- Base-Promoted Annulative Difluoromethylenation of Enaminones with BrCF2CO2Et toward 2,2-Difluorinated 2,3-Dihydrofurans
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A practical method for the synthesis of 2,2-difluorinated 2,3-dihydrofurans has been established via the [4 + 1] annulation of enaminones and BrCF2CO2Et with Na2CO3 promotion. This new protocol does not employ any transition metal reagent and enables the annulative difluoromethylation by the partial cleavage of the C═C double bond. In addition, the further treatment with hydrochloric acid in one pot leads to β-keto enoic acids (4-oxo-2-butenoic acids) via a formal enaminone C-N carboxylation.
- Ying, Jinbiao,Liu, Ting,Liu, Yunyun,Wan, Jie-Ping
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p. 2404 - 2408
(2022/04/07)
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- Isocyanide-based MCRs: Diastereoselective cascade synthesis of perfluoroalkylated pyrano[3,4-c]pyrrole derivatives
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The highly diastereoselective synthesis of perfluoroalkyl-containing pyrano[3,4-c]pyrroles has been accomplished via a cascade process involving Michael addition, Passerini-type reaction, Mumm rearrangement and an oxo-Diels–Alder reaction. This domino tra
- Yang, Shanxue,Yao, Lan,Fan, Zhenhua,Han, Jing,Chen, Jie,He, Weimin,Deng, Hongmei,Shao, Min,Zhang, Hui,Cao, Weiguo
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supporting information
(2021/02/03)
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- Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water
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A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is
- Li, Tiejun,Peng, Henian,Tang, Wenjun,Tian, Duanshuai,Xu, Guangqing,Yang, He
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p. 4327 - 4337
(2021/05/31)
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- 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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- A sertraline hydrochloride impurity preparation method (by machine translation)
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The invention discloses a sertraline hydrochloride preparation method of impurities, in particular comprising a formula 6 by the Leuckart reaction to obtain a compound of the formula 7 compound, with the insulated hydrochloride salt obtained in the reaction formula 8 cis-isomer of the compound, wherein the formula 6 compound in the location of the chloropropyl substituted cyclohexanone substituted meta or para position. Preparation method of this invention is simple, high purity, obtained impurity can be used for qualitative and quantitative analysis, so as to improve the safety of medicine sertraline hydrochloride. (by machine translation)
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Paragraph 0039; 0040
(2019/06/08)
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- Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents
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A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against MTB with MIC ranging from 0.125 to 4 μg/mL. Especially, compound IIIa16 was found to have the best activity with MIC of 0.125 μg/mL against MTB and with MIC in the range of 0.05–0.48 μg/mL against drug-resistant clinical MTB isolates.
- Ren, Jinfeng,Xu, Jian,Zhang, Guoning,Xu, Changliang,Zhao, LiLi,You, XueFu,Wang, Yucheng,Lu, Yu,Yu, Liyan,Wang, Juxian
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supporting information
p. 539 - 543
(2019/01/09)
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- Design, synthesis and biological evaluation of benzoylacrylic acid shikonin ester derivatives as irreversible dual inhibitors of tubulin and EGFR
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In this study, a series of shikonin derivatives combined with benzoylacrylic had been designed and synthesized, which showed an inhibitory effect on both tubulin and the epidermal growth factor receptor (EGFR). In vitro EGFR and cell growth inhibition assay demonstrated that compound PMMB-317 exhibited the most potent anti-EGFR (IC50 = 22.7 nM) and anti-proliferation activity (IC50 = 4.37 μM) against A549 cell line, which was comparable to that of Afatinib (EGFR, IC50 = 15.4 nM; A549, IC50 = 6.32 μM). Our results on mechanism research suggested that, PMMB-317 could induce the apoptosis of A549 cells in a dose- and time-dependent manner, along with decrease in mitochondrial membrane potential (MMP), production of ROS and alterations in apoptosis-related protein levels. Also, PMMB-317 could arrest cell cycle at G2/M phase to induce cell apoptosis, and inhibit the EGFR activity through blocking the signal transduction downstream of the mitogen-activated protein MAPK pathway and the anti-apoptotic kinase AKT pathway; typically, such results were comparable to those of afatinib. In addition, PMMB-317 could suppress A549 cell migration through the Wnt/β-catenin signaling pathway in a dose-dependent manner. Additionally, molecular docking simulation revealed that, PMMB-317 could simultaneously combine with EGFR protein (5HG8) and tubulin (1SA0) through various forces. Moreover, 3D-QSAR study was also carried out, which could optimize our compound through the structure-activity relationship analysis. Furthermore, the in vitro and in vivo results had collectively confirmed that PMMB-317 might serve as a promising lead compound to further develop the potential therapeutic anticancer agents.
- Bao, Jia-Xin,Fu, Jiang-Yan,Han, Hong-Wei,Lin, Hong-Yan,Lu, Gui-Hua,Lu, Yun-Ting,Qi, Jin-Liang,Sun, Wen-Xue,Wang, Ming-Yue,Wang, Xiao-Ming,Wang, Yin-Song,Wen, Zhong-Ling,Yang, Min-Kai,Yang, Yong-Hua
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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 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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- 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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- (E)-4-Aryl-4-oxo-2-butenoic acid amides, chalcone-aroylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization
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Antiproliferative activity of twenty-nine (E)-4-aryl-4-oxo-2-butenoic acid amides against three human tumor cell lines (HeLa, FemX, and K562) is reported. Compounds showed antiproliferative activity in one-digit micromolar to submicromolar concentrations.
