69240-56-8Relevant academic research and scientific papers
Design and synthesis of methoxyphenyl- and coumarin-based chalcone derivatives as anti-inflammatory agents by inhibition of NO production and down-regulation of NF-κB in LPS-induced RAW264.7 macrophage cells
Emam, Soha H.,Sonousi, Amr,Osman, Eman O.,Hwang, Dukhyun,Kim, Gun-Do,Hassan, Rasha A.
, (2021/01/20)
Exaggerated inflammatory responses may cause serious and debilitating diseases such as acute lung injury and rheumatoid arthritis. Two series of chalcone derivatives were prepared as anti-inflammatory agents. Methoxylated phenyl-based chalcones 2a-l and c
Computational study and synthesis of a new class of anticonvulsants with 6 Hz psychomotor seizure test activity: 2-(1,3-benzodioxol-5-yloxy)-N'-[substituted]-acetohydrazides
Kumar, Praveen,Tripathi, Laxmi
, p. 1175 - 1193 (2021/12/21)
Background: About 50 million epileptic cases worldwide and 12 million in India are re-ported. Currently, available drugs yield adequate control of seizure in 60-70% of patients and show many toxic effects. These actualities provoked the search for novel, more efficacious and safer anti-convulsants. Objective: The concatenation of 2-(1,3-benzodioxol-5-yloxy)-N'-[substituted]-acetohydrazides SA 1-10 was designed by molecular hybridization, optimized by computational study and synthesized with the objective of obtaining a prototype of potent anticonvulsant molecules especially active against partial seizures. Methods: Computational study was performed to calculate the pharmacophoric design, projection of the pharmacokinetic parameters and docking scores of the titled compounds with molecular targets of epilepsy. The anticonvulsant activity was ascertained by 6 Hz psychomotor seizure test. Minimal motor impairment showing neurotoxicity was assessed using the Rotarod test. Results: Titled compounds possessed the indispensable elements of pharmacophore and displayed good binding affinity with molecular targets of epilepsy, such as GABA (A) alpha-1 & delta receptor, glutamate receptor, Na+/H+ exchanger and GABA-aminotransferase in docking studies. The most potent compound of the concatenation was 2-(1,3-benzodioxol-5-yloxy)-N'-[4-(4-chlorophenoxy)benzylidene]-acetohydrazide SA 4, showing 100% protection at four different time points with ED50 value 146.8 mg/kg at a TPE of 1 h in mice. Conclusion: The protection shown in 6 Hz test is implicated as the compound's ability to control partial seizures. Thus, the titled compounds can be considered as potential prototype candidates for antiepileptic therapy against partial seizures.
Method for preparing diarylether compound
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Paragraph 0063-0070, (2020/06/02)
The invention relates to a method for preparing a diarylether compound. The method comprises the following steps: dispersing an aromatic heterocyclic borate compound, a nitrobenzene compound, a coppercatalyst, an alkaline compound and an additive in an organic solvent, heating and stirring, and extracting, separating and purifying the obtained reaction solution by using an organic solvent after the reaction is completed to obtain the diarylether compound. Compared with the prior art, the method has the following advantages: the efficient preparation of the diarylether compound can be realizedunder the catalysis of bivalent copper with stable properties and low price; extra protection of inert gas is not needed, and the reaction is carried out under a heating condition in the air, so environmental friendliness is achieved; and expensive catalysis and ligands are not needed in the reaction, the reaction selectivity is high, the functional group tolerance of a substrate is good, the whole reaction process is simple and easy to implement, and the method is a brand-new synthesis method of the diarylether compound.
Highly efficient heterogeneous copper-catalysed O-arylation of phenols by nitroarenes leading to diaryl ethers
Du, Yingying,Yao, Fang,Tuo, Yuxin,Cai, Mingzhong
, p. 725 - 729 (2018/01/08)
The heterogeneous O-arylation of phenols by nitroarenes was achieved in DMF at 100 °C by using an MCM-41-immobilised bidentate nitrogen copper(II) complex [MCM-41-2N-Cu(OAc)2] as catalyst, yielding a variety of unsymmetrical diaryl ethers in good to excellent yields. This heterogeneous copper catalyst can be easily prepared by a simple procedure from commercially readily available and inexpensive reagents, recovered by filtration of the reaction solution and recycled at least seven times without significant loss of activity.
Palladium-on-Carbon-Catalyzed Coupling of Nitroarenes with Phenol: Biaryl Ether Synthesis and Evidence of an Oxidative-Addition-Promoted Mechanism
Begum, Tahshina,Mondal, Manoj,Borpuzari, Manash Protim,Kar, Rahul,Gogoi, Pradip K.,Bora, Utpal
supporting information, p. 3244 - 3248 (2017/06/21)
Nucleophilic substitution in nitroarenes to form biaryl ethers is of fundamental importance in organic synthesis. Under non-catalytic conditions, this can occur if highly activated nitroarenes are used or if the nucleophile is activated by a strong stoichiometric base. We established a new method involving the use of a ligand-free palladium-on-carbon (Pd/C) catalyst for the cross-coupling of activated nitroarenes with relatively non-nucleophilic phenol derivatives, including naphthol, in the absence of harsh bases. Control experiments, hot filtration, the three-phase test, and inductively coupled plasma atomic emission spectroscopy analysis revealed that the catalysis proceeded through an usual oxidative addition step of the nitroarene to Pd/C, which resulted in the release of active palladium particles having extremely high catalytic activity. DFT calculations revealed the origin of the selectivity of the activated nitroarenes.
