Synthesis, crystal structure and Hirshfeld surface analysis of 1-acetyl-5-(2-methylpropyl)-2-thioxo-imidazolidin-4-one

Abstract

The hydantoin and thiohydantoin heterocycles are present in a wide range of biologically active compounds including therapeutic drugs for the treatment of seizures and anti-tumor compounds. Thiohydantoins, have also been used as anti-convulsant agents and are present in fungicides, herbicides and natural products. However, the principal current interest comes from the application of thiohydantoins for the treatment of prostate cancers. Structural characterization of hydantoin and thiohydantoin are important to comprehend their effect mechanisms because of their considerable biological effects. In this work a thiohydantoin derivative, 1-acetyl-5-(2-methylpropyl)-2-thioxo-imidazolidin-4-one (I), has been obtained by the reaction of 2-amino-4-methylpentanoic acid with KSCN in acetic anhydride-acetic acid mixture. The heterocyclic compound was characterized by FTIR, NMR, powder and single-crystal X-ray diffraction analysis. This compound crystallizes in the triclinic system, space group P-1 (Nº2), Z=4, with two independent molecules in the unit asymmetric. The thiohydantoin (I) forms one-dimensional hydrogen bonded chains, via a single hydrogen bond between the carbonyl oxygens and the amine ring N3 position, that run along [100] direction, with graphset motif C(6). The nature of intermolecular interactions has been analyzed through Hirshfeld surfaces and 2D fingerprint plots.