Synthesis, Spectroscopic Characterization, Calculational Studies and in Vitro Antitumoral Activity 4-(3-(1H-imidazol-1-yl)propyl)-(thiophen-2-ylmethyl)-1H-1,2,4-triazol-5(4H)-one

Abstract

4-(3-(1H-imidazol-1-yl)propyl)-(thiophen-2-ylmethyl)-1H-1,2,4-triazol-5(4H) -one (IPTT), C<inf>13</inf>H<inf>15</inf>N<inf>5</inf>OS, was synthesized and characterized by 13C NMR, 1H NMR, IR and single-crystal X-ray diffraction. The structure of IPTT is stabilized by three intermolecular hydrogen bonds and by intermolecular CH⋯π interaction. The compound IPTT was modelled by using DFT method. Calculations of vibrational frequencies, gauge including atomic orbital (GIAO), 1H and 13C NMR chemical shifts of IPTT in the ground state, total electronic charge density map and frontier molecular orbitals were performed at B3LYP/6-31 G(d) level of theory were carried out by using DFT method with 6-31 G(d) basis set. The structural parameters obtained by geometry optimization, the theoretical vibrational frequencies and chemical shift values are in good agreement with experimental ones. FT-IR, NMR and X-ray analytical results of IPTT show that the compound exists as keto form, that was supported by DFT calculations. In addition, in vitro studies showed hopeful antitumoral activity of the title IPTT compound. © 2011 Elsevier B.V. All rights reserved.