- Vitorovic-Todorovic, Maja D.,Eric-Nikolic, Aleksandra,Kolundzija, Branka,Hamel, Ernest,Ristic, Slavica,Juranic, Ivan O.,Drakulic, Branko J.
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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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- Substituted pyridines as inhibitors of dipeptidyl peptidase IV and their application for the treatment of diabetes and related diseases
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The present invention relates to novel 2-aryl and 4-aryl substituted pyridines, which are highly selective and potent inhibitors of the dipeptidyl peptidase IV enzyme, and which are useful in the treatment and prevention of multiple diseases and disorders
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Page/Page column 18
(2011/04/25)
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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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- Catalytic conjugate addition of indoles to 4-aryl-4-oxobut-2-enoates by FeCl3
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The conjugate addition of indoles to 4-aryl-4-oxobut-2-enoates was achieved with FeCl3 as a catalyst under mild conditions. The reaction was highly regioselective and afforded a variety of new 3-substituted indoles in good to excellent yields. Copyright
- Wang, Xiaoxia,Zhang, Yaohong,Xiao, Xiaohui,Li, Xinsheng
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supporting information; experimental part
p. 1284 - 1285
(2009/12/03)
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- Utility of β-(4-chlorobenzoyl)acrylic acid in heterocyclic synthesis
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β-(4-Chlorobenzoyl)acrylic acid (1) proved to be a convenient precursor for the synthesis of a variety of heterocyclic systems through the reaction with compounds containing active methylene groups under Michael reaction conditions. Also, the reactivity o
- Eissa
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p. 1205 - 1214
(2007/10/03)
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- 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids selectively suppressed proliferation of neoplastic human HeLa cells. A SAR/QSAR study
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A series of twenty alkyl-, halo-, and methoxy-aryl-substituted 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids were synthesized. The new compounds, called CSAB, suppressed proliferation of human cervix carcinoma, HeLa cells, in vitro in a concentration range of 0.644 to 29.48 μM/L. Two compounds exhibit antiproliferative activity in sub-micromolar concentrations (16, 19). Five compounds act in low micromolar concentrations ( 10). A strong structure-activity relationship, using estimated log P values and BCUT descriptors, was observed.
- Drakuli?, Branko J.,Jurani?, Zorica D.,Stanojkovi?, Tatjana P.,Jurani?, Ivan O.
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p. 5600 - 5603
(2007/10/03)
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- Gastric anti-secretory, anti-ulcer and cytoprotective properties of substituted (E)-4-phenyl- and heteroaryl-4-oxo-2-butenoic acids
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A class of anti-secretory, anti-ulcer and cytoprotective agents, the substituted (E)-4-phenyl and heteroaryl-4-oxo-2-butenoic acids, is described.This chemical structure is not related to those of any known anti-cholinergic drugs, histamine H2-receptor antagonists or prostaglandins.Five compounds, 4-(2-methoxyphenyl)- 15, 4-(4-methoxyphenyl)- 22, 4-(3,4-dimethoxyphenyl)- 32, 4-(3,4,5-trimethoxyphenyl)- 40, and 4-(2-furanyl)-4-oxo-2-butenoic acid 44, have cytoprotective activity at a very low dose (0.6 mg/kg, p.o.) and anti-secretory and anti-ulcer activities at higher doses.One of these compounds, RU 38086 40, has been selected for clinical evaluation.Keywords - anti-ulcer agents / cytoprotective agents / (E)-4-phenyl- and heteroaryl-4-oxo-2-butenoic acids.
- Bianchi, Mario,Butti, Alina,Christidis, Yani,Perronnet, Jacques,Barzaghi, Fernando,et al.
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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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- Gastro-protecting activity
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Diseases and ailments accompanied by gastric and gastroduodenal lesions treated by administering a compound of the formula (I) STR1 in which R represents hydrogen or alkyl containing 1 to 5 carbon atoms and R1 and R2, identical or different, both represent alkoxy containing 1 to 3 carbon atoms, or both represent halogen, or R1 represents hydrogen and R2 represents halogen, nitro or trifluoromethyl, or R1 and R2 form a methylenedioxy group at adjacent carbon atoms, as well as pharmaceutically acceptable salts thereof, particularly alkali metal, alkaline earth metal, or amine salts of said acid.
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- Mercaptoacyldihydropyrazole carboxylic acid derivatives
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Hypertension can be treated using compounds having the formula or a basic salt thereof, wherein R1 is hydrogen, alkyl, aryl, arylalkyl or STR1 wherein R5 is alkyl or aryl; R2 is hydrogen or alkyl; R3 is aryl; R4 is hydrogen, alkyl or arylalkyl and n is 0, 1 or 2.
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- 3-(Benzoyl)oxiranecarboxamides
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Novel trans-isomers of 3-(benzoyl)oxiranecarboxamides, useful as lipogenesis inhibitors in warm-blooded animals.
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