Structural conversion of an oxazolidine ligand upon treatment with copper(I) and (II) halides; structural, spectral, theoretical and docking studies

In this work, the 2-(2-(pyridin-2-yl)oxazolidin-3-yl)ethanol (AEPC) ligand was prepared under solvent free conditions using ultrasonic irradiation, before reaction with a Cu(NO3)2/KSCN mixture, CuCl2 and CuI, the products of which were characterized by elemental analysis, UV-Vis, FT-IR spectroscopy and single-crystal X-ray diffraction. The X-ray analyses results revealed that AEPC, after reactions with the three copper(I/II) halides, gave structures ([Cu(DEA)Cl2] (2), DEA = diethanolamine, [Cu(BHEG)2] (3), BHEG = bis(2-hydroxyethyl)glycinato), however it retains its structure on treatment with Cu(NO3)2/KSCN mixture ([Cu(AEPC)(NCS)2] (1)). The geometrical parameters for the complexes were compared with the Cambridge Structural Database (CSD) and coordination modes for thiocyanate ion were extracted. In the crystal structure of 1, the copper ion has a distorted square-pyramidal geometry and a CuNpyN2NCSNtertOalc environment in which the AEPC acts as NN'O-donor in a facial coordination mode. In the crystal structure of 2, the copper ion has a Cu(Nsec)(Oalc)2Cl2 environment and distorted square-pyramidal geometry in which the DEA ligand is coordinated as a mer-NO2-donor. The copper ion in 3 has a CuN2O4 environment and distorted octahedral geometry. The ability of these compounds to interact with the nine biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS and Top II) was investigated by Docking calculations and compared with that of doxorubicin. The thermodynamic stability of 1 and its isomer and also charge distribution patterns were studied by DFT and NBO analysis, respectively