O-anisidine Research Articles

Synthesis, Characterisation, Invitro anticancer activity of Diazo Derivatives of 1,3,4-oxadiazole

This study delves into the comprehensive evaluation of newly synthesized Diazo Derivatives of 1,3,4-oxadiazole compounds, including Aniline, Ortho nitro aniline, Meta nitro aniline, Ortho anisidine, Meta anisidine, 3-chloro aniline, 2,6-dimethyl aniline, 2,5- dicloro aniline, and 3,5- dichloro aniline, aiming to unravel their potential as antioxidants and anticancer agents. The assessment of antioxidant potential involved the utilization of the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay. The cytotoxic activity of these compounds was assessed against MCF-7 breast cancer cells using the MTT assay. Morphological assessments using acridine orange/ethidium bromide (AO/EB) staining. Results were expressed as IC50 values, with 2,5-dichloro aniline and 3-chloro aniline demonstrating remarkable antioxidant activity, each with an IC50 value of 62.5 µg/mL. Several other compounds also exhibited significant antioxidant properties, albeit with slightly higher IC50 values. Notably, Ortho anisidine and Ortho nitro aniline displayed no substantial inhibitory activity against oxidative stress. The cytotoxic activity of these compounds was assessed against MCF-7 breast cancer cells using the MTT assay, with IC50 values ranging from 62.5 to 1000 µg/mL. 2,5-dichloro aniline and 3-chloro aniline emerged as potent inhibitors, both achieving an IC50 value of 62.5 µg/mL. Aniline, Meta nitro aniline, Meta anisidine, 2,6-dimethyl aniline, and 3,5-dichloro aniline exhibited intermediate inhibitory activity, while Ortho anisidine and Ortho nitro aniline showed no significant inhibition. Morphological assessments using acridine orange/ethidium bromide (AO/EB) staining revealed diverse cellular responses induced by 2,5-dichloro aniline and 3-chloro aniline treatment. These changes align with well-established apoptotic processes observed in therapeutically treated cell lines. This research contributes valuable insights into the antioxidant and anticancer potential of Diazo Derivatives of 1,3,4-oxadiazole compounds, with 2,5-dichloro aniline and 3-chloro aniline emerging as promising candidates for further exploration in combatting oxidative stress and breast cancer. These findings underscore the importance of antioxidants in cancer prevention and the potential therapeutic applications of these compounds.
 Keywords: Diazo Derivatives of 1,3,4-oxadiazole, 2,5-dichloro aniline, 3-chloro aniline, DPPH, MTT assay, MCF-7

The green synthesis of oligo(azomethine)s based on p-anisidine and o-anisidine: reaction conditions, electrochemical and thermal properties

Schiff bases and their conjugated oligo(azomethine)s have been synthesized via condensation and oxidative polycondensation of o-anisidine (OA) with 2-hydroxy-1-naphthaldehyde (2-HNA) and p-anisidine (PA) with 4-hydroxy benzaldehyde (4-HBA), respectively. The oxidative polycondensation reaction conditions of 1-[(2-methoxyphenylimino)methyl]naphthalen-2-ol (1,2-MPIMN) and 4-[(4-methoxyphenylimino)methyl]phenol (4,4-MPIMP) were studied by oxidants such as air and aqueous solutions of H2O2 and NaOCl in different concentrations in an aqueous alkaline medium between 50 °C and 90 °C at different reaction times. The structures of polymers were confirmed by FT-IR, UV-Vis and 1H-13C-NMR measurements. The molecular weights and surface morphologies of oligomers were determined by size exclusion chromatography (SEC) and scanning electron microscopy (SEM), respectively. Electrochemical and thermal features of compounds were studied using UV-Vis spectroscopies, cycling voltammetry (CV), and TG-DTA. The mass losses values ​​of the 1,2-MPIMN, oligo(1,2-MPIMN), 4,4-MPIMP, and oligo(4,4-MPIMP) were calculated from the thermogravimetric curves as 98.00%, 53.52%, 69.00%, and 58.70%, respectively, at 1000 °C. The HOMO, LUMO levels, electrochemical (E’ g ), and optical band gap energies (Eg ) values of the compounds were calculated from CV and UV-Vis data. The E’ g values of 1,2-MPIMN, oligo(1,2-MPIMN), 4,4-MPIMP, and oligo(4,4-MPIMP) were found to be 2.64, 1.54, 2.31, and 2.16 eV, respectively. The electrical properties of monomers and oligomers were determined at room temperature.

