Imidazoline Derivatives Research Articles

Synthesis of imidazoline-palmitic derivative using MAOS (microwave assisted organic synthesis) method

In this work, imidazoline-palmitic derivative had been successfully synthesized by reacting triethylenetetramine (TETA) with palmitic acid (PA). Synthesis process was performed with solvent free using MAOS (Microwave Assisted Organic Synthesis) method with variation of time reactions. Dean-Stark and reflux methods using xylene as a solvent were also performed as comparisons. The percentage yield of TETA-PA imidazoline was obtained from Dean-Stark at 13 hours (95.80 %), reflux at 13 hours (88.53 %), and MAOS at 11 min (87.74 %). TETA-PA imidazoline then was identified by using thin layer chromatography and melting point analyzer followed by characterization using Fourier Transform Infrared (FTIR), UV-Vis, Proton Nuclear Magnetic Resonance (1H-NMR), and Mass Spectrometry (MS) spectral data. This study provides information regarding comparison method for imidazoline derivative synthesis. For further research, TETA-PA imidazoline can be used as corrosion inhibitor towards carbon steel.

Synthesis of 2-Imidazolines via Palladium-Catalyzed Cyclization Reaction of 2,3-Allenyl Amines and Aryl Iodides

An effective method for the synthesis of polysubstituted 2-imidazoline derivatives via palladium-catalyzed cyclization of 2,3-allenyl amines with aryl iodides is described. This pure domino process allows the formation of new carbon–carbon and carbon–nitrogen bonds in a single synthetic operation.

Visible-light-induced selectivity controllable synthesis of diamine or imidazoline derivatives by multicomponent decarboxylative radical coupling reactions

A visible-light-induced and photoredox-catalyzed three-component selectivity controllable synthesis of vicinal diamines and imidazoles from readily available starting materials under mild reaction conditions has been realized.

A Novel Imidazoline Derivative Used as an Effective Corrosion Inhibitor for Carbon Steel in a CO2/H2S Environment

A Novel Imidazoline Derivative Used as an Effective Corrosion Inhibitor for Carbon Steel in a CO2/H2S Environment

Molecular structure optimization design of inhibitors based on frontier orbitals theory

Imidazoline derivatives with 7 levels of HOMO energy and imidazoline quaternary ammonium salts with 4 different LUMO energy levels were designed by adjusting the hydrophilic and hydrophobic groups of the imidazoline molecule. The changes in adsorption bonding and electron transfer of the imidazoline molecule on the metal surface were calculated by the density functional based tight binding method (DFTB+). It was found that when the HOMO and LUMO energy levels matched the iron Fermi level more closely, the imidazoline molecule could undergo more electron transfer with the iron substrate, thereby forming a stronger adsorption bond with the matrix. The corrosion inhibition performance of the imidazoline groups was further tested by electrochemical impedance spectroscopy (EIS) and scanning electron microscope (SEM). Finally, a clear correspondence between the frontier orbital energy level of the imidazoline molecule and its corrosion inhibition performance was discussed, which could provide an effective solution for designing high performance corrosion inhibitor molecules.

2,4,5-Tris(alkoxyaryl)imidazoline derivatives as potent scaffold for novel p53-MDM2 interaction inhibitors: Design, synthesis, and biological evaluation.

Imidazoline-based small molecule inhibitors of p53-MDM2 interaction intended for the treatment of p53 wild-type tumors are the promising structures for design of anticancer drugs. Based on fragment approach we have investigated a key role of substituents in cis-imidazoline core for biological activity of nutlin family compounds. Although the necessity of the substituents in the phenyl rings of cis-imidazoline has been shown, there are no studies in which the replacements of a halogen by other substituents have been investigated. A series of simple cis-imidazoline derivatives containing halogen, hydroxy and alkoxy-substituents were synthesized. The biological activity of the compounds was studied using assays of cytotoxicity (MTT) and p53 level. It was found that the hydroxyl-derivatives were not cytotoxic whereas the alkoxy analogues were the same or more active as halogen-substituted compounds in cell viability test. The synthesized alkoxy derivatives induced an increase of p53 level and did not promote necrotic cell death in the concentration up to 40 µM.

