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Published on 06/04/2021
Adamantane is composed of three fused cyclohexane rings leading to a rigid but stress-free arrangement of the carbon atoms, thus representing the most stable isomer of C10H16. Its name is derived from the Greec word adamantinos meaning diamond, as the spatial organization of the carbon atoms is for both the same.
Adamantyl-based compounds are reported for clinical use as anti-viral agents and for the treatment of medical conditions such as type 2 diabetes and neurological disorders. In most cases, the incorporation of an adamantyl moiety to a parent drug leads to improved pharmacological properties and enhanced activity. Its steric bulk alters or even restricts intramolecular reactivity and blocks the access of hydrolytic enzymes, usually leading to increased stability and prolonged plasma half-life of adamantyl-substituted compounds compared to their des-adamantyl analogues. Due to its lipophililcity, the incorporation of an adamantyl moiety typically increases the membrane solubility of a highly water-soluble compound. This fact is proven for the AIDS drug azidothymidine. The addition of an adamantyl-1-acetic acid via an ester bond led to a prodrug with improved transport across the blood brain barrier.
In other cases, adamantyl is placed instead of a phenyl ring. One example is the synthesis of adamantyl analogues of paracetamol. Concerning the substitution pattern, the ortho, meta, and para positions of the phenyl ring conform to a 1,2, 1,3 and 1,4-substution on the adamantyl ring. This is in agreement with the greater potency of the 1,4-adamanyl paracetamol derivative, which corresponds to the para-substitution in paracetamol, compared to the 1,3-derivative.
Chemical structure of the parent drug paracetamol and its adamantyl-substituted derivatives.
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Enantioselective synthesis of adamantylalanine and carboranylalanine and their incorporation into the proteasome inhibitor bortezomib; G. de Bruin, E. D. Mock, S. Hoogendoorn, A. M. C. H. van den Nieuwendijk, J. Mazurek, G. A. van der Marel, B. I. Florea, H. S. Overkleeft; Chem. Commun. 2016; 52: 4064-4067. https://doi.org/10.1039/C6CC01156J.
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