Development of poly(o-anisidine-co-ethyl 4-aminobenzoate) conducting film for electrochromic and biosensor applications

Copolymers of o-anisidine (OA) and ethyl 4-aminobenzoate (EAB) were synthesized by chemical polymerization in various molar ratios of ethyl 4-aminobenzoate in 1 M HCl aqueous solution, using potassium persulphate as an oxidant. Spectroelectrochemical analysis of the copolymer film, the colour of the copolymer thin films changes from yellow (at −0.2 to 0.0 V) to green (0.2–0.6 V) and to blue (0.8 V). Also, the copolymer was examined for dopamine sensing and it exhibited significant results with detection range from 8 × 10−8 to 1.40 × 10−5 M and the lower limit of detection determined is 1 × 10−8 M which shows the possibility of low and high concentrations.

Mechanistic insights of the degradation of an O-anisidine carcinogenic pollutant initiated by OH radical attack: theoretical investigations

O-Anisidine (O-AND) is one of the amino organic compounds that harm human health, and is considered as a carcinogenic chemical.

Electro-Catalytic Oxidation of Methanol at Ni(OH)2 Nanoparticles-Poly (o-Anisidine)/Triton X-100 Film onto Phosphotungstic Acid-Modified Carbon Paste Electrode

In this work, Phosphotungstic Acid modified Carbon Paste Electrode (PWA-CPE) is used as a substrate for electro-polymerization of o-Anisidine (OA). Also, Triton X-100 (TX-100) surfactant is used as an additive for electrochemical polymerization of OA onto the PWA-CPE, which is investigated as a novel matrix for dispersion of nickel species. The prepared electrodes are characterized by scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), and electrochemical methods. Growth of the poly o-Anisidine (POA) film in the absence of TX-100 and/or PWA is very poor, while it considerably increases in the presence of them. The methanol oxidation and stability of the Ni/POA (TX-100)/PWA-CPE are investigated by various electrochemical techniques. It has been shown that the poly (o-Anisidine)/Triton X-100 (POA (TX-100)) at the surface of PWA-CPE improves the catalytic efficiency of the dispersed Ni(OH)2 nanoparticles towards methanol oxidation.

Investigation of the Corrosion Behavior of Poly(Aniline-co-o-Anisidine)/ZnO Nanocomposite Coating on Low-Carbon Steel

A copolymer of aniline (AN) and o-anisidine (OA), Poly(AN-co-OA) and its nanocomposite with ZnO nanoparticles, Poly(AN-co-OA)/ZnO were synthesized by chemical oxidative polymerization using ammonium persulfate as an oxidant in hydrochloric acid medium. The synthesized compounds were characterized using FTIR, XRD, SEM-EDS, TEM, and electrical conductivity techniques. The copolymer and nanocomposite were separately dissolved in N-methyl-2-pyrrolidone and were casted on low-carbon steel specimens using 10% epoxy resin as a binder. The anticorrosive properties of the coatings were studied in different corrosive environments such as 0.1 M HCl, 5% NaCl solution, and distilled water at a temperature of 30 °C by conducting corrosion tests which include immersion test, open circuit potential measurements, potentiodynamic polarization measurements, and atmospheric exposure test. The surface morphology of the coatings prior to and after one-month immersion in corrosive solution was evaluated using SEM. It was observed that the nanocomposite coating exhibited higher corrosion resistance and provided better barrier properties in comparison with copolymer coating. The presence of ZnO nanoparticles improved the anticorrosion properties of copolymer coating in all corrosive media subjected to investigation.

