123-41-1Relevant articles and documents
Alendronic acid as ionic liquid: New perspective on osteosarcoma
Branco, Luís C.,Costa-Rodrigues, Jo?o,Fernandes, Maria H.,Santos, Miguel M.,Teixeira, Sónia
, (2020)
Herein the quantitative synthesis of eight new mono-and dianionic Organic Salts and Ionic Liquids (OSILs) from alendronic acid (ALN) is reported by following two distinct sustainable and straightforward methodologies, according to the type of cation. The prepared ALN-OSILs were characterized by spectroscopic techniques and their solubility in water and biological fluids was determined. An evaluation of the toxicity towards human healthy cells and also human breast, lung and bone (osteosarcoma) cell lines was performed. Globally, it was observed that the monoanionic OSILs showed lower toxicity than the corresponding dianionic structures to all cell types. The highest cytotoxic effect was observed in OSILs containing a [C2OHMIM] cation, in particular [C2OHMIM][ALN]. The latter showed an improvement in IC50 values of ca. three orders of magnitude for the lung and bone cancer cell lines as well as fibroblasts in comparison with ALN. The development of OSILs with high cytotoxicity effect towards the tested cancer cell types, and containing an anti-resorbing molecule such as ALN may represent a promising strategy for the development of new pharmacological tools to be used in those pathological conditions.
Highly efficient green synthesis of the photochromic spironaphthoxazines using an eco-friendly choline hydroxide catalyst
Vajekar, Shailesh N.,Shankarling, Ganapati S.
, p. 338 - 347 (2020)
A greener route for the synthesis of the photochromic spironaphthoxazines employing a highly efficient, biodegradable and recyclable choline hydroxide catalyst in an aqueous medium has been described. This methodology offers diverse advantages such as mild reaction conditions, short reaction time (1 h), excellent yields (up to 91%), and operational simplicity that make it a useful and attractive option for the synthesis of the spironaphthoxazines. The choline hydroxide showed excellent catalytic performance until five recycles without significant loss of activity. The structures of synthesized spironaphthoxazines were deduced by their 1H NMR spectra and melting points.
Synthesis and thermophysical properties of biocompatible cholinium-based amino acid ionic liquids
Tao, Duan-Jian,Cheng, Zheng,Chen, Feng-Feng,Li, Zhang-Min,Hu, Na,Chen, Xiang-Shu
, p. 1542 - 1548 (2013)
Nowadays the knowledge of thermodynamic properties for amino acid ionic liquids (AAILs) has been paramount for the design of many chemical processes. In this present work, a series of cholinium-based AAILs ([Ch][AA]) were synthesized by neutralization of choline hydroxide solution with five amino acids and then were characterized by 1H NMR, Fourier transform infrared (FT-IR), elemental analysis, thermogravimetry, and differential scanning calorimetry (DSC) analysis. Physico-chemical properties such as density, viscosity, refractive index, and conductivity were measured and correlated with the empirical equations in a wide temperature range. The thermal expansion coefficient values were also calculated from the acquired experimental density values. From the experimental data, it was found that the density, viscosity, and refractive index decreased while conductivity increased with the increase of temperature. The correlation results were proposed to be in good agreement with the experimental data, and optimal fitting parameters were presented. In addition, the coefficient of thermal expansion was considered to be independent of temperature in the range of (298.15 to 353.15) K.
Functional ionic liquid from biorenewable materials: synthesis and application as a catalyst in direct aldol reactions
Hu, Suqin,Jiang, Tao,Zhang, Zhaofu,Zhu, Anlian,Han, Buxing,Song, Jinliang,Xie, Ye,Li, Wenjing
, p. 5613 - 5617 (2007)
A new room temperature ionic liquid (IL) (2-hydroxyethyl)-trimethyl-ammonium (S)-2-pyrrolidinecarboxylic acid salt ([Choline][Pro]) has been synthesized from biorenewable and nontoxic raw materials (choline chloride and l(-)-proline) in a simple and relative green route. The IL has been demonstrated to be the efficient catalyst of the direct aldol reactions between ketones and aromatic aldehydes in water at room temperature. The aldol products can be obtained with good yields and the IL in aqueous phase can be separated easily and reused.
Biofriendly ionic liquids for starch plasticization: A screening approach
Colomines,Decaen,Lourdin,Leroy
, p. 90331 - 90337 (2016)
A series of cholinium cation-based bioionic liquids (BioILs) were synthetized with the aim of screening their performance as potential plasticizers of thermoplastic starch. To synthesize these BioILs, two easy and fast synthetic routes were selected: an ion exchange reaction, direct and economical, and a two-step acid-base reaction. Most of these BioILs allowed efficient plasticization of starch by film casting. The structure of the anion used significantly influences the thermo(hygro)mechanical and recrystallization behavior, making it possible to modulate the properties of the final material.
