- Functionalized imidazolium-based ionic liquids: biological activity evaluation, toxicity screening, spectroscopic, and molecular docking studies
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A series of long-chain imidazolium-based ionic liquids (ILs) 1-dodecyl-3-methylimidazolium chloride (1), 1,3-bis(octyloxycarbonylmethyl)imidazolium chloride (2) and 1-dodecyloxycarbonylmethyl-3-methyloxycarbonylmethylimidazolium chloride (3), were synthesized and evaluated as antimicrobials against a wide range of bacteria and fungi. Toxicological risks of selected compounds were assessed using the biomodels of various organizational and functional levels. All compounds demonstrated significant antibacterial and antifungal activity. The toxicity results indicate that ILs containing an ester functional group in the alkyl side chain exhibited much lower toxicity to D. magna and acetylcholinesterase inhibition than ILs with long alkyl chain without polar substituents, while toxicity toward Danio rerio was on a par. The HSA-binding properties of ILs have been investigated by FT-IR spectroscopy technique and the evidences have suggested that the test compounds could induce the protein unfolding and changes in the secondary structure of HSA. The docking studies were carried out to provide structural insights of the ILs–HSA-binding interactions. The docked compounds exhibit a high binding affinity to HSA and the hydrogen bonding, hydrophobic and electrostatic interactions played a major role in the process. ILs 2 and 3 may be perspective for further investigation as potential low-toxic biocides with high antimicrobial activity against reference and clinical multidrug-resistant strains.
- Trush, Maria M.,Semenyuta, Ivan V.,Hodyna, Diana,Ocheretniuk, Alla D.,Vdovenko, Sergey I.,Rogalsky, Sergiy P.,Kalashnikova, Larisa E.,Blagodatnyi, Volodymyr,Kobzar, Oleksandr L.,Metelytsia, Larisa O.
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- Synthesis and physico-chemical properties of ionic liquids—3-methyl-1-alkyloxycarbonylmethylpyridinium hexafluorophosphates
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Ionic liquids based on 1-alkyloxycarbonylmethyl-3-methylpyridinium and Cl– and PF6 – anions have been synthesized. The conductivity of their solutions in acetonitrile and the thermal stability over 25–500°C in air have been determined.
- Zhuravlev,Voronchikhina
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- Cyanine type modified compound Intermediate and preparation method and application thereof
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The invention provides a cyanine type modified compound with the structure of the formula (I), and also provides a preparation method of the cyanine type modified compound. The Vinamidinium-salt new synthetic route is developed, the process parameters are optimized, the yield of the intermediate is improved, the product quality is also good, and the effect of increasing the yield of the next step is crucial. In addition, since the cyanine-based modified compound contains more double bonds and strong electron-withdrawing groups, it can be used as an ultraviolet - blue light absorbent.
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Paragraph 0037; 0040-0042
(2021/11/03)
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- New Diesters Derived from Piperine: In silico Study and Evaluation of Their Antimicrobial Potential
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Piperine, previously extracted from black pepper (Piper nigrum L.), was used as a precursor for the synthesis of twelve new diester derivatives. The final products were obtained through the bimolecular nucleophilic substitution reaction (SN2) of the alkyl 2-chloroacetates and the salt of piperic acid, obtained from the basic hydrolysis of piperine. The compounds were synthesized with yields of 55-84% and characterized by infrared spectroscopy and 1H and 13C nuclear magnetic resonance. The evaluation of the compounds’ potential as new drug candidates was done through an in silico study of ADME properties (absorption, distribution, metabolization and excretion) and evaluation of antimicrobial activity against bacterial strains (Staphylococcus aureus and Pseudomonas aeruginosa), yeasts (Candida albicans and Candida tropicalis) and filamentous fungi (Aspergillus fumigatus, Aspergillus flavus and Aspergillus niger). The in silico study showed that the compounds were good drug candidates and antimicrobial evaluation demonstrated that 9 of the 12 compounds exhibited a minimum inhibitory concentration (MIC) ranging 1024-256 μg mL?1
- Barbosa-Filho, José M.,Brand?o, Maria Cláudia R.,Lima, Edeltrudes O.,Lira, Bruno F.,Neto, Hermes D.,Souza, Helivaldo D. S.,Trindade, Emmely O.,de Athayde-Filho, Petr?nio F.
