118-58-1Relevant articles and documents
Esterification of salicylic acid using Br?nsted acidic ionic liquid based on Keggin heteropoly acid
Bamoharram, Fatemeh F.,Heravi, Majid M.,Ebrahimi, Javad,Tavakoli-Hoseini, Nilofar
, p. 36 - 42 (2014)
For the first time, a newwater stable Br?nsted acidic ionic liquid based on Keggin heteroployacid (HPA) was used as environmentally benign catalytic medium in the esterfication of salicylic acid with aliphatic alcohols, CnH2n+1OH (n = 1-5) and benzylic alcohols, RC6H4CH2OH (R = H, NO2, OCH3). This ionic liquid (IL) afforded excellent yield in both thermal conditions and microwave irradiation. Maximum yields were observed under microwave irradiation. Different reaction runs were conducted by varying the reaction parameters such as molar ratio of reactants, weight of the IL, and reaction period in order to optimize the reaction. The IL was easily recovered and reused many times. No significant loss in catalytic activity was observed on recycling.
Design, synthesis and biological evaluation of hybrid nitroxide-based non-steroidal anti-inflammatory drugs
Thomas, Komba,Moody, Terry W.,Jensen, Robert T.,Tong, Jason,Rayner, Cassie L.,Barnett, Nigel L.,Fairfull-Smith, Kathryn E.,Ridnour, Lisa A.,Wink, David A.,Bottle, Steven E.
, p. 34 - 47 (2018)
Dual-acting hybrid anti-oxidant/anti-inflammatory agents were developed employing the principle of pharmacophore hybridization. Hybrid agents were synthesized by combining stable anti-oxidant nitroxides with conventional non-steroidal anti-inflammatory drugs (NSAIDs). Several of the hybrid nitroxide-NSAID conjugates displayed promising anti-oxidant and anti-inflammatory effects on two Non-Small Cell Lung Cancer (NSCLC) cells (A549 and NCI-H1299) and in ameliorating oxidative stress induced in 661 W retinal cells. One ester-linked nitroxide-aspirin analogue (27) delivered better anti-inflammatory effects (cyclooxygenase inhibition) than the parent compound (aspirin), and also showed similar reactive oxygen scavenging activity to the anti-oxidant, Tempol. In addition, a nitroxide linked to the anti-inflammatory drug indomethacin (39) significantly ameliorated the effects of oxidative stress on 661 W retinal neurons at efficacies greater or equal to the anti-oxidant Lutein. Other examples of the hybrid conjugates displayed promising anti-cancer activity, as demonstrated by their inhibitory effects on the proliferation of A549 NSCLC cells.
A facile and efficient nucleophilic displacement reaction at room temperature in ionic liquids
Judeh, Zaher M.A,Shen, Hao-Yu,Chi, Bun Ching,Feng, Li-Chun,Selvasothi, Selvaratnam
, p. 9381 - 9384 (2002)
We have investigated the use of room temperature ionic liquids as catalytic and environmentally benign solvents for the facile homogenous synthesis of benzyl salicylate by the nucleophilic displacement reaction between sodium salicylate and benzyl chloride. The reaction was found to proceed under relatively mild conditions with excellent conversion (up to 96%) without the use of PTCs. The ionic liquids were recycled and reused. The effect of temperature was also investigated. No by-products were observed after 1H NMR and GC analysis.
Aspirination of α-aminoalcohol (sarpogrelate M1)
Park, Sunhwa,Lee, Jiyun,Shin, Kye Jung,Seo, Jae Hong
, (2016)
Aspirination of α-aminoalcohol (sarpogrelate M1) has been performed under various general esterification conditions. In most cases, the desired aspirinate ester was obtained at a low yield with unexpected byproducts, the formation of which was mostly derived from the chemical properties of the tertiary α-amino group. After systematic analysis of those methods, the aspirinated sarpogrelate M1 was prepared using a two-step approach combining salicylate ester formation and acetylation.
Homogeneous system for the synthesis of benzyl salicylate
Sivakumar, Sri,Pangarkar, Vishwas G.,Sawant, Sudhir B.
, p. 149 - 151 (2002)
Synthesis of benzyl salicylate from sodium salicylate and benzyl chloride in the absence of a PTC and with dimethyl formamide as a solvent has been reported. Almost complete conversion of benzyl chloride can be achieved in 1.5 h at 110°C. The batch time and the reaction temperature are considerably less than that for the commercial process using a PTC. Kinetics of the reaction have been investigated.
