| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1307918 | Inorganica Chimica Acta | 2016 | 8 Pages |
•Change in binding mode.•In vitro cytotoxicity evaluation of complexes.•Molecular docking study.
Synthesis of Isatin-N1-methyl-thiosemicarbazone (H2itsc-N1-Me, H2L1) and isatin-N1-ethyl-thiosemicarbazone (H2itsc-N1-Et, H2L2) has been carried out and the effect of substituents (at N1 atom of isatin-3-thiosemicarbazones) on nuclearity of copper(I) halide complexes has been investigated. Reactions of copper(I) halides (X = I, Br, Cl) with H2L1 and H2L2 using Ph3P as co-ligand in 1:1:1 (M:L:PPh3) molar ratio in acetonitrile yielded complexes of stoichiometry [CuX(H2L1)(Ph3P)] (X = I, C1; Br, C2; Cl, C3) and [CuX(H2L2)(Ph3P)] (X = I, C4; Br, C5; Cl, C6) respectively. All these complexes have been characterized using analytical and spectroscopic data (IR, 1H NMR and ESI mass). The single crystal structure has been solved for H2L1 and C2. The complex C2 has distorted tetrahedral geometry around copper(I) and isatin-N1-methyl-thiosemicarbazone coordinated to metal center as neutral, bidentate, N3, S-chelating ligand. Elemental analysis suggested the presence of one acetonitrile molecule in complexes C3 and C6 and half CH3CN in complexes C2 and C4 as solvent of crystallization. MTT assay, supported by docking studies have revealed the cytotoxic nature of the compounds C1–C6.
Graphical abstractUnsubstituted isatin-3-thiosemicarbazone formed mononuclear tetrahedral complexes with copper(I) halides whereas the structure of complex C2 revealed that substituent at N1 (methyl) of isatin-3-thiosemicarbazone has changed the binding mode of ligand from terminal to N3, S- chelation of its copper(I) bromide complex.Figure optionsDownload full-size imageDownload as PowerPoint slide
