Synthesis of Adamantyl-Containing Compounds - Structure Elements of Rotaxanes and Supramolecular Polymers

Abstract

Abstract. This manuscript deals with the synthesis of various Adamantane derivatives as objects of supramolecular chemistry, in particular, supramolecular Cyclodextrine polymers (SCP) and Rotaxanes. One of the structural elements of the SCP and Rotaxanes are linear molecules modified by the end-blockers. A considerable volume of adamantyl group allows Adamantane derivatives to create locking groups in Rotaxanes, and a high affinity for β-Cyclodextrine to create supramolecular polymers.

Design, Synthesis, and Molecular Docking Study of New Tyrosyl-DNA Phosphodiesterase 1 (TDP1) Inhibitors Combining Resin Acids and Adamantane Moieties

“…The starting isocyanates and isothiocyanates were synthesized using the methods described earlier. In particular, 1-adamantyl isocyanate was obtained by the Curtius rearrangement of 1-adamantyl acyl azide formed in situ by interaction of corresponding acyl chloride with sodium azide [ 28 ]. Isomeric 2-adamantyl isocyanate was synthesized by the reaction of 2-adamantylamine hydrochloride with triphosgene in the presence of sodium hydrocarbonate, with dichloromethane used as a solvent [ 29 ].…”

Narrowing Signal Distribution by Adamantane Derivatization for Amino Acid Identification Using an α-Hemolysin Nanopore

“…To modify proteinogenic AAs with adamantane, we utilized ADIC containing an isocyanate group (−NCO) as the primary reagent. The −NCO group in isocyanates is highly unsaturated, exhibiting marked chemical reactivity to allow ADIC to effectively react with the amine group in AAs as a universal modification strategy. , The modification process as outlined in the synthetic route (Figure a) is straightforward and efficient and performed under mildly basic buffer conditions, and the crude products could be readily purified by recrystallization.…”