Inclusion complexes of ortho-anisidine and β-cyclodextrin: A quantum mechanical calculation

Abstract The structural aspects for the complexation of ortho-anisidine (O-AN)/β-cyclodextrin were explored by using PM6, density function theory B3LYP/6-31G*, M05-2X/6-31G*, B3PW91/6-31G*, MPW1PW91/6-31G*, HF/6-31G* methods and several combinations of ONIOM2 hybrid calculations. Calculations were performed upon the inclusion complexation of β-cyclodextrin (β-CD) with neutral (O-AN1) and cationic (O-AN2) species of ortho-anisidine. The obtained results with PM6 method clearly indicate that the formed complexes are energetically favored, the complex of O-AN2/β-CD in B orientation is significantly more favorable than the others energetically. The structures show the presence of several intermolecular hydrogen bond interactions that were studied on the basis of natural bonding orbital (NBO) analysis, employed to quantify the donor–acceptor interactions between ortho-anisidine and β-CD.

A New and Simple Electrocatalyst for Formaldehyde Oxidation; Nickel/poly(o‐Anisidine)/Film Modified Ionic Liquid Carbon Paste Electrode

AbstractIn present work, the ionic liquid, 1‐butyl‐3‐methylimidazolium bis (trifluoromethylsulfonyl) imide was incorporated in the carbon paste electrode as the binder (IL‐CPE). O‐anisidine (OA) monomer is electropolymerized in the presence of an aqueous acidic solution onto IL‐CPE (POA/IL‐CPE). The as‐prepared substrate is used as a porous matrix for dispersion of Ni(II) ions by immersing the modified electrode in a nickel(II) nitrite solution. The modified electrodes are characterized by scanning electron microscopy (SEM) and electrochemical methods. The POA/IL‐CPE was applied successfully to highly efficient (current density of 18.2 mA cm−2) electrocatalytic oxidation of formaldehyde in alkaline medium. Finally, the rate constant for chemical reaction between formaldehyde and redox sites of the electrode was calculated.

Carbon Nanotubes Reinforced Conducting Polyaniline And Its derivative Poly(o-anisidine) Composites

Conducting polymer nanocomposites (PANI-CNT and POAS-CNT) have been synthesized by polymerization of aniline (ANI)/ o-anisidine (OAS) in the presence of functionalized multiwall carbon nanotubes (MWCNTs). These nanocomposites have been characterized by UV-VIS, FTIR and SEM to study the effect of incorporation of MWCNTs on the morphology, structure and crystalline of the conducting polyaniline and its substitute derivate poly(o-anisidine). UV-VIS spectra shows that polaron-π* and π-π* transition bands of the PANI/POAS chain shifted to longer wavelengths, indicating the interaction between quinoid rings and MWCNTs. FTIR spectra shows that the interaction between the MWCNTs and PANI/POAS may result in ‘charge transfer’, whereby the sp2 carbons of the MWCNTs compete with dopant ions [Cl – ] and perturb the H-bond, resulting an increase in the N-H stretching intensity. Electron microscopy reveals that the interaction between the quinoid ring of PANI/POAS and the MWCNTs causes PANI and POAS polymer chains to be adsorbed at the surface of MWCNTs, thus forming a tubular core surrounding the MWCNTs. The nanocomposites showed high electrical conductivity compared to pure PANI/POAS. Further, PANI-CNT showed high electrical conductivity compared to that of POAS-CNT.

Potentiostatic Deposition of Conducting Poly(Aniline-Co-O-Anisidine) Coating on Low Carbon Steel and its Corrosion Performance

Conducting poly(aniline-co-o-anisidine) coatings were synthesized on low carbon steel by electrochemical polymerization of aniline and o-anisidine in aqueous oxalic acid by using potentiostatic method. The characterization of these coatings were carried out by using scanning electron microscopy. The corrosion protection performance of these coatings were evaluated by using potentiodynamic polarization technique. It was found that uniform and adherent conducting poly (aniline-co-o-anisidine) coating can be obtained on low carbon steel using potentio static technique. The potentiodynamic polarization study reveals that the coating offers significant corrosion protection to low carbon steel in acidic medium.

Growth behavior of poly( o-anisidine-co-o-toluidine) deposition by cyclic voltammetry

Electrochemical co-polymerization of o-anisidine (OA) with o-toluidine (OT) was carried out in 1 M H2SO4 by cyclic voltammetry. Polymeric films were deposited by employing different conditions such as cycle number and feed ration of co-monomers. Electrochemical homo-polymerization of OA with OT were also done. A growth equation for co-polymer deposition relating parameters of operation and charge associated for film deposition was obtained. The growth rate constant was also determined.

