The crystal structure of first copper(II) complex of a pyridine-2-carboxamidrazone - a potential antitumor agent

Nikhil Gokhale, Subhash Padhye, Dan Rathbone, David Billington, Phillip Lowe, Carl Schwalbe, Chris Newton

Research output: Contribution to journalArticle

Abstract

The crystal structure of the neutral, distorted square planar copper(II) complex, viz. cis-[dichloro (N'-(2-benzyloxybenzylidene) pyridine-2-carboxamidrazone) copper(II)] (1) is reported which is the first well-characterized copper(II) complex of the series (space group C2/c, a = 18.414(5) Angstrom; b = 8.6510(10) Angstrom; c = 27.091(4) Angstrom; alpha = 90 degrees; beta = 109.800(17)degrees; gamma = 90 degrees; R-1 = 0.0331 wR(2) = 0.0852). The distortion from square planar geometry is thought to arise from the non-equivalent ligand donor set. The Cu-Cl bonds are equivalent with one of the Cl atoms making intermolecular contact at 2.6070 Angstrom with adjacent copper rendering a pseudo-square pyramidal geometry around copper. The complex is further characterized by UV/VIS spectroscopy, electrochemistry and magnetic susceptibility measurements. The in vitro antitumor activity of this complex and the parent ligand is determined against the human breast cancer cell-line MCF-7 which revealed that copper complexation renders a highly antiproliferative compound with IC50 value of 3 muM.
Original languageEnglish
Pages (from-to)26-29
Number of pages4
JournalInorganic Chemistry Communications
Volume4
Issue number1
DOIs
Publication statusPublished - Jan 2001

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Antineoplastic Agents
Pyridine
Copper
pyridines
Crystal structure
copper
crystal structure
magnetic permeability
Ligands
ligands
Geometry
Electrochemistry
electrochemistry
geometry
Ultraviolet spectroscopy
Complexation
Magnetic susceptibility
cultured cells
breast
pyridine

Keywords

  • carboxamidrazone
  • copper complex
  • antitumor activity
  • breast cancer

Cite this

Gokhale, Nikhil ; Padhye, Subhash ; Rathbone, Dan ; Billington, David ; Lowe, Phillip ; Schwalbe, Carl ; Newton, Chris. / The crystal structure of first copper(II) complex of a pyridine-2-carboxamidrazone - a potential antitumor agent. In: Inorganic Chemistry Communications . 2001 ; Vol. 4, No. 1. pp. 26-29.
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The crystal structure of first copper(II) complex of a pyridine-2-carboxamidrazone - a potential antitumor agent. / Gokhale, Nikhil; Padhye, Subhash; Rathbone, Dan; Billington, David; Lowe, Phillip; Schwalbe, Carl; Newton, Chris.

In: Inorganic Chemistry Communications , Vol. 4, No. 1, 01.2001, p. 26-29.

Research output: Contribution to journalArticle

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T1 - The crystal structure of first copper(II) complex of a pyridine-2-carboxamidrazone - a potential antitumor agent

AU - Gokhale, Nikhil

AU - Padhye, Subhash

AU - Rathbone, Dan

AU - Billington, David

AU - Lowe, Phillip

AU - Schwalbe, Carl

AU - Newton, Chris

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N2 - The crystal structure of the neutral, distorted square planar copper(II) complex, viz. cis-[dichloro (N'-(2-benzyloxybenzylidene) pyridine-2-carboxamidrazone) copper(II)] (1) is reported which is the first well-characterized copper(II) complex of the series (space group C2/c, a = 18.414(5) Angstrom; b = 8.6510(10) Angstrom; c = 27.091(4) Angstrom; alpha = 90 degrees; beta = 109.800(17)degrees; gamma = 90 degrees; R-1 = 0.0331 wR(2) = 0.0852). The distortion from square planar geometry is thought to arise from the non-equivalent ligand donor set. The Cu-Cl bonds are equivalent with one of the Cl atoms making intermolecular contact at 2.6070 Angstrom with adjacent copper rendering a pseudo-square pyramidal geometry around copper. The complex is further characterized by UV/VIS spectroscopy, electrochemistry and magnetic susceptibility measurements. The in vitro antitumor activity of this complex and the parent ligand is determined against the human breast cancer cell-line MCF-7 which revealed that copper complexation renders a highly antiproliferative compound with IC50 value of 3 muM.

AB - The crystal structure of the neutral, distorted square planar copper(II) complex, viz. cis-[dichloro (N'-(2-benzyloxybenzylidene) pyridine-2-carboxamidrazone) copper(II)] (1) is reported which is the first well-characterized copper(II) complex of the series (space group C2/c, a = 18.414(5) Angstrom; b = 8.6510(10) Angstrom; c = 27.091(4) Angstrom; alpha = 90 degrees; beta = 109.800(17)degrees; gamma = 90 degrees; R-1 = 0.0331 wR(2) = 0.0852). The distortion from square planar geometry is thought to arise from the non-equivalent ligand donor set. The Cu-Cl bonds are equivalent with one of the Cl atoms making intermolecular contact at 2.6070 Angstrom with adjacent copper rendering a pseudo-square pyramidal geometry around copper. The complex is further characterized by UV/VIS spectroscopy, electrochemistry and magnetic susceptibility measurements. The in vitro antitumor activity of this complex and the parent ligand is determined against the human breast cancer cell-line MCF-7 which revealed that copper complexation renders a highly antiproliferative compound with IC50 value of 3 muM.

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