22042-71-3Relevant articles and documents
Three-component synthesis of chromeno β-lactam hybrids for inflammation and cancer screening
Borazjani, Nassim,Sepehri, Saghi,Behzadi, Maryam,Jarrahpour, Aliasghar,Rad, Javad Ameri,Sasanipour, Maryam,Mohkam, Milad,Ghasemi, Younes,Akbarizadeh, Amin Reza,Digiorgio, Carole,Brunel, Jean Michel,Ghanbari, Mohammad Mehdi,Batta, Gyula,Turos, Edward
, p. 389 - 403 (2019)
Highly diastereoselective synthesis of chromeno β-lactam hybrids was achieved by an efficient one-pot three-component reaction. With this procedure, the desired β-lactam products were obtained in good yields and with exclusive cis stereoselection, by combining a variety of benzaldehydes, malononitrile, and either 5,5-dimethylcyclohexane-1,3-dione or 4-hydroxycoumarin in the presence of 1,4-diazabicyclo [2.2.2]octane under reflux conditions. These adducts were structurally characterized on the basis of IR, 1D and 2D NMR spectra, X-ray analysis, H–H COSY and H–C HSQC two-dimensional NMR experiments, and elemental analysis. Each of the synthesized compounds was screened for anti-inflammatory and anticancer activities. β-Lactams 5b and 8b showed a 53.4 and 19.8 anti-inflammatory ratio, respectively, and 5b appeared more active than the well-known dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation. β-Lactams 5a, 5b, 5e, 5f, 5g, 8c, 8j and 8p also showed good antitumor activity against the SW1116 (colon cancer) cell line without notable cytotoxicity towards the HepG2 control cell line.
Methyl 2-(2-(4-formylphenoxy)acetamido)-2-substituted acetate derivatives: A new class of acetylcholinesterase inhibitors
Wen, Huan,Zhou, Yayao,Lin, Chonglan,Ge, Hui,Ma, Lin,Wang, Zihou,Peng, Wenlie,Song, Huacan
, p. 2123 - 2125 (2007)
A new class of inhibitors of acetylcholinesterase (methyl 2-(2-(4-formylphenoxy)acetamido)-2-substituted acetate derivatives) is described. Compounds 4b and 4i were found to be more potent than galanthamine in inhibiting acetylcholinesterase.
Synthesis, structural characterization, and antibacterial activity of tricyclohexyltin aryloxyacetates
Zhang, Hao,Yu, Haixia,Liu, Xijie,Tian, Laijin
, p. 157 - 164 (2015)
Three tricyclohexyltin aryloxyacetates, p-YC6H4OCH2COOSn(C6H11-c)3 (where Y=H, 1; CHO, 2; CH2OH, 3), have been synthesized and characterized by means of elemental analysis, IR, and NMR (1H, 13C, and 119Sn) spectroscopy. The crystal structures of complexes 1 and 3 are determined by X-ray single-crystal diffraction. The carboxylate in the compounds is monodentate. The tin atom of compound 1 adopts distorted tetrahedral coordination geometry. In the crystal lattice of compound 3, there is a four-coordinated tin and a five-coordinated tin in which the fifth coordination site is occupied by a water molecule, and the molecules are linked by R33(30) and R55(28) hydrogen bonds into a two-dimensional supramolecular network. Bioassay results have shown that the compounds have good in vitro antibacterial activity against Escherichia coli.
Discovery of Novel Dual-Target Inhibitor of Bromodomain-Containing Protein 4/Casein Kinase 2 Inducing Apoptosis and Autophagy-Associated Cell Death for Triple-Negative Breast Cancer Therapy
Chen, Juncheng,Chiang, Cheng-Ming,He, Gu,Liu, Bo,Liu, Jie,Ouyang, Liang,Tang, Pan,Wang, Guan,Yang, Chengcan,Ye, Tinghong,Zhang, Jifa,Zhang, Jin,Zou, Ling
, p. 18025 - 18053 (2022/01/03)
Bromodomain-containing protein 4 (BRD4) is an attractive epigenetic target in human cancers. Inhibiting the phosphorylation of BRD4 by casein kinase 2 (CK2) is a potential strategy to overcome drug resistance in cancer therapy. The present study describes the synthesis of multiple BRD4–CK2 dual inhibitors based on rational drug design, structure–activity relationship, and in vitro and in vivo evaluations, and 44e was identified to possess potent and balanced activities against BRD4 (IC50 = 180 nM) and CK2 (IC50 = 230 nM). In vitro experiments show that 44e could inhibit the proliferation and induce apoptosis and autophagy-associated cell death of MDA-MB-231 and MDA-MB-468 cells. In two in vivo xenograft mouse models, 44e displays potent anticancer activity without obvious toxicities. Taken together, we successfully synthesized the first highly effective BRD4–CK2 dual inhibitor, which is expected to be an attractive therapeutic strategy for triple-negative breast cancer (TNBC).
Application of bioorthogonal hetero-Diels-Alder cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid and vinyl thioether for imaging inside living cells
Bazan, Bart?omiej,Pa?asz, Aleksandra,Skalniak, ?ukasz,Cie?, Dariusz,Buda, Szymon,J?drzejowska, Katarzyna,G?omb, Sonia,Kamzol, Daniel,Czarnota, Kinga,Latos, Krystian,Kozie?, Krzysztof,Musielak, Bogdan
supporting information, p. 6045 - 6058 (2021/07/25)
New bioorthogonal cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid as 1-oxa-1,3-butadienes and vinyl thioether as a dienophile has been applied to imaging inside living cells. The reaction is high yielding, selective, and fast in aqueous media. The proposed 1-oxa-1,3-butadiene derivative conjugated to a FITC fluorochrome selectively and rapidly labels the cancer cells pretreated with the dienophile-taxol. The second order rate constants k2 for various proposed bioorthogonal cycloadditions were estimated to be in the range from 0.9 × 10-2 M-1 s-1 to 1.4 M-1 s-1, which is much better than in the case of the first generation TQ-ligation (o-quinolinone quinone methide and vinyl thioether ligation, k2 = 1.5 × 10-3 M-1 s-1) and comparable or better to that for the second generation TQ-ligation (k2 = 2.8 × 10-2 M-1 s-1). The reaction rate constants k2 of proposed ligation reactions are in the range of the rate constants k2 for tetrazines and norbornenes or tetrazines and cyclopropenes. These findings indicate that this chemistry is suitable for in vitro imaging experiments.
