- Synthesis of chiral γ-lactones via a RuPHOX-Ru catalyzed asymmetric hydrogenation of aroylacrylic acids
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An asymmetric hydrogenation of aroylacrylic acids catalyzed by RuPHOX-Ru catalyst has been developed, affording the corresponding chiral γ-lactones in high yields and with up to 93% ee. The methodology has the advantage of utilizing easily accessible substrates and has therefore expand the scope of the resulting chiral γ-lactones. Furthermore, high catalytic efficiency was achieved in that the reduction of both the C[dbnd]C and C[dbnd]O double bonds was achieved in one step. The current work provides an alternative and convenient pathway for the synthesis of a wide range of chiral γ-lactones.
- Lu, Yufei,Li, Jing,Zhu, Yue,Shen, Jiefeng,Liu, Delong,Zhang, Wanbin
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supporting information
p. 3643 - 3649
(2019/05/29)
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- Photoinduced, Copper-Promoted Regio- and Stereoselective Decarboxylative Alkylation of α,β-Unsaturated Acids with Alkyl Iodides
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The first example of UV light-induced, copper-catalyzed regio- and stereoselective decarboxylative coupling of α,β-unsaturated acids with alkyl iodides was reported. Under standard conditions, the 1°, 2°, and 3° alkyl iodides proceeded smoothly with the E-selective alkenes obtained in uniformly good yields and high stereoselectivities.
- Wang, Chao,Lei, Yingjie,Guo, Mengzhun,Shang, Qinyu,Liu, Hong,Xu, Zhaoqing,Wang, Rui
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supporting information
p. 6412 - 6415
(2017/12/08)
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- 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 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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- Synthesis and evaluation of anticancer activity of some novel 6-aryl-2-(p-sulfamylphenyl)-pyridazin-3(2H)-ones
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A series of novel pyridazinone derivatives bearing benzenesulfonamide moiety (2a-h) has been synthesized by the condensation of appropriate aroylacrylic acid and 4-hydrazinobenzenesulfonamide hydrochloride in ethanol. Five derivatives (2a, 2b, 2d, 2g and 2h) were evaluated for their anticancer activity toward human cancer cell lines by the National Cancer Institute. The 2h showed remarkable activity against SR (leukemia) and NCI-H522 (non-small cell lung) with a GI50 value of less than 0.1 μM. It also displayed good activity against leukemia (CCRF-CEM, HL-60 (TB), K-562, MOLT-4, RPMI-8226), non-small cell lung cancer (NCI-H460), colon (HCT-116, HCT-15, HT29, KMI2, SW-620), CNS (SF-295), melanoma (MALME-3M, M14, MDA-MB-435 SK-MEL-5), ovarian (OVCAR-3, NCI/ADR-RES) and breast (MCF7) cancer cell lines with a GI 50 less than 1.0 μM. The acute toxicity study of 2h indicated that it is well tolerated intra-peritoneally (400 mg/kg) by athymic nude mice. The 2h may possibly be used as lead compound for developing new anticancer agents.
- Rathish,Javed, Kalim,Ahmad, Shamim,Bano, Sameena,Alam,Akhter, Mymoona,Pillai,Ovais, Syed,Samim, Mohammed
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scheme or table
p. 304 - 309
(2012/04/10)
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- The first example of a crystallization-induced asymmetric transformation (CIAT) in the Mannich reaction
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The novel synthesis of highly enantioenriched N-substituted α-amino-γ-alkyl(aryl)-γ-oxobutanoic acids is described. The process involves the combination of a crystallization-induced asymmetric transformation (CIAT) and the Mannich reaction. The role of retro-Mannich and retro-Michael reactions in the mechanism of the highly stereoselective transformation is also discussed.
