- Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids
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Abstract: Here it is described the synthesis, antioxidant and antimicrobial activity determination of novel rel-(5 R, 6 S, 7 R)-6-benzoyl-7-phenyl-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-5-carboxylic acids. The target compounds were obtained in good yields from 5-arylidene-4-thioxo-2-thiazolidinones and β -aroylacrylic acids via regio- and diastereoselective hetero-Diels–Alder reaction. The stereochemistry of the cycloaddition was confirmed by NMR spectra. The antioxidant and antimicrobial activity screening identified 7 compounds (3c, 3e, 3f, 3g, 3k, 3l, 3p) with a high level of free radical scavenging (43–77% DPPH assay), and compounds with significant influence on Staphylococcus aureus, Bacillus subtilis and Candida albicans (MIC 3.13–6.25 μ g/mL), but slight effect on Escherichia coli.
- Lozynskyi, Andrii,Zasidko, Viktoria,Atamanyuk, Dmytro,Kaminskyy, Danylo,Derkach, Halyna,Karpenko, Olexandr,Ogurtsov, Volodymyr,Kutsyk, Roman,Lesyk, Roman
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p. 427 - 436
(2017/05/29)
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- Synthesis and applications of pyridazinones for base oil improvement
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THREE pyridazinone derivatives of the type 4,5-dihydropyridazin- 3(2H)-ones, N-(4-(6-oxo-5- ((5-phenyl-1,3,4-thiadiazol-2-yl)amino) - 1,4,5,6 - tetrahydropyridazin - 3-yl) phenyl) acetamide (4a), 6-(4-chlorophenyl)-4-((5-phenyl-1,3,4-thiadiazol-2-yl)amino)-4,5-di-hydropyridazin-3 (2H)-one (4b) and 6-(4-bromophenyl) -4- ((5-phenyl-1,3,4-thiadiazol-2-yl) amino)-4,5-dihydropyridazin-3(2H)-one (4c) were synthesized. They were characterized by the conventional tools of analysis, Elemental analysis, IR and 1H-NMR spectroscopy. The tools of analysis confirmed the structure of the three prepared compounds. These heterocyclic compounds are chemically stable and possess multi actions for base oil improvement. They are tested as antioxidants for local base oil through the change in total acid number (TAN). They gave good results as antioxidants for base oil. Also these three synthesized compounds are tested as corrosion inhibitors for carbon steel in acid medium. The efficiency order for these tested compounds is ranked as follows: 4a > 4b > 4c. Energy of the highest occupied molecular orbital (EHOMO) and lowest unoccupied molecular orbital (ELUMO) for the three prepared compounds were calculated via the Ab initio method. Studying of the quantum chemical calculations of the synthesized compounds showed good matching with the experimental results.
- Rizk,Attia,Osman, Doaa I.,Nessim
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p. 129 - 146
(2017/06/13)
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- Pyridazinone substituted benzenesulfonamides as potent carbonic anhydrase inhibitors
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A series of sulfonamide derivatives (2a-l) incorporating substituted pyridazinone moieties were investigated for the inhibition of two human cytosolic carbonic anhydrase isoforms, hCA I and hCA II. All these compounds, together with the clinically used su
- Yaseen, Raed,Ekinci, Deniz,Senturk, Murat,Hameed, Alhamzah Dh.,Ovais, Syed,Rathore, Pooja,Samim, Mohammed,Javed, Kalim,Supuran, Claudiu T.
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p. 1337 - 1341
(2016/02/23)
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- Synthesis and biological evaluations of 1,2-diaryl pyrroles as analogues of combretastatin A-4
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A series of novel 1,2-diaryl pyrroles as analogues of combretastatin A-4 (CA-4, 1a) were synthesized and evaluated for their antitumour potential against three cancer cell lines. Most compounds exhibited growth inhibition against all of the cancer cell lines. Compound 7q not only exhibited prominent antitumour efficacy with IC50 values of 0.390 μm in SGC-7901, 0.070 μm in HT-1080 and 0.045 μm in KB cell lines but also showed low activity with IC50 values of 30.08 μm in normal L929 cell line. Moreover, compound 7q inhibited tubulin polymerization into microtubules and caused microtubule destabilization. A molecular docking study of 7q was performed to determine its binding mode at the colchicine site in the tubulin dimer. 1,2-Diaryl pyrroles as combretastatin A-4 analogues were synthesized and evaluated for anti-proliferative activities. Compound 7q exhibited antitubulin activity.
- Sun, Jun,Chen, Lei,Liu, Chunjiang,Wang, Zhan,Zuo, Daiying,Pan, Jiatong,Qi, Huan,Bao, Kai,Wu, Yingliang,Zhang, Weige
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p. 1541 - 1547
(2016/02/05)
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- Synthesis of 1,5-benzodiazepine derivatives using p-toluenesulfonic acid as catalyst
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A series of substituted ethyl 4-oxo-4-phenylbut-2-enoates were prepared and reacted with substituted o-phenylenediamine, undergone Michael addition reactions and cyclodehydration to provide novel 4-phenyl-2,3-dihydro-1,5-benzodiazepine-2-carboxylate derivatives with excellent yields. The synthetic protocol fulfilled many green-chemical requirements by using simple catalyst p-toluenesulfonic acid as activator and ethanol as solvent at room temperature.
- Wang, Shasha,Hu, Lijuan,Cheng, Suyan,Wang, Lanzhi
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p. 419 - 424
(2015/01/30)
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- Structure-activity relationship, cytotoxicity and mode of action of 2-ester-substituted 1,5-benzothiazepines as potent antifungal agents
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Our studies examined the structural features responsible for the antifungal activity of 2-ethoxycarbonyl-1,5-benzothiazepine (7a). Three series of 1,5-benzothiazepine derivatives were synthesized and screened for their antifungal activity. The results suggested that the ethoxycarbonyl group at the 2 position and the imine moiety on the seven-membered ring are essential for activity. The most potent of the synthesized analogues (7a, 7b) were further studied by evaluating their cytotoxicity and mode of action (for 7a). The results showed that compounds 7a and 7b were relatively safe for BV2 cells, but compound 7a interfered with Cryptococcus neoformans cell wall integrity by increasing the chitinase activity. Therefore, compound 7a was considered safe as an antifungal agent for animal cells. Three series of 1,5-benzothiazepine derivatives were synthesized and their antifungal activities were evaluated to determine the structure-activity relationships with respect to the antifungal activity of 2-ester-substituted 1,5-benzothiazepines. The effective antifungal compounds 7a and 7b were further studied for their antifungal activity, cytotoxicity and mechanism of action (for compound 7a). The results provided important information about this class of benzothiazepines. Copyright
- Kang, Wang,Du, Xingqiong,Wang, Lanzhi,Hu, Lijuan,Dong, Yuhuan,Bian, Yanqing,Li, Yuan
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p. 1305 - 1314
(2013/11/06)
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- Utility of β-aroyl acrylic acid in heterocyclic synthesis
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β-(4-bromobenzoyl) acrylic acid has been reacted with nitrogen nucleophiles namely ethanolamine and o-aminophenol and yielded the corresponding adduct la,b. On the other hand, ss-(3,4dichlorobenzoyl) acrylic acid has been reacted with carbon nucleophiles
- Rizk,El-Hashash,Mostafa
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experimental part
p. 611 - 621
(2010/09/05)
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