Growth Behavior of Poly(o-Anisidine-Co-Aniline) Deposition by Cyclic Voltammetry

Electrochemical copolymerization of o-anisidine (OA) with aniline (A) was carried out in 1 M H2SO4 by cyclic voltammetry. Polymeric films were deposited by employing different conditions such as cycle number and mole ratio of comonomers. Electrochemical homopolymerization of o-anisidine with aniline were also done. A growth equation for copolymer deposition relating parameters of operation and charge associated for film deposition was obtained. Growth rate constant was determined.

Poly( o-anisidine) coatings on copper: synthesis, characterization and evaluation of corrosion protection performance

The poly( o-anisidine) (POA) coatings were synthesized on copper (Cu) by electrochemical polymerization (ECP) of o-anisidine (OA) and their corrosion protection performance in an aqueous solution of 3% NaCl was investigated by potentiodynamic polarization technique. The ECP of OA was carried out under cyclic voltammetric conditions from an aqueous solution of sodium oxalate to generate strongly adherent and smooth POA coatings on Cu substrates. These coatings were characterized by cyclic voltammetry (CV), UV-vis absorption spectroscopy, Fourier transform infrared (FTIR) spectroscopy, scanning electron microscopy (SEM) and X-ray diffraction (XRD) measurements. The optical absorption spectroscopy study reveals the formation of the mixed phase of pernigraniline base (PB) and emeraldine salt (ES) form of POA. The potentiodynamic polarization curves were used to evaluate the ability of the POA coatings to protect the Cu surface. The potentiodynamic polarization curves show that the POA coating increases the corrosion potential and drastically reduces the corrosion rate of copper. The corrosion rate of POA coated Cu is ∼100 times lower than that observed for bare Cu.

Investigations on growth mechanism of poly( o-anisidine) coatings on low carbon steel by electrochemical synthesis method

The growth mechanism of poly( o-anisidine) (POA) coating on low carbon steel (LCS) substrates has been investigated. In this work, the POA coatings on LCS substrates have been synthesized by electrochemical polymerization (ECP) of o-anisidine (OA) under galvanostatic conditions from aqueous solution of oxalic acid at room temperature (27 °C) and 40 °C. At room temperature, uniform and strongly adherent dark green POA coatings were obtained on LCS substrates. These coatings were characterized by potential–time ( E– t) curves, X-ray diffraction (XRD) measurements, Fourier transform infrared (FTIR) spectroscopy, scanning electron microscopy (SEM) and UV-visible absorption spectroscopy. The E– t curves in conjunction with FTIR, XRD and SEM studies clearly reveal that the growth of POA coatings on the LCS occurs in three distinct stages: (i) an induction time for ECP, (ii) passivation of LCS electrode surface via the formation of polycrystalline iron oxalate (FeC 2O 4, 2H 2O) interphase and (iii) decomposition of the interphase followed by ECP of OA. However, at 40 °C with an applied current density ∼0.66 mA cm −2, the E– t curve shows the undesirable behavior, which is attributed to non-decomposition of the interphase during the third growth stage. As a consequence, at 40 °C the ECP of OA has not occurred on the LCS electrode surface. Thus, the formation of the interphase and its subsequent decomposition is necessary for the ECP of OA to occur on the LCS electrode surface.

Influence of synthesis temperature on electrochemical polymerization of o-anisidine on low carbon steel