- Jakubec, Pavol,Petras, Pavel,Duris, Andrej,Berkes, Dusan
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scheme or table
p. 69 - 74
(2010/04/24)
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- 4-Aryl-4-oxo-N-phenyl-2-aminylbutyramides as acetyl- and butyrylcholinesterase inhibitors. Preparation, anticholinesterase activity, docking study, and 3D structure-activity relationship based on molecular interaction fields
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Synthesis and anticholinesterase activity of 4-aryl-4-oxo-N-phenyl-2-aminylbutyramides, novel class of reversible, moderately potent cholinesterase inhibitors, are reported. Simple substituent variation on aroyl moiety changes anti-AChE activity for two orders of magnitude; also substitution and type of hetero(ali)cycle in position 2 of butanoic moiety govern AChE/BChE selectivity. The most potent compounds showed mixed-type inhibition, indicating their binding to free enzyme and enzyme-substrate complex. Alignment-independent 3D QSAR study on reported compounds, and compounds having similar potencies obtained from the literature, confirmed that alkyl substitution on aroyl moiety of molecules is requisite for inhibition activity. The presence of hydrophobic moiety at close distance from hydrogen bond acceptor has favorable influence on inhibition potency. Docking studies show that compounds probably bind in the middle of the AChE active site gorge, but are buried deeper inside BChE active site gorge, as a consequence of larger BChE gorge void.
- Vitorovi?-Todorovi?, Maja D.,Jurani?, Ivan O.,Mandi?, Ljuba M.,Drakuli?, Branko J.
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scheme or table
p. 1181 - 1193
(2010/04/06)
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- Synthesis and analgesic and antiinflammatory activity of 6-phenyl/(4-methylphenyl)-3(2H)-pyridazinon-2-propionamide derivatives
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For reducing gastrointestinal toxicity associated with non-steroidal anti-inflammatory drugs (NSAIDs) a variety of 6-phenyl/(4-methylphenyl)-3(2H)- pyridazinon-2-propionamide were synthesized. The structures of these new pyridazinone derivatives were confirmed by their IR, 1 H-NMR spectra and elementary analysis. All the new compounds were tested in vivo for their analgesic and anti-inflammatory activities. The analgesic activity of the test compounds was determined by phenylbenzoquinone-induced writhing assay and the anti-inflammatory activity was evaluated by the carrageenan-induced rat paw edema model. 6-Phenyl-3(2H)-pyridazinon-2-yl-[4-(4-fluorophenyl) piperazinyl] propanamide IV a-3 was the most active one among the synthesized compounds. Also this compound exhibited most potent anti-inflammatory activity. Acetylsalicylic acid and indometacin were used as reference drugs. Adverse effects of the compounds were examined on gastric mucosa. None of the compounds showed gastric ulcerogenic effect compared with the reference NSAIDs. ECV Editio Cantor Verlag.
- Goekce, Mehtap,Colak, Meral Sirin,Kuepeli, Esra,Sahin, Mustafa Fethi
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experimental part
p. 357 - 363
(2010/03/23)
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- Syntheses of 1,5-Benzothiazepines: Part II - Synthesis of 4-Aryl-2-carboxy-2,3-dihydro-1,5-benzothiazepines
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β-Aroylacrylic acids (II) react with 2-aminothiophenols (I) in ethanol containing gl.acetic acid to give 4-aryl-2-carboxy-2,3-dihydro-1,5-benzothiazepines (VII).Their structures have been established by elemental analyses and spectral data (IR, PMR, 13C NMR and mass).
- Pant, Umesh C.,Gaur, B. S.,Chugh, Manju
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p. 947 - 950
(2007/10/02)
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- SYNTHESIS AND SOME TRANSFORMATIONS OF VINYL β-ACETYL- AND β-BENZOYLACRYLATES
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Vinyl β-acetyl- and β-benzoylacrylates were obtained by transvinylation with vinyl acetate in the presence of the catalyst Hg(OCOCH3)2.BF3.O(C2H5)2.It was shown that the reactions with bromine, mercuric acetates, and butyl hydrosulfide at the vinyloxy group are regioselective.
- Komarova, L. I.,Zhuravlev, S. V.,Sal'nikova, L. V.
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p. 1422 - 1425
(2007/10/02)
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