Synthesis, characterisation and biological activities of mixed ligand oxovanadium (IV) complexes derived from N,N‐diethyl‐N′‐para‐substituted‐benzoylthiourea and hydrotris(3,5‐dimethylpyrazolyl)borate

Abstract

A series of oxovanadium (IV) complexes namely, [Tp*VOL1], [Tp*VOL2], [Tp*VOL3], [Tp*VOL4] and [Tp*VOL5] (where Tp = hydrotris(3,5‐dimethylpyrazolyl)borate, HL1 = 1‐benzoyl‐3,3‐diethylthiourea, HL2 = 1‐(4‐chlorobenzoyl)‐3,3‐diethylthiourea, HL3 = 1,1‐diethyl‐3‐(4‐methoxybenzoyl)thiourea, HL4 = 1,1‐diethyl‐3‐(4‐nitrobenzoyl)thiourea, HL5 = N‐(diethylcarbamothioyl)biphenyl‐4‐carboxamide) were prepared and characterised on the basis of mass spectrometry, elemental analysis and spectroscopy techniques (IR, UV–Vis and electron paramagnetic resonance, EPR) and mass spectrometry. The crystal structure of [Tp*VOL3] was elucidated from single crystal X‐ray diffraction study and the crystals adopted a triclinic system with a P‐1 (Z = 2) space group and unit cell parameters of a = 10.4953(4), b = 11.5290(5) and c = 15.0656(7) Å. The cyclic voltammetry showed a reversible oxidation of V (IV)/V(V) at about 0.50 V (vs Fc+/Fc). The HOMO and LUMO of benzoylthiourea were established by theoretical calculation based on DFT level using B3LYP method and a double numeric plus polarisation (DNP) basis set. The in vitro tests for antimicrobial activity showed that the complexes have a moderate inhibitory effect. The complex [Tp*VOL1] exhibited cytotoxic activity against the human hepatocellular carcinoma cell line (HepG2) at the concentration of 20 mg ml−1. However, no cytotoxic activity was observed against the Chang liver cells.

Isosteric O/S exchange in carbonyl(thio)ureides: molecular interactions, structure, and bioactivity assays

“…18–20 These compounds are also used as carriers in the transport of metals via an immobilized liquid polymer membrane (PILM), 21 which is decisive for the recovery of gold from diluted solutions. Thioureas are employed as ligands for building complexes with Ru( ii ) and oxovanadium, 22,23 that function as effective catalysts for the asymmetric transfer hydrogenation of aromatic ketones to yield chiral alcohols. 24…”

Synthesis and Determination of Acid Dissociation Constants of Bis-Acyl Thiourea Derivatives

“…In addition, acyl thiourea derivatives have an important place in pharmaceutical chemistry (8,9) because they can be used as an intermediate product in the synthesis of many bioactive molecules (10,11) and show a wide range of bioactivity such as anti(mico)bacterial (12-14), antifungal (15,16), antioxidant (17), and anticancer (18) as well as enzyme inhibitory (19)(20)(21)(22)(23) properties. Since acyl thiourea compounds can easily form chelate complexes on carbonyl and thiocarbonyl groups, their Pt(II), Ni(II), Zn(II), Co(II), and other many metal complexes have been synthesized (24)(25)(26)(27)(28)(29)(30).…”