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2941-78-8Relevant academic research and scientific papers
Discovery of Novel Tacrine-Pyrimidone Hybrids as Potent Dual AChE/GSK-3 Inhibitors for the Treatment of Alzheimer's Disease
Yao, Hong,Uras, Giuseppe,Zhang, Pengfei,Xu, Shengtao,Yin, Ying,Liu, Jie,Qin, Shuai,Li, Xinuo,Allen, Stephanie,Bai, Renren,Gong, Qi,Zhang, Haiyan,Zhu, Zheying,Xu, Jinyi
, p. 7483 - 7506 (2021/06/28)
Based on a multitarget strategy, a series of novel tacrine-pyrimidone hybrids were identified for the potential treatment of Alzheimer's disease (AD). Biological evaluation results demonstrated that these hybrids exhibited significant inhibitory activities toward acetylcholinesterase (AChE) and glycogen synthase kinase 3 (GSK-3). The optimal compound 27g possessed excellent dual AChE/GSK-3 inhibition both in terms of potency and equilibrium (AChE: IC50 = 51.1 nM; GSK-3β: IC50 = 89.3 nM) and displayed significant amelioration on cognitive deficits in scopolamine-induced amnesia mice and efficient reduction against phosphorylation of tau protein on Ser-199 and Ser-396 sites in glyceraldehyde (GA)-stimulated differentiated SH-SY5Y cells. Furthermore, compound 27g exhibited eligible pharmacokinetic properties, good kinase selectivity, and moderate neuroprotection against GA-induced reduction in cell viability and neurite damage in SH-SY5Y-derived neurons. The multifunctional profiles of compound 27g suggest that it deserves further investigation as a promising lead for the prospective treatment of AD.
Br?nsted Acid-Catalyzed Asymmetric Ring-Closing Alkylation of Inert N-substituted Pyrroles with α, β-Unsaturated Ketones
Wei, Zhao,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
supporting information, p. 3694 - 3697 (2019/07/12)
A Chiral Br?nsted acid catalyzed asymmetric intramolecular ring-closing alkylation of inert pyrroles with α, β-unsaturated ketones has been developed. This approach gave a wide range of 4-phenyl-4,5-dihydro-6H-benzo[f]pyrrolo[1,2-a]azepin-6-ones in high yields with good enantioselectivities under mild reaction conditions. (Figure presented.).
Synthetic method of 2-amino-4-bromo-N,5-dimethyl benzamide
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Paragraph 0005; 0006; 0007, (2017/04/27)
The invention discloses a synthetic method of 2-amino-4-bromo-N,5-dimethyl benzamide, and belongs to the field of chemical synthesis. The synthetic method comprises the following steps: firstly, by taking 2-nitro-5-methyl benzoic acid as a raw material and using ferric chloride hexahydrate and palladium as a composite catalyst, adding the materials into hydrazine hydrate solution and performing reduction reaction to obtain 2-amino-5-methyl benzoic acid; adding the 2-amino-5-methyl benzoic acid and dichloromethane into bis(trichloromethyl) carbonate tetrahydrofuran solution by taking pyridine as a catalyst, and performing cyclization reaction; after the reaction is ended, performing microwave heating to reflux; after reflux, adding methylamine water solution and performing amination reaction to obtain 2-amino-N,5-dimethyl benzamide; finally, enabling the 2-amino-N,5-dimethyl formamide, hydrogen peroxide and hydrobromic acid solution to perform halogenating reaction, thus obtaining the 2-amino-4-bromo-N,5-dimethyl benzamide.
Gas-phase domino cyclization of phosphonium ylides leading to the total synthesis of Eustifoline D
Aitken, R. Alan,Murray, Lorna
supporting information, p. 4328 - 4332 (2017/10/17)
Six stabilised phosphonium ylides bearing ortho-benzylaminophenyl and cinnamoyl (or a heterocyclic analogue) groups have been prepared and upon flash vacuum pyrolysis at 800 °C were found to undergo cascade cyclization processes to give mainly 3-styrylquinolines but also in some cases ring-fused carbazoles and other fused-ring heterocyclic products. By starting with an appropriate ring-methylated precursor the natural product Eustifoline D was obtained in 19% yield in the pyrolysis in addition to the 3-(2-furylethenyl)quinoline (46%).