Design, synthesis, and biological evaluation of carbamate derivatives of N-salicyloyl tryptamine as multifunctional agents for the treatment of Alzheimer's disease
Liu, Dan,Zhang, Honghua,Wang, Yuying,Liu, Wencheng,Yin, Gaofeng,Wang, Degui,Li, Junfang,Shi, Tao,Wang, Zhen
, (2021/12/20)
In this study, we designed, synthesized, and evaluated a series of carbamate derivatives of N-salicyloyl tryptamine as multifunctional therapeutic agents for the treatment of Alzheimer's disease (AD). After screening the acetylcholinesterase (AChE)/butyrylcholinesterase (BChE) inhibitory activities, target compound 1g stood out as a mixed type reversible dual inhibitor of AChE and BChE. In addition, molecular docking studies were conducted to explore the actions on AChE and BChE. The results showed that 1g could decrease the level of pro-inflammatory cytokines NO, iNOS, IL-6, TNF-α, and ROS, increase the level of anti-inflammatory cytokines IL-4, and inhibit the aggregation of Aβ1-42. Moreover, the administration of 1g suppressed the activity of AChE in the brain. In a word, the compound 1g is effective for improving learning and memory behavior, blood-brain barrier permeation, pharmacokinetics, ChE inhibition, and anti-neuroinflammation. It may be considered as a promising multi-functional therapeutic agent for further investigation for the treatment of AD.
Benzoic acid tryptamine derivative as well as preparation method and application thereof
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Paragraph 0033, (2021/10/30)
The invention provides a benzoic acid tryptamine derivative as well as preparation and application thereof. The benzoic acid tryptamine derivative uses a salicylic acid compound as a starting raw material and is protected by benzyl. The method comprises the following four-step reaction synthesis of carbamylation, deprotection and condensation. The benzoic acid tryptamine derivative prepared by the invention has dual inhibition effects of acetylcholinesterase and butyrylcholine esterase. Moreover, as a hybrid reversible inhibitor, the content and expression AChE of cells and animals can be reduced. , Good anti-neuroinflammation activity can be achieved, A β aggregation can be inhibited, BACE-1 expression is reduced. The learning memory and anti-depression ability of AD model mice can be remarkably improved, no obvious toxicity exists on cells and animals, and the drug has good pharmacokinetic performance and blood brain barrier permeability, and can be applied to preparation of's disease treatment drugs.
ZWITTERIONIC CATALYSTS FOR (TRANS)ESTERIFICATION: APPLICATION IN FLUOROINDOLE-DERIVATIVES AND BIODIESEL SYNTHESIS
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Paragraph 0015; 0028, (2021/01/29)
An amide/iminium zwitterion catalyst has a catalyst pocket size that promotes transesterification and dehydrative esterification. The amide/iminium zwitterions are easily prepared by reacting aziridines with aminopyridines. The reaction can be applied a wide variety of esterification processes including the large-scale synthesis of biodiesel. The amide/iminium zwitterions allow the avoidance of strongly basic or acidic condition and avoidance of metal contamination in the products. Reactions are carried out at ambient or only modestly elevated temperatures. The amide/iminium zwitterion catalyst is easily recycled and reactions proceed in high to quantitative yields.
Amide/Iminium Zwitterionic Catalysts for (Trans)esterification: Application in Biodiesel Synthesis
Lam, Ying-Pong,Ng, Wing-Hin,Tan, Fei,Tse, Ying-Lung Steve,Wang, Xinyan,Yeung, Ying-Yeung
, p. 8083 - 8092 (2019/08/26)
A class of zwitterionic organocatalysts based on an amide anion/iminium cation charge pair has been developed. The zwitterions are easily prepared by reacting aziridines with aminopyridines. They are catalytically applicable to transesterifications and dehydrative esterifications. Mechanistic studies reveal that the amide anion and iminium cation work synergistically in activating the reaction partners, with the iminium cationic moiety interacting with the carbonyl substrates through nonclassical hydrogen bonding. The reaction can be applied to large-scale synthesis of biodiesel under mild conditions.
Epoxide as precatalyst for metal-free catalytic transesterification
Tanaka, Shinji,Nakashima, Takuya,Satou,Oono, Hiromi,Kon, Yoshihiro,Tamura, Masanori,Sato, Kazuhiko
, p. 2009 - 2013 (2019/07/03)
Transesterification of methyl esters was accelerated by an in situ-generated metal-free catalyst comprising a quaternary alkylammonium salt and an epoxide. The combination of a quaternary alkylammonium acetate and glycidol is optimal, and various esters were synthesized from methyl esters with alcohols in good to excellent yield. Analysis of the catalyst solution revealed that basic species are generated by the ring-opening reaction of epoxide.