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p. 1668 - 1678
(2020/10/09)
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- Preparation method of novel thermosensitive ionic liquid and method for synthesizing chloracetate catalytically
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The invention discloses an acid functionalized-temperature controlled ternary heteropolyacid ionic liquid and a preparation method thereof, as well as an esterification method for synthesizing chloracetate catalytically. The structural formula of the heteropolyacid ionic liquid is as shown in a formula (I). The ionic liquid has a temperature responding characteristic during esterification reactionof chloroacetic acid and chloroacetic acid, is mixed with a reactant as one phase at the reaction temperature, and is further divided into two phases with the product when the temperature is reducedto a room temperature after the reaction. A catalyst and a reaction product can be separated quickly by simple filtration. The ionic liquid not only has the advantages of being convenient to recover and free of waste acid emission, but also has the characteristics of being high in esterification efficiency, good in repeated using performance and the like.
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Paragraph 0027
(2019/04/02)
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- Synthesis and evaluation of novel cationic gemini surfactants based on Guava crude fat as petroleum-collecting and dispersing agents
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Cationic gemini surfactants based on Guava fat mixed fatty alcohols and isolated fatty alcohols C8, C12, C16, C18 were synthesized. The surface properties and thermodynamic parameters of micellization process, of the new cationic gemini surfactants have been investigated. Furthermore, the petroleum-collecting and dispersing indices of obtained surfactants, in waters of varying salinity have been studied. The results revealed that the tendency of these surfactants toward adsorption process was more than its tendency micellization and show high petroleum-collecting and dispersing properties.
- Abo-Riya, Mohammed,Tantawy, Ahmed H.,El-Dougdoug, Wagdy
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p. 642 - 650
(2016/07/06)
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- Esterifications of carboxylic acids and alcohols catalyzed by Al 2(SO4)3 · 18H2O under solvent-free condition
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Esterifications of equimolar mixture of carboxylic acids and alcohols can be effectively catalyzed by Al2(SO4)3 · 18H2O under solvent-free condition. The esterification catalyzed by Al2(SO4)3 · 18H2O is a promising green method thanks to no need of organic solvent, no pollution, no causticity and ease to handle after reaction. This catalyst is of a low toxicity (usually it is used as purifying agent for drinking water), low-cost compound and is easily separated from the reaction mixture by simple filtration. Moreover, the catalyst can be recycled for the further esterification and the conversion does not evidently decrease.
- Gang, Li,Wenhui, Pang
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experimental part
p. 559 - 565
(2011/01/07)
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- Mild and practical acylation of alcohols with esters or acetic anhydride under distannoxane catalysis
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Distannoxane catalysts effect acylation of alcohols by action of esters and acetic anhydride. In particular, use of enol esters provides an extremely useful method. Primary alcohols are acylated in preference to secondary ones as well as phenol. Both acid- and base-sensitive functional groups remain intact. Especially unique is the discrimination of thio function which is completely tolerant under the present reaction conditions. This method is highly practical since operation is quite simple. Esters and solvents can be used without purification and no inert atmosphere is necessary. The products can be isolated simply by column chromatography or distillation without aqueous workup.
- Orita, Akihiro,Sakamoto, Katsumasa,Hamada, Yuji,Mitsutome, Akihiro,Otera, Junzo
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p. 2899 - 2910
(2007/10/03)
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- Catalytic esterification of alcohols, carboxylic acids and transesterification reactions with cerium(IV) triflate
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Esterification reactions of alcohols with acetic, chloroacetic, trifluoroacetic, propionic, stearic, and benzoic acids were catalyzed with Ce(OTf)4 in a solvent or under solvent-free conditions with high yields. The formylation and acetylation of primary and secondary alcohols were also easily achieved in ethyl formate and ethyl acetate. A high retention of the configuration was observed in the acetylation and formylation of (-)-menthol.