Myristic acid based imidazoline derivative as effective corrosion inhibitor for steel in 15% HCl medium

There is a high demand of effective and eco-friendly corrosion inhibitor for industrial applications. In an attempt to prepare a benign and effective corrosion inhibitor for acidizing purpose, an imidazoline derivative, N-(2-(2-tridecyl-4,5-dihydro-1H-imidazol-1-yl)ethyl)tetradecanamide (NTETD) was synthesized from myristic acid and diethyleneamine. The characterization of the newly synthesized compound was done using 1H NMR, FTIR, and elemental analysis techniques. NTETD was examined as a corrosion inhibitor for low carbon steel in 15% HCl solution using weight loss, electrochemical impedance spectroscopy (EIS), potentiodynamic polarization (PDP), linear polarization (LPR), scanning electron microscope (SEM), energy dispersive spectroscopy (EDAX), atomic force spectroscopy (AFM), and X-ray photoelectron spectroscopy (XPS) techniques. It was found that, the optimum concentration of NTETD is 300 mg/L. With this concentration, inhibition efficiency above 93% is achievable. Results from PDP show that, NTETD acted as a mixed type corrosion inhibitor but with principal effect on cathodic corrosion half reactions. The calculated value of the adsorption-desorption equilibrium constant (1.015 × 103) reveals a strong bonding between NTETD molecules and the steel surface. The EDAX, FTIR, and XPS results confirm the adsorption of NTETD molecules on the steel surface. SEM and AFM results agree with experimental findings that NTETD is effective in corrosion mitigation of steel in 15% HCl solution. The possible corrosion inhibition mechanism by NTETD has been proposed.

Enhanced corrosion resistance of mild steel in sulphuric acid medium by imidazole derivative: Experimental and computational studies

Abstract The inhibition action of the imidazole derivative on the corrosion of mild steel in 0.5 M Sulphuric acid was investigated by weight loss, polarization, Impedance and SEM. The PZC of mild steel was studied by AC impedance method. The polarization experiment revealed that IDZ is of mixed–type but slightly anodic control. Weight loss results obtained revealed that the imidazoline derivatives performed excellently as corrosion inhibitor with efficiency above 70% at 20ppm at 303 K. The optimum period of inhibition for IDZ was determined by weight loss studies. Its adsorption on mild steel obeys Tempkin isotherm. Quantum chemical parameters and Mulliken charge densities on the optimized structure of imidazoline derivative were calculated using GAUSSIAN 09 with B3LYP / 6-31G (d,p) basis set

Organocatalytic diastereoselective [3+2] cyclization of MBH carbonates with dinucleophiles: synthesis of bicyclic imidazoline derivatives that inhibit MDM2-p53 interaction.

An efficient organocatalytic cyclization strategy was developed to synthesize pharmacologically interesting bicyclic imidazoline derivatives. Morita-Baylis-Hillman carbonates were applied as C3 electrophiles to react with N,C-dinucleophiles for the first time, yielding the desired products in good to excellent yields with outstanding diastereoselectivities. The optically pure bicyclic imidazolines were expeditiously prepared by utilizing the readily available chiral ketene aminals as building blocks. The products were found to inhibit MDM2-p53 binding and cell proliferation. The most potent compound 5c induced the accumulation of MDM2, p53 and p21 proteins in HCT116 cells and blocked interaction between MDM2 and p53.

Corrosion inhibition of mild steel by an effective imidazoline derivative based on waste oil in hydrochloric acid

Corrosion inhibition of mild steel by an effective imidazoline derivative based on waste oil in hydrochloric acid

Phosphine-Catalyzed [3+2] Annulation of β-Sulfonamido-Substituted Enones with Sulfamate-Derived Cyclic Imines.