The influence of synthesis temperature on the electrochemical polymerization (ECP) of o-anisidine (OA) on low carbon steel (LCS) has been investigated. The ECP of OA was carried out on LCS substrate under galvanostatic conditions from aqueous solution of oxalic acid at various temperatures between 0 and 40 °C. The resulting poly( o-anisidine) (POA) coatings were characterized by potential–time ( E– t) curves, UV–VIS absorption spectroscopy, scanning electron microscopy (SEM) and X-ray diffraction (XRD) measurements. The E– t curves reveal that the synthesis of POA coating at 0, 15 and 27 °C on LCS occurs in three stages, an induction time for ECP, passivation of LCS electrode surface via the formation of iron oxalate (FeC 2O 4·2H 2O) interphase and the dissolution of interphase and followed by ECP of OA. However, at 40 °C with an applied current density ∼0.66 mA/cm 2, the E– t curve shows the undesirable behavior which is attributed to non-decomposition of interphase during the third growth stage. As a consequence, at 40 °C the ECP of OA has not occurred on the LCS electrode surface. The XRD, SEM and optical absorption spectroscopy support this observation. It has been found that, as the synthesis temperature is increased, at low current densities, the induction time is observed to decrease, whereas it does not show any significant change at higher current densities. The optical absorption spectroscopy reveals the formation of mixed phase of emeraldine salt (ES) and pernigraniline base (PB) at 27 °C, whereas at lower temperatures the major portion of the coating constitutes the ES phase. The surface morphology, as revealed by SEM is observed to depend on the synthesis temperature.

Synthesis and properties of poly(aniline- co-anisidine)

Aniline and ortho—anisidine were chemically copolymerized at various temperatures and monomer compositions. Copolymers completely soluble in THF are prepared and characterized.

Mutagenicity of o-anisidine to the bladder of lacI- transgenic B6C3F1 mice: absence of 14C or 32P bladder DNA adduction.

Earlier studies have established that the rodent bladder carcinogen o-anisidine (OA) gives negative results in all of the standard rodent genetic toxicity assays. In the present study, a single oral administration of the maximum tolerated dose level (750 mg/kg) of OA to B6C3F1 mice yielded negative results in 32P-post-labelling assays of bladder and liver DNA (24 h after dosing). Likewise, 14C-ring-labelled OA administered orally to B6C3F1 mice gave no evidence of DNA binding 6, 12 or 24 h later. Administration of OA (750 mg/kg) to transgenic lacI- mice (Big Blue) led to a small increase in mutation frequency (MF) in the bladder, but not in the liver. Increased MFs were observed in the bladder following 1, 3 or 10 daily doses with sampling times of 1 or 2 weeks after the final dose. However, statistical significance (P < 0.01) was only reached 2 weeks after either 3 or 10 daily administrations of OA. The positive control chemical (dimethylnitrosamine) gave a positive result (P < 0.01) in the liver, but not the bladder, 7 days after a single administration of 10 mg/kg. The possibility that OA is mutagenic and carcinogenic to the rodent bladder via formation of radical species is suggested.

Reaction of 2,4-dinitrofluorobenzene with o-anisidine in benzene. Further evidence of the "dimer" mechanism

Reaction of 2,4-dinitrofluorobenzene with o-anisidine in benzene. Further evidence of the "dimer" mechanism

Manganese(II) Catalysed Oxidation of Aromatic Amines by Hydrogen Peroxide and lts Application to the Chelatometric Determination of Manganese

Manganese(II)catalyses the hydrogen peroxideoxidation of aromatic amines such as phenetidine, P-anisidine, o-anisidi ne, etc, in aqueous carbonate so1utions, Cgbalt(II) and copper(ll) catalyse also the reaction in sodium bicarbonate (pH 8.4) and in ammonium carbonate solution (pH 9.3), respectively. This catalytic reaction was utilized to indicate the end'point of titration in the determinationof Mn(II)with EDTA.The optimum of the catalytic action of manganese(II)ion was found to be limited to relatively high carbonate concentration (O.4 mol/1) and narrow pH ranges (between 8 and 9.5), The recommended procedure for manganese determination was as follows to about 50 ml portion of O.4 mol/l carbonate solution containing known amounts of EDTA, add 3 ml'of O.2% P phenetidine (or P-anisidine) and 1 ml of 3% hydrogen peroxide. Titrate the solution with manganese(ll) solution. At the end point, the solution turned deep orange immediately by the formation of quinoneimines.this catalytic titration method was applied to determine zinc, cadmium, mercury and lead by'back-titrationof excess of EDTA with standard manganese(II)solution. The results were in good agreement with those obtained by the titrimetric method using BT or XO as metal indicator.The catalytic titration of manga: nese(II)with o-dianisidine and o-tolidine was also investigated.