The Synthesis of 5-Amino-dihydrobenzo[b]oxepines and 5-Amino-dihydrobenzo[b]azepines via Ichikawa Rearrangement and Ring-Closing Metathesis
Chwastek, Monika,Pieczykolan, Micha?,Stecko, Sebastian
, p. 9046 - 9074 (2016/10/17)
The combination of Ichikawa's rearrangement and a ring-closing metathesis reaction of allyl carbamates is presented as a method for the preparation of 5-amino-substituted 2,5-dihydro-benzo[b]oxepines, 2,5-dihydro-benzo[b]azepines, and 2,5-dihydro-benzo[b]thiepins. It was demonstrated that the use of nonracemic allyl carbamates enables the synthesis of enantioenriched benzo-fused seven-membered heterocycles. Finally, it was shown that further functionalization of the obtained structures allows access to pharmacologically active 5-amino-substituted 2,3,4,5-tetrahydro-1-benzo[b]oxepine scaffolds.
Catalysis and mechanistic studies of ruthenium and osmium on synthesis of anthranilic acids
Karthikeyan,Jagadeesh, Rajenahally V.,Sree Sandhya,Puttaswamy,Nithya,Kumar, S. Senthil,Bhagat
experimental part, p. 34 - 46 (2011/09/16)
Ruthenium, osmium and ruthenium + osmium catalyzed synthetic methodology was developed for the synthesis of anthranilic acids from indoles in good to excellent yields using bromamine-B in alkaline acetonitrile-water (1:1) at 313 K. Detailed catalysis studies of ruthenium, osmium and the mixture of both were carried out for the synthetic reactions. The positive synergistic catalytic activity of Ru(III) + Os(VIII) was observed to a large extent with the activity greater than the sum of their separate catalytic activities. Detailed kinetic and mechanistic investigations for each catalyzed reactions were carried out. The kinetic pattern and mechanistic picture of each catalyzed reaction were found to be different for each catalyst and to obey the underlying rate laws: rate = k[BAB]t[Indole][Ru(III)]x[OH-] y rate = k[BAB]t[Indole][Os(VIII)][OH-] y rate = k[BAB]t[Indole]o[Ru(III) + Os(VIII)][OH-]y where, x, y Os(VIII) > Ru(III). This trend may be attributed to the different d-electronic configuration of the catalysts. The proposed mechanisms and the rigorous kinetic models derived give results that fit well with the experimental data in each catalyzed reaction. Copyright
Bromamine-B/PdCl2 is an efficient system for the synthesis of anthranilic acids from indoles and indigos
Kumar, C. Vinod,Shivananda,Raju, C. Nagu,Jagadeesh
experimental part, p. 3480 - 3487 (2011/02/22)
A convenient method has been developed for the conversion of indoles and indigos into anthranilic acids in good to excellent yields using a bromamine-B/PdCl2 system. The general process utilizes our efficient method for the oxidation of indoles and indigos in alkaline (pH 12) acetonitrile/water (1:1) at 60°C. Copyright Taylor & Francis Group, LLC.
Synthesis of new 1,2,3-triazolo[1,5-a]quinazolinones
Pokhodylo, Nazariy T.,Matiychuk, Vasyl S.
scheme or table, p. 415 - 420 (2010/06/16)
(Chemical Equation Presented) Synthesis of novel 3-substituted-1,2,3- triazolo[1,5-a]quinazolinones in high yields was performed via anionic hetero-domino reaction of appropriate substituted 2-azidobenzoates prepared from isatines and acetonitriles activated by 1,3-thiazole, 1,3-benzothiazole, 1,3,4-oxadiazole, and 1,2,4-oxadiazole rings. It was shown that acetonitriles exhibited high reactivity and were convenient methylenic compounds for such reactions providing rapid structural variation.
An efficient selective reduction of aromatic azides to amines employing BF3·OEt2/NaI: Synthesis of pyrrolobenzodiazepines
Kamal, Ahmed,Shankaraiah,Markandeya,Reddy, Ch. Sanjeeva
experimental part, p. 1297 - 1300 (2009/04/06)
A selective and facile method for the reduction of aromatic azides to amines by employing borontrifluoride diethyl etherate and sodium iodide. This methodology has been applied towards the preparation of biologically important imine-containing pyrrolobenzodiazepines and their dilactams through intramolecular reductive-cyclization process. In this protocol the reagent systems are amenable for the generation of solution-phase combinatorial synthesis. Georg Thieme Verlag Stuttgart.
TUMOR NECROSIS FACTOR ALPHA INHIBITORS AND THEIR USE IN THE TREATMENT OF HUMAN DISEASES
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Page/Page column 41, (2008/12/06)
treatment of a variety of disorders, including the treatment of pathological conditions associated with tumor necrosis factor alpha. The inhibitors of tumor necrosis factor alpha have the following structures: including stereoisomers, pharmaceutically acceptable salts, and solvates thereof, wherein substituents are as defined herein. Compositions containing an inhibitor of tumor necrosis factor alpha in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.
