Synthesis, crystal structure, antiproliferative activity, DNA binding and density functional theory calculations of 3‐(pyridin‐2‐yl)‐8‐tert‐butylcoumarin and its copper(II) complex

Abstract

A Cu(II)–coumarin complex, [CuL2(NO3)2] (2), where L = 3‐(pyridin‐2‐yl)‐8‐tert‐butylcoumarin (1), was synthesized with Cu(NO3)2⋅3H2O and characterized using elemental, infrared and single‐crystal X‐ray diffraction analyses. The crystal structure of 1 shows that all the pyrone, benzene and pyridine rings are completely coplanar. The crystal structure of 2 is stabilized by intermolecular C–H···O and C–H···N hydrogen bonds and C···C short contacts, which lead to the formation of a two‐dimensional network structure. Density functional theory results give support to the experimentally determined monomeric structure. The in vitro cytotoxic activities of 1 and 2 were investigated against HeLa (cervical carcinoma), A549 (lung), HepG2 (liver) and HUVEC (umbilical vein) cells by MTT assay. The IC50 values show that both 1 and 2 have lower toxicity than doxorubicin and cisplatin in every case. Ligand 1 exhibits higher anti‐HeLa activity than doxorubicin. Complex 2 displays higher anti‐HeLa activity than coumarin but lower than that of cisplatin. Various spectroscopic approaches indicate that 1 and 2 could effectively bind with DNA through intercalation mode.

Coumarin-Palladium(II) Complex Acts as a Potent and Non-Toxic Anticancer Agent against Pancreatic Carcinoma Cells

“…Ulukaya and co-workers presented results of very potent anticancer activity of tested palladium(II) complex against breast carcinoma cells with IC 50 values of 0.09 μM for MDA-MB-231 and 3.05 μM for MCF-7 cells [ 26 ]. The literature data reveals many coumarin-metal based complexes with antitumor activity, [ 28 , 29 , 30 ], however, this is the first report on coumarin palladium(II) complex anticancer activity against pancreatic adenocarcinoma cells.…”

A Mini-Review: Recent Advances in Coumarin-Metal Complexes With Biological Properties

“…It is noteworthy that such chemical species as copper and cobalt are also valuable for the development of antitumor compounds. In 2020, Lu W. et al disclosed the synthesis of novel coumarin-metal complexes which may be useful in the treatment of cervical cancer ( Lu et al, 2020 ). The reaction of 8-( tert -butyl)-3-(pyridin-2-yl)-2 H -chromen-2-one with copper (II) nitrate trihydrate furnished the octahedral copper (II) complex 6 ( Table 1 ) under mild reaction conditions, whose structure was unequivocally confirmed by a single-crystal X-ray diffraction analysis.…”