Synthesis, spectroscopic characterization, calculational studies and in vitro antitumoral activity of 4-(3-(1H-imidazol-1-yl)propyl)-(thiophen-2-ylmethyl)-1H-1,2,4-triazol-5(4H)-one

✍ Scribed by Nevin Süleymanoğlu; Reşat Ustabaş; Yelda Bingöl Alpaslan; Yasemin Ünver; Mustafa Turan; Kemal Sancak

• Publisher: Elsevier Science
• Year: 2011
• Tongue: English
• Weight: 877 KB
• Volume: 989
• Category: Article
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2011.01.011

✦ Synopsis

a b s t r a c t 4-(3-(1H-imidazol-1-yl)propyl)-(thiophen-2-ylmethyl)-1H-1,2,4-triazol-5(4H)-one (IPTT), C 13 H 15 N 5 OS, was synthesized and characterized by 13 C NMR, 1 H NMR, IR and single-crystal X-ray diffraction. The structure of IPTT is stabilized by three intermolecular hydrogen bonds and by intermolecular CAHÁ Á Áp interaction. The compound IPTT was modelled by using DFT method. Calculations of vibrational frequencies, gauge including atomic orbital (GIAO), 1 H and 13 C 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.