Environmentally benign synthesis of 4-aminoquinoline-2-ones using recyclable choline hydroxide
Sanap, Anita Kailas,Shankarling, Ganapati Subray
, p. 206 - 212 (2015)
Greener synthesis of 4-aminoquinoline-2-ones was achieved by intramolecular cyclization of 2-cyanophenylamide derivatives using biodegradable and recyclable choline hydroxide (ChOH). The reaction proceeds rapidly and affords the corresponding 4-aminoquinoline-2-ones with a good to excellent yield. The protocol has the advantage of easy workup, high yields, and an environmentally benign methodology compared to other reported methods. The simplicity of this method makes it an interesting alternative to other approaches.
The "neutral" hydrolysis of simple carboxylic esters in water and the rate enhancements produced by acetylcholinesterase and other carboxylic acid esterases
Wolfenden, Richard,Yuan, Yang
, p. 13821 - 13823 (2011)
Experiments at elevated temperatures permit the determination of rate constant and thermodynamic activation parameters for the neutral hydrolysis of the neurotransmitter acetylcholine in water. At 25 °C, the extrapolated rate constant for the uncatalyzed (or neutral) hydrolysis of acetylcholine is 3.9 × 10-7 s-1 at 25 °C (ΔH? = 20.0 kcal/mol; TΔS? = -6.1 kcal/mol). Acetylcholine is more susceptible to neutral and base-catalyzed hydrolysis than ethyl acetate but less susceptible to acid-catalyzed hydrolysis. For acetylcholinesterase from the electric eel, the catalytic proficiency [(kcat/K m)/kneutral] is 2 × 1016 M-1, comparable in magnitude with the catalytic proficiencies of aminohydrolases that act on peptides and nucleosides.
Greener route for the synthesis of photo- and thermochromic spiropyrans using a highly efficient, reusable, and biocompatible choline hydroxide in an aqueous medium
Pargaonkar, Jyotsna G.,Patil, Sanjay K.,Vajekar, Shailesh N.
, p. 208 - 215 (2018)
Here, we report the synthesis of photo- and thermochromic spiropyrans promoted by a highly efficient, biocompatible, and reusable choline hydroxide (ChOH) in greener solvent water. This procedure provides several advantages such as simple workup, mild reaction conditions, short reaction time, and high yields of the products. Furthermore, the ChOH could be reused at least five times without significantly losing its catalytic activity. The structures of the synthesized spiropyran derivatives were confirmed by several characterization methods such as 1H NMR, 13C NMR, and mass spectra.
Shape-selective production of zinc phosphate in aqueous and nonaqueous media using (2-hydroxyethyl) trimethylammonium hydroxide-assisted sonochemical route
Samadi-Maybodi, Abdolraouf,Nejad-Darzi, Seyed Karim Hassani
, p. 431 - 439 (2012)
Zinc phosphatemolecular sieveswere synthesized using zinc chloride, phosphoric acid and (2-hydroxyethyl) trimethylammonium hydroxide as template, respectively. Synthesized samples were characterized by XRD, SEM and FT-IR techniques. The morphology and crystal size of the samples were investigated using ultrasonic during aging process. Large particle size (7.2 × 20.4 μm) was obtained by ultrasonication. Imperfect orthorhombic particles were obtained when the sample was mixed with magnetic stirrer; meanwhile, some rod-like particles were obtained when the mixture was stirred with ultrasonic. In addition, the rod-like b-Zn3(PO4)2· 4H2O phase was prepared using ethylene glycol as co-solvent. Iranian Chemical Society 2012.
Bifunctional Ionic Liquids Derived from Biorenewable Sources as Sustainable Catalysts for Fixation of Carbon Dioxide
Saptal, Vitthal B.,Bhanage, Bhalchandra M.
, p. 1145 - 1151 (2017)
A series of highly efficient, bifunctional ionic liquids containing a quaternary alkyl ammonium cation and an amine anion were prepared from choline and amino acids, respectively. Nine ILs were synthesized, characterized, and applied as organocatalysts for the chemical fixation of carbon dioxide to form cyclic carbonates and quinazoline-2,4(1 H,3 H)-diones. A binary mixture of an IL and a co-catalysts generates deep eutectic solvents (DESs) and accelerates the rate of the cycloaddition reaction at atmospheric pressure and low temperature (70 °C). The presence of the hydroxyl functional group of choline and the free amine group of the amino acids in the ILs has a synergistic effect on the activation of the epoxide and carbon dioxide towards the cycloaddition reactions. These ILs are biodegradable and are synthesized from easily available biorenewable sources. Additionally, this catalytic method demonstrates ultimate environmental benignity because of the mild metal- and solvent-free conditions as well as the recyclability of the catalyst and co-catalyst.
