Synthesis, Chemical Characterization, DNA Binding, Antioxidant, Antibacterial, and Antifungal Activities of Ferrocence Incorporated Selenoureas

Abstract

Ferrocene-incorporated selenoureas 1-(4-methoxybenzoyl)-3-(4-ferrocenylphenyl)selenourea (P4Me), 1-(3-methoxybenzoyl)-3-(4-ferrocenylphenyl)selenourea (P3Me), and 1-(2-methoxybenzoyl)-3-(4-ferrocenylphenyl)selenourea (P2Me) were synthesized and characterized by nuclear magnetic resonance, Fourier transform infrared spectroscopy, atomic absorption spectroscopy, CHNS, and single-crystal X-ray diffraction. DNA interaction of the compounds was investigated with cyclic voltammetry, UV-visible spectroscopy, and viscometry, which is a prerequisite for anticancer agents. Drug-DNA binding constant was found to vary in the sequence: K(P4Me) (4.9000 × 10⁴ M⁻¹) > K(P2Me) (2.318 × 10⁴ M⁻¹) > K(P3Me) (1.296 × 10⁴ M⁻¹). Antioxidant (1,1-diphenyl-2-picrylhydrazyl), antifungal (against Faussarium solani and Helmentosporium sativum), and antibacterial (against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Bacillus subtilis) activities have also been reported in addition.

Ferrocene incorporated selenoureas as anticancer agents

“…In 1 H NMR spectra publications [12,13] but details cancer studies are the main concern in this manuscript.…”

“…The resulting orange colored solution was mixed with cold water under constant magnetic stirring. This removed the potassium chloride suspension and precipitated the product which was then filtered, dried and washed with n-hexane and methanol[1,[10][11][12][13][14][43][44][45][46].…”

DNA-binding studies and biological activities of new nitrosubstituted acyl thioureas

“…The decrease in the absorption of 1,1-diphenyl-2-picrylhydrazyl (DPPH) was monitored to calculate the percentage scavenging according to the following formula [17]:…”

“…The methyl and methoxy protons, of TU2 and TU3 respectively, gave an additional singlet, in their H 1 NMR spectra. In all of the synthesized thioureas, the -NH proton situated in between phenyl ring and C=S, is maximum desheilded owing to the intramolecular hydrogen bonding and thus gave a singlet at around 13 ppm and the -NH proton located in between the C=O and C=S is deshielded to a lesser extent thus providing a singlet in the region of 10-11 ppm[8,[15][16][17]. The aromatic ring protons gave their signals between 8 and 9 ppm.…”

A new class of silica-supported chromo-fluorogenic chemosensors for anion recognition based on a selenourea scaffold

“…However, in this scenario, and, to the best of our knowledge, examples of selenourea-based anion sensors have never been reported in the literature to date despite selenoureas are interesting organoseleno compounds that show anticancer activity, antioxidant properties, enzyme inhibition, and DNA binding properties. [16][17][18][19][20] Taking these concepts into account and following our interest in anion recognition and sensing [21][22][23][24][25] we decided to explore the potential use of selenoureas as a new scaffold for the design of anion chemosensors.In particular, here, we describe the ability of the asymmetric 1-(4-methyl-2-oxo-2H-chromen-7-yl)-3-phenylselenourea (L) to act as a colorimetric and/or fluorescent sensor for S 2-and CNrecognition. L was obtained according to the reaction shown in Scheme 1.…”