Phosphine-catalyzed [3+2] annulation of β-sulfonamido-substituted enones and sulfamate-derived cyclic imines has been developed, giving a series of imidazoline derivatives in moderate to excellent yields with good to excellent diastereoselectivities. A scale-up reaction worked well under mild reaction conditions. A possible mechanism was proposed on the basis of the results obtained.

Theoretical analysis of frontier orbitals, electronic transitions, and global reactivity descriptors of M(CO)4L2 type metal carbonyl complexes: a DFT/TDDFT study

Metal carbonyl complexes, which have been known as effective catalysts since early days, find use in many fields both directly and indirectly. Although the use of metal carbonyl complexes as bio-probe and protein labeling agent due to their unique spectroscopic properties is known, metal carbonyls have recently been used as storage and transport carriers of carbon monoxide. These developments have motivated the synthesis of new metal carbonyl complexes. Despite the difficulties in obtaining prediction for the molecular properties of organometallic compounds, DFT-based calculation programs have been able to gain insight into the structural/electronic properties of inorganic and organic molecules. In this study, structural, electronic, and reactivity properties of characterized molybdenum and tungsten carbonyl complexes with benzimidazole and imidazoline derivative ligands were investigated using DFT-based calculation program ORCA.

Investigation on the efficiency of corrosion inhibitor in CO2 corrosion of carbon steel in the presence of iron carbonate scale

In this work, the inhibition efficiency of an imidazoline derivative corrosion inhibitors in CO2 corrosion of carbon steel was investigated in the presence of iron carbonate scale and hydrogen sulfide. The use of corrosion inhibitors is one of the most common controlling techniques for CO2 corrosion of carbon steel in oil and gas industry. One of the imidazoline derivatives was used as a corrosion inhibitor which protects the surface through the film formation mechanism. The investigation material was API 5L X65 carbon steel which was cut from a wet gas transmission pipeline. The internal surface of the pipe was covered with iron carbonate as corrosion product. In order to investigate the inhibitor efficiency, Tafel polarization and electrochemical impedance spectroscopy were done in CO2-saturated 3.5 wt.% sodium chloride solution. According to the results, the existence of iron carbonate film reduced the inhibition efficiency. Furthermore, it was found that in the presence of H2S gas, the inhibition efficiency was decreased due to the decrease in inhibitor adsorption on the surface.

Novel monoamine oxidase inhibitors based on the privileged 2-imidazoline molecular framework

Series of structurally diverse 2-imidazoline derivatives have been synthesized by condensation of substituted aldehydes with ethylenediamine, Pd-catalyzed N-arylation of 2-imidazolines and by the formation of 1,2,4-oxadiazoles and benzoxazepines from 2-imidazoline-containing precursors. The 2-imidazoline derivatives were evaluated as potential inhibitors of human monoamine oxidase (MAO) A and B. Among the 2-imidazolines, good potency inhibitors were discovered with compound 9p (IC50 = 0.012 µM) being the most potent MAO-B inhibitor, while compound 9d (IC50 = 0.751 µM) was the most potent MAO-A inhibitor of the series. These potencies are in the same range as those of reference MAO inhibitors used in the clinic. Among 33 compounds evaluated, 13 exhibited IC50 values in the submicromolar range for the inhibition of an MAO isoform. It is postulated that the imidazoline moieties of some of these inhibitors may be recognized by the imidazoline I2-binding site of MAO. Good potency MAO inhibitors may be useful for the treatment of neuropsychiatric and neurodegenerative disorders such as depression and Parkinson’s disease, and future application for the treatment of prostate cancer, congestive heart failure and Alzheimer’s disease. In addition, high potency 2-imidazoline-derived MAO inhibitors may be used as potential probes for the imidazoline binding sites of the MAOs, as well as to determine alternative binding regions of imidazoline within the MAO active site.