Rational Design, Synthesis, and In Vitro Neuroprotective Evaluation of Novel Glitazones for PGC-1α Activation via PPAR-γ: a New Therapeutic Strategy for Neurodegenerative Disorders
Bharathi, Jeyabalan Jeyaram,Dhivya, S.,Divakar, Selvaraj,Durai, Priya,Justin, Antony,Kabadi, Pradeep,Mandal, Subhankar,Prabitha, P.,Prashantha Kumar, B. R.,Sandhya, C. H.,Sekhar, Satheesh John,Wadhwani, Ashish D.,Yuvaraj, S.
, (2019/12/15)
In the present study, two structurally diverse novel glitazones were designed and synthesized for activation of central PGC-1α signaling through stimulation of PPAR-γ receptor. The functional interaction between PGC-1α and PPAR-γ is a key interaction in the normal physiology of neuroprotective mechanism. Therefore, activation of PPAR-γ–dependent PGC-1α co-activator signaling could be an effective strategy to exhibit neuroprotection in several neurodegenerative disorders like Alzheimer’s disease, Parkinson’s disease, and cerebral ischemia. As part of rational design, analogs were designed manually based on principles of bioisosterism, followed by virtually screened using docking to predict the mode of interaction of compound towards the binding site and molecular dynamic simulation to observe the structural changes that occur during compound interaction with active site. The designed two glitazones (G1, G2) were synthesized and structurally analyzed. As part of evaluation, synthesized glitazones were subjected for preliminary neuroprotective evaluation in Lipopolysaccharide (LPS) intoxicated SH-SY5Y neuroblastoma cells. The results indicate that pre-treatment with synthesized glitazones have increased the percentage cell viability, protected the cell morphology, and decreased the release of pro-inflammatory cytokines (IL-1β, TNF-α), lipid peroxide (LPO), and nitric oxide (NO) level in LPS intoxicated SH-SY5Y cells. Interestingly, among the two glitazones, G2 has shown significant neuroprotection in comparison to G1 and neuroprotective effect exerted by G2 was similar and comparable with the standard pioglitazone. Altogether, neuroprotection exhibited by this non-thiazolidione–based glitazones during neuroinflammatory conditions may be attributed to the activation of central PGC-1α signaling via PPAR-γ receptor.
Chalcone aryloxyacetamide compound as well as preparation method and application thereof
-
Paragraph 0031-0032; 0038-0042, (2018/03/26)
The invention relates to the field of pharmaceutical chemistry, in particular to a chalcone aryloxyacetamide compound (I) or (II) and a preparation method thereof. As proved by a pharmacodynamic test,the compound has the effects of reducing blood glucose, reducing triglyceride and reducing cholesterol, and can be used for treating abnormal glucolipid metabolism and obesity. A general formula of the compound is shown in the description.
Design, synthesis chalcone derivatives as AdipoR agonist for type 2 diabetes
Zhu, Panhu,Huang, Weijun,Li, Jiaming,Ma, Xiaodong,Hu, Mengqi,Wang, Yujun,Xu, Qinlong,Wang, Xianna
, p. 1525 - 1536 (2018/06/04)
Two structurally novel series of chalcone derivatives were designed and synthesized as potential agents against type 2 diabetes. As a result of the antidiabetic biological evaluation in streptozotocin (STZ)-induced type 2 diabetes animal model, 13e, 13g, and 19f showed more significant reduction in serum Glu, TG, TC levels by contrast to the positive control AdipoRon. In addition to upregulating the expression of AdipoR1 and AdipoR2, 13e and 19f treatment also increased expression of AMPK and PPAR-α. Taken together, these results suggested that 13e and 19f might be a promising compound for type 2 diabetes treatment.
Carbon nitride assisted chemoselective C-H bond photo-oxidation of alkylphenolethoxylates in water medium
Ilkaeva,Krivtsov,Bartashevich,Khainakov,García,Díaz,Ordó?ez
supporting information, p. 4299 - 4304 (2017/09/29)
The unprecedented ability of g-C3N4 to chemoselectively photo-oxidise the methyl group of 2-(4-methylphenoxy)ethanol instead of the easily oxidised oxyethanol fragment has been demonstrated. When g-C3N4 is treat
Synthetic method of p-hydroxymethylphenoxyacetic acid serving as linker
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Paragraph 0005; 0013, (2017/03/08)
The invention relates to a synthetic method of p-hydroxymethylphenoxyacetic acid serving as a linker and aims at solving the technical problems that a traditional method is higher in cost, is unfavorable for body health and the like. The technical scheme adopted by the invention is that the synthetic method of the p-hydroxymethylphenoxyacetic acid serving as the linker comprises the following steps of condensing p-hydroxy benzaldehyde and chloroacetic acid under the alkaline condition to obtain p-formylphenoxyacetic acid; reducing the p-formylphenoxyacetic acid by using a reducing agent to obtain the p-hydroxymethylphenoxyacetic acid. The synthetic method disclosed by the invention is low in synthetic cost and is suitable for scale production.