- Iranpoor, Nasser,Shekarriz, Marzieh
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p. 455 - 458
(2007/10/03)
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- Acylation of alcohols and amines with vinyl acetates catalyzed by Cp*2Sm(thf)2
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Cp*2Sm(thf)2 was found to be an efficient catalyst for the acylation of alcohols and amines with esters under mild conditions. In the present acylation, vinyl and isopropenyl acetates served as good acylating agents. Thus, a variety of alcohols and amines underwent acylation with vinyl and isopropenyl acetates in the presence of Cp*2Sm(thf)2 to give the corresponding esters and amides in good to excellent yields. This catalytic acylation of alcohols and amines offers an additional useful method by the use of various esters, instead of acid anhydrides and acid chlorides, as acylating agents under very mild conditions.
- Ishii, Yasutaka,Takeno, Mitsuhiro,Kawasaki, Yumi,Muromachi, Akifumi,Nishiyama, Yutaka,Sakaguchi, Satoshi
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p. 3088 - 3092
(2007/10/03)
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- A study of modified betaines as cryoprotective additives
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Glycinebetaine and N-modified betaines have been previously shown to be effective at reducing leakage from liposomes on freeze-thaw procedures. This study involved the preparation of a series of other modified betaines and the comparison of their abilities to reduce leakage from frozen multilamellar liposomes. All the compounds investigated, with the exception of the octyl ester of betaine, reduced the degree of leakage on freezing and thawing with additive concentrations up to 0.6 M. The betaine esters were less effective than betaine as cryoprotective additives and caused an increase in the leakage from unfrozen liposomes. Taurinebetaine, a sulphobetaine, was also less effective at reducing leakage on freezing than betaine and again increased leakage from unfrozen liposomes. Increasing the number of methylene groups between the carboxylate group and the nitrogen improved the ability to reduce leakage, particularly at lower additive concentrations.
- Lloyd,Olliff,Rutt
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p. 704 - 707
(2007/10/02)
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- Micellar properties of sodium alkyl sulfoacetates and sodium dialkyl sulfosuccinates in water
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Viscosity, conductivity, density, and fluorescence quenching studies were conducted in aqueous micellar solutions at 25.0 deg C of sodium alkyl sulfoacetates and sodium dialkyl sulfosuccinates in a comparison of one-tailed and two-tailed surfactant systems.The hexyl, octyl, and decyl members of the former group and the dihexyl and dioctyl members of the latter group were investigated.The results indicated that the sulfoacetates most likely form spherical micelles with aggregation numbers 20 for hexyl, 42 for octyl, and 70 for decyl with three methods for size determination giving concordant results.For the sulfosuccinates, the aggregation numbers from fluorescence quenching were 38 for the dihexyl and 56 for the dioctyl in agreement with the results from the conductance technique which means that spherical micelles are likely formed also.Volume changes on micellization were obtained for the sulfoacetates.
- Jobe, David J.,Reinsborough, Vincent C.
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p. 280 - 284
(2007/10/02)
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- Alkyl alkanoate derivatives of substituted piperazine-diones and polymer compositions stabilized thereby
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Alkyl alkanoate derivatives of substituted piperazinediones are stabilizers for synthetic polymeric materials normally subject to deterioration caused by ultraviolet light. The compounds may be formed by reacting a substituted piperazinedione with an acrylate or a crotonate, or reacting the alkali or alkaline earth salt of a substituted piperazine dione with a haloalkanoate. Polymeric compositions containing these stabilizers may also contain a hindered phenolic compound. A typical embodiment is n-octadecyl-β-(15{7,15-diazadispiro[5,1,5,3]hexadecane-14,16-dione}propionate.
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