Structure and surface analyses of a newly synthesized acyl thiourea derivative along with its in silico and in vitro investigations for RNR, DNA binding, urease inhibition and radical scavenging activities

N-((4-Acety[phenypcarbamothioyl)-2,4-dich[orobenzamide (4) was synthesized by the treatment of 2,4-dich[orobenzoyl chloride with potassium thiocyanate in a 1 : 1 molar ratio in dry acetone to afford the 2,4-dich[orobenzoy[ isothiocyanate in situ which on reaction with acetyl aniline furnished (4) in good yield and high purity. The compound was confirmed by FTIR, H-1-NMR, and C-13-NMR and single crystal X-ray diffraction studies. The planar rings were situated at a dihedral angle of 33.32(6)degrees. The molecules, forming S(6) ring motifs with the intramoIecuIar N-H center dot center dot center dot O hydrogen bonds, were [inked through intermolecular C-H center dot center dot center dot O and N-H center dot center dot center dot S hydrogen bonds, enclosing R-2(2) (8) ring motifs, into infinite double chains along [101]. C-H center dot center dot center dot pi and pi center dot center dot center dot pi interactions with an inter-centroid distance of 3.694 (1) A helped to consolidate a three-dimensional architecture. HirshfeEd surface (HS) analysis further indicated that the most important contributions for the crystal packing were from H center dot center dot center dot C/C center dot center dot center dot H (20.9%), H center dot center dot center dot H (20.5%), H center dot center dot center dot O/O center dot center dot center dot H (19.4%), H center dot center dot center dot O/O center dot center dot center dot H (13.8%) and H center dot center dot center dot S/S center dot center dot center dot H (8.9%) interactions. Thus C-H center dot center dot center dot pi (ring), pi center dot center dot center dot pi, van der Waa[s interactions and hydrogen bonding played the major roles in the crystal packing. The electronic structure and computed DFT (density functional theory) parameters identified the reactivity profile of compound (4). In silico binding of (4) with RNA indicated the formation of a stable protein[igand complex via hydrogen bonding, while DNA docking studies inferred (4) as a potent groove binder. The experimentally observed hypochromic change (57.2%) in the UV-visible spectrum of (4) in the presence of varying DNA concentrations together with the evaluated binding parameters (K-b; 7.9 x 10(4) M-1, Delta G; -28.42 kJ mol(-1)) indicated spontaneous interaction of (4) with DNA via groove binding and hence supported the findings obtained through docking analysis. This compound also showed excellent urease inhibition activity in both in silico and vitro studies with an IC(50 )value of 0.0389 +/- 0.0017 mu M. However, the radical scavenging efficiency of (4) was found to be modest in comparison to C.