Imidazoline derivatives: a patent review (2006 – present)

Guan, Xianghong; Hu, Yongzhou

doi:10.1517/13543776.2012.727397

Cited by 16 publications

(8 citation statements)

References 69 publications

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“…68 It can be observed that for both EIS and the PDP data, the slope and the regression coefficient are close to unity, which supports the validity of the Langmuir isotherm. The K ads was used to calculate the standard free energy of adsorption (ΔG ads 0 ): 69,70 5 ) ads 0 ads (7) where the symbols R and T have their usual meaning, and the value 55.5 provides the molar concentration of water. The calculated ΔG ads 0 values from the EIS and PDP data are −31.78 and −32.06 kJ mol −1 , respectively, showing that the adsorption of the inhibitor molecules on the steel substrate obeys a mixed mode of physical and chemical adsorption.…”

Section: Resultsmentioning

confidence: 99%

“…To counter this issue, a number of organic compounds are introduced as additives in the corrosive solution to minimize the damage caused to the steel structures. Most of the research and development in the area of sweet corrosion inhibitors have been reported on the use of imidazoline-based corrosion inhibitors. , It should be noticed that these molecules require a tedious synthesis procedure, are expensive, and are highly toxic. Therefore, considering the environmental constraints, there is a lot of research work currently undergoing in the area of environment-friendly corrosion inhibitors. , …”

Section: Introductionmentioning

confidence: 99%

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Electrochemical and Computational Insights on the Application of Expired Metformin Drug as a Novel Inhibitor for the Sweet Corrosion of C1018 Steel

et al. 2020

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An expired metformin drug (MET) was used as a corrosion inhibitor for C1018 carbon steel in a CO2-saturated 3.5 wt % NaCl + 340 ppm acetic acid solution under static conditions. The inhibitor was evaluated using electrochemical methods complemented with surface analytical measurements and computational modeling. The drug displayed a high inhibition efficiency of ∼90% at 200 ppm. Impedance analyses revealed a rise in the charge transfer resistance at the steel–solution interface upon the addition of the inhibitor. Polarization measurements suggested that MET acted more like a cathodic-type corrosion inhibitor and significantly reduced the corrosion current density. The adsorption of MET on the steel substrate followed the Langmuir isotherm, showing a mixed type of physical and chemical modes of adsorption. The thermodynamic parameters revealed strong and spontaneous adsorption on the steel surface. The surface analysis using SEM supported the inhibitor adsorption on the steel substrate. Based on the DFT simulation, inhibition by MET is mainly achieved by its protonated form, which leads to the formation of a thin film on the steel surface rather than the modification of the work function of the steel surface. The experimental and theoretical estimations of pKa complemented the DFT results, both agreeing that the monoprotonated form of MET is the dominant form in which the inhibitor adsorbs on the steel surface to form a thin film rather than modify the work function of the steel surface.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Electrochemical and Computational Insights on the Application of Expired Metformin Drug as a Novel Inhibitor for the Sweet Corrosion of C1018 Steel

et al. 2020

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“…Nevertheless, these studies helped establishing that changing N 1 side chain interferes mainly with PK properties but also with potency [ 62 , 63 ]. Several other analogs are disclosed in patents from Hoffman-La Roche, presenting the same imidazoline core and other structure variations such as imidazopyridinones [ 30 , 39 , 64 , 65 ]. Moreover, Miyazaki et al .…”

Section: Reactivation Of P53 As a Therapeutic Strategymentioning

confidence: 99%

Chemical Variations on the p53 Reactivation Theme

et al. 2016

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Among the tumor suppressor genes, p53 is one of the most studied. It is widely regarded as the “guardian of the genome”, playing a major role in carcinogenesis. In fact, direct inactivation of the TP53 gene occurs in more than 50% of malignancies, and in tumors that retain wild-type p53 status, its function is usually inactivated by overexpression of negative regulators (e.g., MDM2 and MDMX). Hence, restoring p53 function in cancer cells represents a valuable anticancer approach. In this review, we will present an updated overview of the most relevant small molecules developed to restore p53 function in cancer cells through inhibition of the p53-MDMs interaction, or direct targeting of wild-type p53 or mutated p53. In addition, optimization approaches used for the development of small molecules that have entered clinical trials will be presented.

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“…2-imidazolines are a class of important heterocyclic compounds due to their potent biological activity and surfactant property. [10,11] Among various 2-imidazolines, hydroxy-functionalized 2-imidazoline is of particular appeal, as the extra hydroxy functional group renders it particularly useful for the synthesis of many physiologically active compounds, such as RX 781094, cirazoline and phentolamine as adrenergic antagonists [Scheme 1, (3)]. [12,13] The conventional manufacture of 2-imidazoline mainly relies on the condensation of ethylenediamine (EDA) with costly pre-functionalized fossil-based chemicals, such as nitriles and esters, which usually involve several synthetic steps from fossil fuel [Scheme 1, (1)].…”

Section: Introductionmentioning

confidence: 99%

Single‐Step Sustainable Production of Hydroxy‐Functionalized 2‐Imidazolines from Carbohydrates

Darcel

Fischmeister

2022

ChemSusChem

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Dedicated to Professor Matthias Beller, on the occasion of his 60 th birthdayManufacturing valuable N-containing chemicals from biomass is highly desirable yet challenging. Herein, a novel strategy was developed for efficient production of 2-(1-hydroxyethyl)-imidazoline (HI), a high-value and versatile building block for synthesizing a myriad of bioactive targets, directly from carbohydrates under mild reaction conditions. With this strategy, bio-based HI was produced from fructose in one step with as high as 77 C % isolated yield in the presence of ethylenedi-amine (EDA) and InCl 3 at 130 °C. The synergistic functions of EDA and InCl 3 were identified for the transformation, wherein EDA promoted the scission of CÀ C bond of fructose backbone via retro-aldol (RÀ A) reaction and rapidly trapped in-situ formed reactive carbonyl-containing C 3 intermediate for HI formation to avoid undesired side reaction, and InCl 3 facilitated the formation of this C 3 intermediate and the final 1,2-hydrid shift step.

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Imidazoline derivatives: a patent review (2006 – present)

Cited by 16 publications

References 69 publications

Electrochemical and Computational Insights on the Application of Expired Metformin Drug as a Novel Inhibitor for the Sweet Corrosion of C1018 Steel

Electrochemical and Computational Insights on the Application of Expired Metformin Drug as a Novel Inhibitor for the Sweet Corrosion of C1018 Steel

Chemical Variations on the p53 Reactivation Theme

Single‐Step Sustainable Production of Hydroxy‐Functionalized 2‐Imidazolines from Carbohydrates

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