N-(naphthyl)-N′-(methoxy carbonyl)thiocarbamide and its Cu(I) complex: synthesis, spectroscopic, X-ray, DFT and in vitro cytotoxicity study

Abstract

The structural characterization of two new compounds N-naphthyl-N′-methoxycarbonyl thiocarbamide (NMCT) (1) and its Cu(I) complex, bis(N-naphthyl-N′-methoxycarbonyl thiocarbamide) copper(I) chloride [(NMCT)₂CuCl] (1a) have been done by spectroscopic techniques (FT-IR, ¹H NMR, ¹³C NMR and electronic spectroscopy) and X-ray crystallography. To get a deeper insight of vibrational frequencies and electronic transitions, DFT and TD-DFT studies have also been performed. X-ray study revealed trigonal planar geometry around copper(I). The ligand coordinates through thione sulfur only. The cytotoxicity of 1 and 1a has been assayed in five human carcinoma cell lines, 2008, C13* (cervical carcinoma), A2780, A2780/CP and IGROV-1 (ovarian carcinoma). Both the compounds exhibited cytotoxicity. The inhibitory activity of copper complex was better than ligand against all the cell lines.

Graphical Abstract

Keywords:

• N-Naphthyl-N′-methoxycarbonyl thiocarbamide
• Spectral techniques
• X-ray crystallography
• Trigonal planar geometry
• DFT study
• Cytotoxicity

Acknowledgements

The author, DPS, is grateful to Banaras Hindu University, Varanasi, India for the financial assistance and research scholarship. RJB acknowledges the NSF–MRI program [grant number CHE0619278] for funds to purchase the X-ray diffractometer.