6333-08-0Relevant academic research and scientific papers
Pyrazoles and pyrazolines as anti-inflammatory agents
Hadjipavlou-Litina, Dimitra,Mantzanidou, Martha,Pontiki, Eleni
, (2021/06/21)
The five-membered heterocyclic group of pyrazoles/pyrazolines plays important role in drug discovery. Pyrazoles and pyrazolines present a wide range of biological activities. The synthesis of the pyrazolines and pyrazole derivatives was accomplished via t
A simple iron-catalyst for alkenylation of ketones using primary alcohols
Sk, Motahar,Kumar, Ashish,Das, Jagadish,Banerjee, Debasis
, (2020/04/10)
Herein, we developed a simple iron-catalyzed system for the α-alkenylation of ketones using primary alcohols. Such acceptor-less dehydrogenative coupling (ADC) of alcohols resulted in the synthesis of a series of important α,β-unsaturated functionalized ketones, having aryl, heteroaryl, alkyl, nitro, nitrile and trifluoro-methyl, as well as halogen moieties, with excellent yields and selectivity. Initial mechanistic studies, including deuterium labeling experiments, determination of rate and order of the reaction, and quantitative determination of H2 gas, were performed. The overall transformations produce water and dihydrogen as byproducts.
Basic Anion-Exchange Resin-Catalyzed Aldol Condensation of Aromatic Ketones with Aldehydes in Continuous Flow
Laroche, Benjamin,Saito, Yuki,Ishitani, Haruro,Kobayashi, Shū
supporting information, p. 961 - 967 (2019/05/02)
A general method for the aldol condensation of aromatic ketones with aldehydes was developed under continuous-flow conditions using a commercially available, strongly basic anion-exchange resin (A26) as catalyst. This procedure, in addition to exhibiting a wide substrate scope, promoted carbon-carbon bond formation under mild conditions using a quasi-stoichiometric ratio of starting reagents with good to excellent yields, thereby forming a limited amount of waste and allowing the process to be applied to sequential-flow systems. A proof of concept was developed in the first fully heterogeneously catalyzed two-step flow synthesis of donepezil, which is a blockbuster commercial anti-Alzheimer's drug.
Naphthalene-triazolopyrimidine hybrid compounds as potential multifunctional anti-Alzheimer's agents
Umar, Tarana,Gusain, Siddharth,Raza, Md Kausar,Shalini, Shruti,Kumar, Jitendra,Tiwari, Manisha,Hoda, Nasimul
, p. 3156 - 3166 (2019/06/08)
In an attempt to construct potential anti-Alzheimer's agents Naphthalene-triazolopyrimidine hybrids were synthesized and screened in vitro against the two cholinesterases (ChE)s, amyloid β aggregation and for antioxidation activity. Single-crystal X-ray c
New hybrid bromopyridine-chalcones as in vivo phase II enzyme inducers: potential chemopreventive agents
Cabrera, Mauricio,Cerecetto, Hugo,González, Mercedes
, p. 2395 - 2409 (2016/12/18)
Cancer prevention can be achieved by the administration of cancer chemopreventive agents (CCAs) that prevent, delay or reverse the carcinogenic process. CCAs that are able to induce detoxification enzymes, especially monofunctional phase II enzymes, have become an excellent therapeutic strategy. Herein, we report the synthesis of eighteen new potential CCAs, structurally designed to combine (naphtho)chalcone and (bromo)pyridine skeletons. After a selection process involving in vitro phase II induction studies, cytotoxicity against tumoral cells, mutagenicity (the Ames test), and capability for DNA strand breakage (the alkaline comet assay), compound 22, (E)-3-(2-bromopyridin-3-yl)-1-(2-hydroxyphenyl)-2-propen-1-one, was selected for animal studies. The in vivo proof of concept study for derivative 22 demonstrated that it was able to significantly increase the QR and GST activities in the liver, colon and mammary gland without significant induction of the phase I enzyme, CYP. Additionally, we found that for 22 and another in vitro QR activity inducer, (E)-1-(2-hydroxyphenyl)-3-(naphthalen-1-yl)-2-propen-1-one (compound 8), Nrf2 nuclear translocation is operative allowing the exertion of protective effects via the expression of downstream phase II enzymes.
