPs) is the formation of molecular monolayers by chemisorption of bifunctional anchor molecules. This approach depends critically on the choice of a suitable anchor group. Recently, bifunctional catecholates, inspired by mussel-adhesive proteins (MAPs) and bacterial siderophores, have received considerable interest as anchor groups for biomedically relevant metal surfaces and nanoparticles. We report here the synthesis of new tripodal catecholates as multivalent anchor molecules for immobilization on metal surfaces and nanoparticles. The tripodal catecholates have been conjugated to various effector molecules such as PEG, a sulfobetaine and an adamantyl group. The potential of these conjugates has been demonstrated with the immobilization of tripodal catecholates on ZnO NPs. The results confirmed a high loading of tripodal PEG-catecholates on the particles and the formation of stable PEG layers in aqueous solution.

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Section: Resultsmentioning

confidence: 99%

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

Klitsche¹,

Ramcke²,

Migenda³

et al. 2015

Beilstein J. Org. Chem.

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“…The molecule can be modified by the C-H bond activation for the direct nucleophilic substitution or radical reactions [8][9][10][11][12]. It can be also modified by the introduction of substituents or heterocyclic atoms for designing new derivatives [13,14].…”

Section: Introductionmentioning

confidence: 99%

In vitro and in vivo investigations on anti-influenza effect of adamantyl (alkyl, cycloalkyl) derivatives of aminopropanol-2

et al. 2018

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To establish anti-influenza activities for 8 compounds of adamantyl (alkyl, cycloalkyl) derivatives of aminopropanol-2 in vitro and in vivo investigations. Methods. The antiviral action of compounds was determined in vitro by reduction of infectious titer of the influenza virus in the Madin-Darby Canine Kidney (MDCK) cell culture and in vivo on the model of influenza pneumonia in mice. Results. Three of eight studied compounds inhibit the reproduction of the influenza virus strain A/FM/1/47(H1N1) by more than 2 lg ID 50 in the concentration range from < 0.39 µg/ml (the compounds 30 and 33) to 1.56 µg/ml (the compound 5), their chemotherapeutic indices are 256 and 16, respectively. The experiments in vivo showed that in prophylactic scheme the efficiency index (EI) of the compounds 5 and 30 is 60 %; in therapeutic scheme EI of the compounds 5 and 33 is 100 % that is two times higher, than for rimantadine. Conclusions. High chemotherapeutic indices of the compounds 30, 33 and their ability to suppress the influenza virus reproduction in the MDCK cell culture by more than 2 lg ID 50 indicate the anti-influenza activity of these compounds. It has been also confirmed by in vivo experiment. K e y w o r d s: influenza virus, adamantyl (alkyl, cycloalkyl) derivatives of aminopropanol-2, antiviral activity.

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A Comprehensive Review on Selective Catalytic Methods for Functionalization of Adamantane Scaffolds

Kumar,

Annie,

Solanke

et al. 2024

Asian J Org Chem

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Over the decades, conventional techniques have been reported for the direct conversion of a substantial framework of adamantyl C(sp3)‐H/Br/COOH bonds to various C‐C, C‐N, and other C‐X bonds enabled by various catalytic conditions and reagents. There are various simple and direct methods for converting adamantane tertiary and secondary C‐(Sp3)–H/X/M bonds to quaternary/ tertiary carbon–carbon bonds that have been reported in previous years, which include methods such as catalytic approaches, cross‐coupling reactions, C‐H bond functionalization, radical reactions, organometallics, and dual catalysis, etc. The selective catalytic techniques published between 2010 and 2023 are covered in this article. These adamantane derivatives are broadly studied in various fields such as medicinal chemistry applications, drug development, supramolecular chemistry, material science, catalysts/ligands and nanotechnologies.

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Synthesis of Functionalized Adamantane Derivatives: (3 + 1)-Scaffolds for Applications in Medicinal and Material Chemistry

Cited by 22 publications

References 43 publications

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

In vitro and in vivo investigations on anti-influenza effect of adamantyl (alkyl, cycloalkyl) derivatives of aminopropanol-2

A Comprehensive Review on Selective Catalytic Methods for Functionalization of Adamantane Scaffolds

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