Synthesis of Novel Adamantly-containing Thiazolidinones

Diamondoids are cage hydrocarbon molecules that can be described as fully hydrogen-terminated nanometer-sized diamonds. Adamantane is the smallest diamondoids.1 The adamantyl group is present in seven compounds in current clinical use for the treatment of neurodegenerative disorders, viral infections and type 2 diabetes, and in many more substances that are in development as potential therapeutics. In many cases the adamantane motif, as a liphophile group, has been found to improve pharmacological properties of a parent compound, without increasing its toxicity.2Thiazolidinone is a five‐membered heterocyclic ring with a broad spectrum of biological activities. This is a core structure in various synthetic pharmaceuticals.3 In this work, novel adamantly containing thiazolidinones were synthesized in two steps. Firstly adamantly-contaning 1,3-disubstituted thioureas 1 were synthesized by the reaction of 1-aminoadamantane hydrochloride with phenyl isothiocyanate derivatives. Then reaction of thiourea derivatives 1 with dimethyl acetylenedicarboxylate (DMAD) 2 afford thiazolidinone derivatives 3 (Fig. 1).

کلیدواژه ها:

Adamantane motif ، Diamondoid ، Thiazolidinone