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Synthesis, structural characterization and biological evaluation of mononuclear transition metal complexes of zwitterionic dehydroacetic acid N ‐aroylhydrazone ligand
Author(s) -
Kendur Umashri,
Chimmalagi Geeta H.,
Patil Sunil M.,
Gudasi Kalagouda B.,
Frampton Christopher S.
Publication year - 2018
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4278
Subject(s) - chemistry , octahedral molecular geometry , ligand (biochemistry) , square pyramidal molecular geometry , crystallography , tetrahedral molecular geometry , stereochemistry , nickel , crystal structure , agarose gel electrophoresis , metal ions in aqueous solution , metal , single crystal , dna , organic chemistry , receptor , biochemistry
Synthesis and characterization of mononuclear transition metal complexes viz., Co(II), Ni(II), Cu(II) and Zn(II) with a newly designed ligand, ( E )‐2‐benzamido‐ N' ‐(1‐(2‐hydroxy‐6‐methyl‐4‐oxo‐4H‐pyran‐3‐yl) ethylidene) benzohydrazide ( H 2 L ) are reported. Molecular structures of H 2 L , Ni(II) and Cu(II) complexes were determined by single‐crystal X‐ray diffraction studies. The structures were stabilized by various intra/inter‐molecular H‐bonding, C‐H···π and π···π stacking interactions. H 2 L exists in zwitterionic form and acts in a monoanionic manner. Ligand/metal ratio was 2:1 for cobalt, nickel and zinc, whereas 1:1 for the copper complex. Co(II), Ni(II) and Zn(II) complexes display distorted octahedral geometry, while the Cu(II) complex shows distorted square pyramidal geometry around the metal ion. Hirshfeld surface analysis and 2D fingerprint plots revealed that H 2 L and its complexes were supported mainly by H⋯H, O⋯H and C⋯H intermolecular interactions. The synthesized compounds were screened for in vitro anti‐inflammatory activity by gelatin zymography and the activity was comparable with tetracycline. Their cleavage behavior towards calf thymus DNA has been studied using agarose gel electrophoresis method. H 2 L and Cu(II) complex were selected by National Cancer Institute (NCI) for in vitro single dose testing in the full NCI 60 cell lines panel assay. Finally, molecular docking simulation effectively proves the binding of all the synthesized compounds at cyclooxygenase‐2 (COX‐2) active sites.