Design, Synthesis and X‐ray Crystal Structure of Iodinated Benzoboroxole Derivatives by Consecutive Metal–Iodine Exchange of 3,4,5‐Triiodoanisole

A series of Cu(II), Co(II), Pd(II), Pt(II), Zn(II), Cd(II) and Fe(III) complexes were designed and synthesized using Schiff base 1‐phenyl‐2,3‐dimethyl‐4‐(N‐3‐formyl‐6‐methylchromone)‐3‐pyrazolin‐5‐one (HL). The new metal complexes were investigated using various physicochemical techniques including elemental and thermal analyses, molar electric conductivity and magnetic susceptibility measurements, as well as spectroscopic methods. Also, the crystal structures of ligand HL and the Pd(II) complex were determined using single‐crystal X‐ray diffraction analysis. For all compounds, the antimicrobial activity was studied against a series of standard strains: Staphylococcus aureus, Bacillus cereus, Enterococcus faecalis, Escherichia coli, Acinetobacter baumannii, Candida albicans, Candida krusei and Cryptococcus neoformans. The in vitro antiproliferative activity of the ligand and complexes was evaluated against ten cancer cell lines: MSC, A375, B16 4A5, HT‐29, MCF‐7, HEp‐2, BxPC‐3, RD, MDCK and L20B. At 10 μM concentration a significant cytotoxic effect of the Co(II), Pd(II) and Cd(II) complexes was observed against B16 4A5 murine melanoma cells. The Zn(II) complex is active against HEp‐2, RD and MDCK cancer cell lines, where IC50 values vary between 1.0 and 77.6 and for BxPC‐3 the activity index versus doxorubicin is 3.7 times higher.

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, molecular docking studies and in vitro screening of new metal complexes with Schiff base as antimicrobial and antiproliferative agents

Pahontu

Proks

Shova³

et al. 2019

“…[14][15][16] These properties of Schiff bases and their complexes have resulted in wide applications in the biological field [17] Cu (II) complexes are known to be effective against rheumatoid arthritis and they also show anti-ulcer activity. [18] This is because gastrointestinal irritation often precludes treatment by other antiarthritic drugs. This is due to role of copper in preventing gastrointestinal damage by acidic anti-inflammatory agents.…”

Section: Introductionmentioning

confidence: 99%

A new azo‐Schiff base: Synthesis, characterization, biological activity and theoretical studies of its complexes

Zoubi

Al‐Hamdani

Ahmed

et al. 2017

A new Azo-Schiff base ligand L was prepared by reaction of m-hydroxy benzoic acid with (Schiff base B) of 3-[2-(1H-indol-3-yl)-ethylimino]-1.5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylamine. This synthesized ligand was used for complexation with different metal ions like Ni(II), Co(II), Pd(II) and Pt(IV) by using a molar ratio of ligand: metal as 1:1. Resulted compounds were characterized by NMR ( 1 H and 13 C), UV-vis spectroscopy, TGA, FT-IR, MS, elemental analysis, magnetic moment and molar conductivity studies. The activation thermodynamic parameters, such as ΔE*, ΔH * , ΔS * , ΔG * and K are calculated from the TGA curves using Coats-Redfern method. Hyper Chem-8 program has been used to predict structural geometries of compounds in gas phase. The biological activities of Schiff base and its complexes had been tested in vitro against, two Gram positive bacteria (Bacillus subtillis and Staphylococcus aureus) and two Gram negative bacteria (Escherichia coli and Pseudomonas aeruguinosa).

“…For example, Hemoglobin, is an iron‐containing protein, binds to oxygen and transports it to all tissues . Furthermore, macrocyclic Cr 3+ complexes are famous for their biological influences as anticarcinogenic, antibacterial, and antifungal properties . Manganese and its compounds are widely used in analytical chemistry, metallurgical processes, paints, pigment industry, adsorption into the soil for plant growth and as a catalyst in the replication and transcription of DNA as well as coenzyme (i.e.…”

Section: Introductionmentioning

confidence: 99%

Macrocyclic Cr³⁺, Mn²⁺ and Fe³⁺ complexes of a mimic SOD moiety: Design, structural aspects, DFT, XRD, optical properties and biological activity

El‐Gammal

El-Brashy

El‐Reash

2020

A novel SOD‐like macrocycle “H2DPD” and its trivalent chromium, iron and divalent manganese complexes have been isolated and characterized using the conventional tools. The macrocycle was prepared by 2:2 condensation of P‐phenylenediamine with 5,5‐dimethyl1,3‐cyclohexanedione. IR and electronic spectral data suggested that H2DPD coordinates to the metal ion as N4 tetradentate donor with two Cl− occupying the remaining two sites of the distorted octahedron. XRD spectrum of Cr3+ complex indicated that the complex crystallizes in a face‐centered monoclinic structure with lattice parameters: a = 10.9380 Å; b = 12.4870 Å; c = 12.4600 Å, α = γ = 90° and β = 111.430 with space group P 1 21/c 1 (14). The energy gap (EHOMO‐ELUMO), molecular electrostatic potential map (EPM) of title compounds, bond length, bond angle, as well as global and local reactivity were estimated using DFT method. The Eg values obtained from electronic spectra of Cr3+, Mn2+ and Fe3+ complexes were found to be 1.284, 1.220 and 1.138 eV, respectively which are in accordance with those evaluated by DFT revealing semiconductor nature. Also, the thermal degradation of all title compounds was carried out and the kinetic parameters were evaluated using Coats‐Redfern and Horowitz‐Metzger equations. Moreover, the compounds have screened for antibacterial as well as superoxide mimic activities. Cr3+ complex exhibited the most significant potent activity against all bacterial strains. With respect to SOD‐like activity, the macrocycle showed the most remarkable SOD‐like activity comparable to the standard drug, ascorbic acid.