Synthesis, structure and catalytic promiscuity of a napthyl-pyrazole Mn(II) complex and structure-activity relationships

abstract

The napthyl/pyridine-pyrazole-derived complexes, [Mn(L-1)Cl-2] (1), [Co(L-1)Cl-2] (2), [Cu(mu-Cl)(Cl)(L)](2) (3), [Cu-2(L)(2)(N-3)(3)(mu 2-N-3)] (4), and [Co(L-2)Cl-2] (5) (where L-1 = bis-(3,5-dimethyl-pyrazol-1-ylmethyl)-napthalen-1-ylmethyl-amine (L-1), L = 5-methyl-pyrazol-1-ylmethyl) -napthalen-1-ylmethyl-amine (L) and L-2 = 2-[2-(3,5-dimethyl-pyrazol-1-yl)-1-methyl-ethyl]-pyridine), exhibited phenoxazinone synthase activity in methanol in the range 5-54 h(-1). Binuclear copper(II) derivatives 3 and 4 show better catalytic activities than manganese(II) and cobalt(II) derivatives. The kinetic studies reveal that phenoxazinone chromophore is produced via a complex-substrate intermediate. Further, 3 and 4 show catecholase activity in methanol in the presence of oxygen. All the complexes showed potent antimicrobial activity against the tested strains of bacteria and fungi. Complex 1 was synthesized for the first time by mixing L-1 and MnCl2 (1:1) and characterized by single-crystal X-ray crystallography, cyclic voltammetry, density functional theory, and thermogravimetry analysis. The present study suggests that napthyl/pyridyl-anchored pyrazole metal complexes are interesting scaffolds for the development of novel model compounds for biochemical reaction and efficient antimicrobial agents.

keywords

CATECHOL OXIDASE; COORDINATION CHEMISTRY; ANTIMICROBIAL ACTIVITY; COPPER(II) COMPLEXES; MULTIDENTATE LIGANDS; DERIVATIVES; OXIDATION; MONONUCLEAR; MODELS; 2-AMINOPHENOL

subject category

Chemistry

authors

Jana, A; Brandao, P; Jana, H; Jana, AD; Mondal, G; Bera, P; Santra, A; Mahapatra, AK; Bera, P

our authors

acknowledgements

We gratefully acknowledge the grant from Council for Scientific and Industrial Research (CSIR), Government of India through the project [No. 1(2858)/16/EMR - II]. Panskura Banamali College acknowledges the grants received from Department of Science and Technology (DST), Govt. of India through FIST program (Sanction no. SR/FST/College -295 dated 18/11/2015).

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