Facile synthesis, DNA binding, Urease inhibition, anti-oxidant, molecular docking and DFT studies of 3-(3-Bromo-phenyl)-1-(2-trifluoromethyl-phenyl)-propenone and 3-(3-Bromo-5 chloro-phenyl)-1-(2-trifluoromethyl-phenyl)-propenone

Abstract Two new chalcones namely 3-(3-Bromo-phenyl)-1-(2-trifluoromethyl-phenyl)-propenone (1) and 3-(3-Bromo-5-chloro-phenyl)-1-(2-trifluoromethyl-phenyl)-propenone (2) were synthesized from substituted aldehydes and fluorinated acetophenone through base catalyzed condensation reaction. The structural confirmation of synthesized compounds was furnished by different spectroscopic techniques i.e., (1H NMR, FT-IR, mass spectrometry and UV–visible analysis). The interaction of 1 and 2 with Salmon sperm DNA (SS-DNA) was studied using UV–visible spectroscopy. The Urease inhibition and antioxidant potential were also evaluated experimentally which were further supported by molecular docking studies. To investigate drug discovery endeavors of our synthesized compounds ADME properties were explored. The calculations of frontier molecular orbitals (FMOs), natural population analysis (NPA), natural bond orbitals (NBOs) and nonlinear optical (NLO) analysis of 1 and 2 were performed at B3LYP/6-311 G(d,p) level of DFT. Time dependent density functional theory (TD-DFT) was used to describe photo-physical properties of synthesized compounds. Additionally, natural population analysis (NPA) and NBO were used to explore inter and intra molecular interactions as well as hyper conjugative interactions. The experimental results revealed that the compounds 1 and 2 interact strongly with SS-DNA through intercalation mode. UV/Vis spectrum obtained from DFT calculations correlates very well with the experimentally obtained spectrum. Furthermore, DFT studies showed that hyper conjugative interactions lead to higher stabilization of 2 than 1.