Augmentation of GABAergic neurotransmission by novel N-(substituted)-2-[4- (substituted)benzylidene]hydrazinecarbothioamides - A potential anticonvulsant approach
Tripathi, Laxmi,Kumar, Praveen
, p. 477 - 487 (2013/07/19)
New N-(substituted)-2-[4-(substituted)benzylidene]hydrazinecarbothioamides were designed, synthesized and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity was established in three seizure models i.e. MES, scMET and 6 Hz model. The most active compound was N-(4-methoxyphenyl)-2-[4-(4-methylphenoxy) benzylidene]hydrazinecarbothioamide PT 30 which showed 100% protection in both MES and 6 Hz test. Compound PT 30 showed protection at three different time points in 6 Hz test at a dose of 100 mg/kg. Compound 2-[4-(4-Chlorophenoxy)benzylidene]-N-cyclohexylhydrazine carbothioamide PT 4 was also found to be active in both MES and 6 Hz test. Titled compounds exhibited good binding properties with epilepsy molecular targets GABA (A) delta and GABA (A) alpha-1 receptors, in LGA based flexible docking studies. Compounds PT 30 and PT 4 were found to elevate γ-aminobutyric acid (GABA) levels in the midbrain and medulla oblongata regions of rat brain. A computational study was carried out for calculation of pharmacophore pattern and prediction of pharmacokinetic properties.
Novel 2-(2-benzylidenehydrazinyl)benzo[d]thiazole as potential antitubercular agents
Bairwa, Vinod Kumar,Telvekar, Vikas N.
, p. 244 - 247 (2013/07/28)
Molecular hybridization approach was used to synthesize substituted 2-(2-(4-aryl oxy benzylidene) hydrazinyl)benzo thiazole derivatives with 2-hydrazinobenzothiazole and 4-(alicycli/aryl/biaryl/heteroaryl oxy)benzaldehyde as new anti-TB agents. The synthesized compounds, when tested against H37Rv strains of Mtb using Resazurin Microtitre Assay (REMA) method, showed promising activity (MIC 1.35-36.50μg/mL). 6-chloro-2-(2-(4- (pyridin-4-yloxy) benzylidene) hydrazinyl) benzo[d]thiazole (10v) gave MIC of 1.35 μg/mL. Thus making it, a potential lead could be developed for further antitubercular studies.
First palladium-catalyzed denitrated coupling reaction of nitroarenes with phenols
Wang, Hailei,Yu, Ajuan,Cao, Aijuan,Chang, Junbiao,Wu, Yangjie
, p. 611 - 614 (2013/10/21)
The first palladium-catalyzed protocol for the denitrated coupling reaction of nitroarenes with phenols has been developed, achieving unsymmetrical diaryl ethers in moderate to excellent yields. The cyclopalladated ferrocenylimine (catalyst Ic) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol%) and short reaction time (2 h). The efficiency of this reaction was demonstrated by its compatibility with a range of groups. Moreover, the rigorous exclusion of air or moisture was not required in these transformations. Copyright
A 2,2′-bipyridine-palladacycle catalyzed the coupling of arylboronic acids with nitroarenes
Peng, Dongpo,Yu, Ajuan,Wang, Hailei,Wu, Yangjie,Chang, Junbiao
, p. 6884 - 6889 (2013/07/26)
A novel palladium-catalyzed protocol for the synthesis of diaryl ethers derivatives has been developed. In the presence of 2,2′-bipyridine- cyclopalladated ferrocenylimine complex (Cat. Ic), diaryl ethers were selectively generated by adjusting reaction parameters through the coupling of arylboronic acids and nitroarenes with yields ranging from poor to good. The efficiency of this reaction was demonstrated by its compatibility with a range of groups. Moreover, the rigorous exclusion of air or moisture was not required in these transformations.
Design, synthesis, and anticonvulsant evaluation of some novel 1, 3 benzothiazol-2-yl hydrazones/acetohydrazones
Kumar, Praveen,Shrivastava, Birendra,Pandeya, Surendra N.,Tripathi, Laxmi,Stables, James P.
, p. 2428 - 2442 (2012/10/30)
A series of 2-[2-(substituted)hydrazinyl]-1,3-benzothiazole and 2-(1,3-benzothiazol-2-ylsulfanyl)-N′-(substituted)acetohydrazide were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity of the titled compounds was assessed using the 6 Hz psychomotor seizure test. The most active compound of the series was 2-(1,3-benzothiazol-2-ylsulfanyl)-N′-[4-(4-bromophenoxy)benzylidene] acetohydrazide BT 15, which showed 75% protection (3/4, 1.0 h) and 50% protection (2/4, 0.5 h) at a dose of 100 mg/kg in mice. A computational study was carried out for calculation of pharmacophore pattern and prediction of pharmacokinetic properties. Titled compounds have also exhibited good binding properties with epilepsy molecular targets such as GABA (A) alpha-1, glutamate, GABA (A) delta receptors and Na/H exchanger, in Lamarckian genetic algorithmbased flexible docking studies. Springer Science+Business Media, LLC 2011.