A new solid acid catalyst FeCl3/bentonite for aldol condensation under solvent-free condition
Muthuvel,Dineshkumar,Thirumurthy,Rajasri,Thirunarayanan
, p. 252 - 260 (2017/01/18)
For the first time, a new solid acid catalyst has been used for the synthesis of aryl chalcones under solvent free conditions. A simple method (solid dispersion method) has been adopted for the synthesis of FeCl3/bentonite. The prepared catalyst has been characterized by different characterization techniques. A series of E-1-(substituted phenyl)-3-(1-pyrenyl)-2-propen-1-ones have been synthesized using FeCl3/bentonite under microwave-assisted solvent-free conditions. The yields are in the range from 80 to 88%. All the synthesized chalcones have been characterized by their physical constants, analytical, IR, 1H and 13C NMR spectral data. This catalyst can be reused for further runs (after fifth cycle) without decrease in activity. This catalyst gives excellent yields and is inexpensive and easily recyclable for this reaction.
Enantioselective Diels-Alder Reactions of Cyclohexa-1,3-diene and Chalcones Catalyzed by Intramolecular Silicon-Sulfur Lewis Pairs as Chiral Lewis Acids
Shaykhutdinova, Polina,Oestreich, Martin
supporting information, p. 2768 - 2771 (2016/09/04)
The stereoselective preparation of diastereomeric dihydrosilepine-derived silicon cations decorated with another binaphthyl unit at the silicon atom is described. A sulfide donor attached to that additional binaphthyl substituent forms an intramolecular Lewis pair with the electron-deficient silicon atom, as verified by 29Si NMR spectroscopy. Both chiral sulfur-stabilized silicon cations act as catalysts in the difficult Diels-Alder reaction of cyclohexa-1,3-diene and chalcone derivatives. Both Lewis acids induce enantioselectivity, but the S,S relative configuration is superior to the S,R configuration. With the former diastereomer, enantiomeric excesses of close to 60% are obtained. These values are the highest achieved to date in this seemingly trivial cycloaddition.
Organoselenium-catalyzed baeyer-villiger oxidation of α,β-unsaturated ketones by hydrogen peroxide to access vinyl esters
Zhang, Xu,Ye, Jianqing,Yu, Lei,Shi, Xinkang,Zhang, Ming,Xu, Qing,Lautens, Mark
supporting information, p. 955 - 960 (2015/03/30)
By carefully screening the organoselenium pre-catalysts and optimizing the reaction conditions, simple dibenzyl diselenide was found to be the best pre-catalyst for Baeyer-Villiger oxidation of (E)-α,β-unsaturated ketones with the green oxidant hydrogen peroxide at room temperature. The organoselenium catalyst used in this reaction could be recycled and reused several times. This new method was suitable not only for methyl unsaturated ketones, but also for alkyl and aryl unsaturated ketones. Therefore, it provided a direct, mild, practical, highly functional group-tolerant process for the chemoselective preparation of the versatile (E)-vinyl esters from the readily available (E)-α,β-unsaturated ketones. A possible mechanism was also proposed to rationalize the activity of the organoselenium catalyst in the presence of hydrogen peroxide in this Baeyer-Villiger oxidation reaction.
Oxygen as single oxidant for two steps: Base-free one-pot Pd(ii)-catalyzed alcohol oxidation & arylation to halogen-intact β-aryl α,β-enones
Vellakkaran, Mari,Andappan, Murugaiah M. S.,Nagaiah, Kommu
, p. 45490 - 45494 (2014/12/10)
Using oxygen as the sole oxidant for two steps, we developed a new method to synthesize β-aryl α,β-enones by fine-tuning the Pd(ii)-catalyzed oxidation of allyl alcohol to subsequent arylation with arylboronic acids, arylboronic ester and aryltrifluoroborate salt. This one-pot green method does not require copper salt, base, and intermediate isolation. Halogen-bearing chalcones, dibenzylideneacetones and arylalkyl enones were synthesized in good yields. This journal is
Solvent-free synthesis, spectral correlations and antimicrobial activities of some aryl e 2-propen-1-ones
Sathiyamoorthi,Mala,Sakthinathan,Kamalakkannan,Suresh,Vanangamudi,Thirunarayanan
, p. 245 - 256 (2013/11/06)
Totally 38 aryl E 2-propen-1-ones including nine substituted styryl 4-iodophenyl ketones have been synthesised using solvent-free SiO 2-H3PO4 catalyzed Aldol condensation between respective methyl ketones and substituted benzaldehydes under microwave irradiation. The yields of the ketones are more than 80%. The synthesised chalcones were characterized by their analytical, physical and spectroscopic data. The spectral frequencies of synthesised substituted styryl 4-iodophenyl ketones have been correlated with Hammett substituent constants, F and R parameters using single and multi-linear regression analysis. The antimicrobial activities of 4-iodophenyl chalcones have been studied using Bauer-Kirby method.