The inhibition of CO2 corrosion of L360 mild steel in 3.5% NaCl solution by imidazoline derivatives

The inhibition of CO2 corrosion of L360 mild steel in 3.5% NaCl solution by imidazoline derivatives

Effect of Alkyl Chain Length on Adsorption Behavior and Corrosion Inhibition of Imidazoline Inhibitors

Inhibition performances of imidazoline derivatives with different alkyl chain length for carbon steel in H2S acid solutions has been studied by polarization curves, AC impedance measurements, current transient, Atomic Force Microscopy (AFM) and Density Functional Theory (DFT) techniques. Results showed that the inhibition occurs through adsorption of the inhibitors molecules on the metal surface. The inhibition efficiency was found to increase with increasing inhibitor’s concentration. Polarization data indicated that these compounds act as mixed-type inhibitors. Computational studies of investigated inhibitors were performed by using Hartree–Fock (HF) and M062X methods which are ab-initio and DFT methods with 6-31G basis set in the gas phase and water. Calculated results indicate that the inferred inhibition efficiency increases with the increasing alkyl chain length, which is well in accordance with reported experimental results.

Analysis of the use of environmentally friendly corrosion inhibitors for mild steel in a carbon dioxide saturated chloride solution via experimental design

In the oil and gas industry, carbon dioxide (CO2) gas dissolved in produced fluids can cause both general and localized corrosion of carbon steel pipelines due to the speciation of carbonic acid. To mitigate corrosion, the injection of inhibitors into the production fluid is one of the most commonly used methods. However, recent changes in regulations has resulted in a requirement for the development of new corrosion inhibitors that conform to European regulations. This paper presents a full two‐level factorial experimental design approach to study individual effects of environmentally friendly classed inhibitor components (phosphate ester, imidazoline, and quaternary amine derivatives) as combined inhibitors and their interactive effects on carbon steel corrosion processes in CO2‐saturated 3.5 wt.% NaCl brine. Through the application of in situ electrochemical monitoring, post‐test interferometry, and scanning electron microscopy (SEM) it was possible to determine the influence of each component within the blends and their effect on both general and localized corrosion. Based on 24 h experiments, the phosphate ester derivative reduced general corrosion rate in all blends; imidazoline derivatives reduced the uniform corrosion rate only when it was at the high level in the blend; and the quaternary amine derivative promoted pitting on the surface.

Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons

Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons

Corrosion inhibition performance of imidazolidine derivatives for J55 pipeline steel in acidic oilfield formation water: Electrochemical, surface and theoretical studies

Abstract Present paper deals with the performance of imidazoline derivatives (ATs) as corrosion inhibitor for J55 steel in oil field formation water saturated with CO2. The inhibition effectiveness of AT-1 was found to 90% at 400 mg/L. Inhibitors addition decreases cathodic as well anodic current densities, and significantly strengthens impedance parameters. Contact angle and SEM/AFM/SECM measurements predicts the hydrophobicity and surface morphology of steel, respectively. Density functional theory (DFT) and molecular dynamic simulation (MD) calculations were performed to investigate the adsorption mechanism of ATs. Radial distribution function (RDF) and the mean-square displacement (MSD) were used to study inhibitor/metal interactions and migration rate of corrosive species, respectively.

Topical decongestants: myth and reality

Nasal breathing plays an important role in the respiratory function, which ensures that a person consumes appropriate levels of air. Nasal obstruction causes a person to consume air mainly through the mouth, which impairs the numerous functions of the nose. This leads first to functional abnormalities, and then to morphological and structural changes. Topical decongestants that have the strongest and fastest effect are the most popular drugs to manage rapidly nasal obstruction. The main nasal decongestants can be divided into two groups: sympathomimetic amines: primary aliphatic, phenolic and non-phenolic compounds, as well as imidazoline derivatives. Among modern vasoconstrictive drugs, Otrivin® complex showed good results. The drug contains xylometazoline and ipratropium bromide. Application of this drug strictly according to the instructions and for no more than 15 days guarantees the absence of severe local and systemic complications.