Mononuclear Co(III), Ni(II) and Cu(II) complexes of tridentate di‐tert‐butylphenylhydrazone: Synthesis, characterization, X‐ray crystal structures, Hirshfeld surface analysis, molecular docking and in vivo anti‐inflammatory activity

Abstract

A new hydrazone (LH 2 ) derived from the condensation of 2-(4-fluorobenzamido) benzohydrazide with 3,5-di-tert-butyl-2-hydroxybenzaldehyde was used to synthesize Co(III), Ni(II) and Cu(II) complexes. These were characterized using various physicochemical, thermal, spectroscopic and single-crystal X-ray diffraction techniques. All the complexes crystallize in a monoclinic crystal system with P2 1 /n space group and Z = 4. Structural studies of [Co(L)(LH)]⋅H 2 O indicate the presence of both amido and imidol tautomeric forms of the ligand, resulting in a distorted octahedral geometry around the Co(III) ion. On the other hand, in the [Ni(L)(DMF)] and [Cu(L)(H 2 O)] complexes, the ligand coordinates to the metal through imidol form resulting in distorted square planar geometry, in which the fourth position is occupied by the oxygen of coordinated DMF in [Ni(L)(DMF)] and by a water molecule in [Cu(L)(H 2 O)]. Hirshfeld surface calculations were performed to explore hydrogen bonding and C-H⋅⋅⋅π interactions.Molecular docking studies were carried out to study the interaction between the synthesized compounds and proteins (cyclooxygenase-2 and 5-lipoxygenase). The complexes along with the parent ligand were screened for their in vivo anti-inflammatory activity, using the carrageenan-induced rat paw oedema method. The complexes show significant anti-inflammatory potencies.

Mononuclear Co(III), Ni(II) and Cu(II) complexes of 2‐(2,4‐dichlorobenzamido)‐N'‐(3,5‐di‐tert‐butyl‐2‐hydroxybenzylidene)benzohydrazide: Structural insight and biological assay

“…LH 3 was prepared in three steps as reported earlier in a similar case . In the first step, methyl anthranilate ( 1 ; 3.02 g, 20 mmol) was suspended in benzene (300 ml), to which 2,4‐dichlorobenzoyl chloride (4.16 g, 20 mmol) was added and stirred for 3 h at room temperature to generate methyl 2‐(2,4‐dichlorobenzamido)benzoate ( 2 ; yield: 91%), which was then hydrazinolyzed at reflux temperature to produce 2‐(2,4‐dichlorobenzamido)benzohydrazide ( 3 ; yield: 76%).…”

Combined Alkylating Agents as a Resolution for Highly Selective N-Alkylation of 2-Hydroxybenzaldehyde Acylhydrazones

“…6 Moreover, metal complexes of the acylhydrazones of salicylaldehyde or substituted salicylaldehydes have been showed to have antioxidant and antiproliferative potency. 7 As such, these complexes might be potentially useful for the treatment of cancer, 8,9 Alzheimer's disease, 10 inflammation, 11 or diseases caused by Gram-positive bacteria. 12 Previous studies have shown that the introduction of a methyl group onto the acylated nitrogen atom of acylhydrazones can lead to distinct biological responses.…”