- Microwave-associate synthesis of Co3O4 nanoparticles as an effcient nanocatalyst for the synthesis of arylidene barbituric and Meldrum's acid derivatives in green media
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In this study, Co3O4 nanocatalysts were constructed in environmentally appropriate conditions using controlled, effective, and facile microwave method. The final nanostructures were characterized by SEM, XRD, and TEM analyses. The products had a small size distribution, homogeneous morphology, and crystallographic structures associated with the formation of Co3O4 nanostructures. Moreover, EDS mapping analysis confirmed the existence of Co and O elements in the final structure, and the magnetic properties of the samples were investigated by VSM. The application of this nanostructure in a catalytic process was further examined, and the results suggested that it could be used as a novel candidate for the synthesis of arylidene barbituric and Meldrum,s acid through Knoevenagel condensation of aldehydes by barbituric and Meldrum,s acid in aqueous media. The high yield of these nanocatalysts would be justified by the nature of the nanostructure as well as the experimental procedure developed in this study, which affected the physicochemical features of the products.
- Yahyazadehfar, Mahdieh,Sheikhhosseini, Enayatollah,Ahmadi, Sayed Ali,Ghazanfari, Dadkhoda
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- Structurally simple D–A-type organic sensitizers for dye-sensitized solar cells: effect of anchoring moieties on the cell performance
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Abstract: In this work, we report synthesis and device fabrication studies of four metal-free D–A-type dyes (A1–A4) based on structurally simple N,N-dimethyl-4-vinyl aniline carrying four different acceptor/anchoring groups, as sensitizers for sensitizing photoanode (TiO2). In the sensitizers, N,N-dimethylaniline ring acts as an electron donor, while barbituric acid, N,N-dimethyl barbituric acid, thiobarbituric acid and N,N-diethyl thiobarbituric acid function as electron acceptor/anchoring units. They were synthesized in good yield via Knoevenagel protocol in neutral condition without any catalyst. Further, they were subjected to structural, electrochemical and optical characterization in order to evaluate their structure, band gap and absorption/emission behavior. The studies reveal that all the four dyes have thermodynamic feasibility of electron injection as well as electron recombination; their optical band gaps were found to be in the range of 2.35–2.56?eV. High-quality crystals of A2 and A4 were grown by slow evaporation technique using its solution with 1:1 pet ether (60–80?°C)/ethyl acetate solvent mixture at room temperature. Their SC-XRD studies disclose that the crystals are in the triclinic system with space group P-1. Further, DFT studies were performed using Turbomole V7.1 software package to evaluate their optimized geometry and HOMO and LUMO levels. Finally, DSSC device fabricated with the dye A1 showed relatively good efficiency when compared to other dyes mainly due to the effective binding of barbituric acid on the surface of TiO2 through NH or OH functional group. Graphical Abstract: [Figure not available: see fulltext.].
- Naik, Praveen,Su, Rui,Babu, Dickson D.,El-Shafei, Ahmed,Adhikari, Airody Vasudeva
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p. 2457 - 2466
(2017/10/30)
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- The synthesis and evaluation of near-infrared probes with barbituric acid acceptors for in vivo detection of amyloid plaques
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A new array of near-infrared probes containing barbituric acid acceptors has been developed as Aβ imaging agents. These probes displayed long-emission wavelengths and large Stokes shifts, as well as high affinities for Aβ aggregates. In vivo and ex vivo studies demonstrated that BBTOM-3 could intensely label Aβ plaques in the brains of transgenic mice.
- Zhou, Kaixiang,Fu, Hualong,Feng, Liang,Cui, Mengchao,Dai, Jiapei,Liu, Boli
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supporting information
p. 11665 - 11668
(2015/07/15)
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- Synthesis and structure-activity relationship of thiobarbituric acid derivatives as potent inhibitors of urease
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A series of thiobarbituric acid derivatives 1-27 were synthesized and evaluated for their urease inhibitory potential. Exciting results were obtained from the screening of these compounds 1-27. Compounds 5, 7, 8, 11, 16, 17, 22, 23 and 24 showed excellent urease inhibition with IC50 values 18.1 ± 0.52, 16.0 ± 0.45, 16.0 ± 0.22, 14.3 ± 0.27, 6.7 ± 0.27, 10.6 ± 0.17, 19.2 ± 0.29, 18.2 ± 0.76 and 1.61 ± 0.18 μM, respectively, much better than the standard urease inhibitor thiourea (IC50 = 21 ± 0.11 μM). Compound 3, 4, 10, and 26 exhibited comparable activities to the standard with IC50 values 21.4 ± 1.04 and 21.5 ± 0.61μM, 22.8 ± 0.32, 25.2 ± 0.63, respectively. However the remaining compounds also showed prominent inhibitory potential The structure-activity relationship was established for these compounds. This study identified a novel class of urease inhibitors. The structures of all compounds were confirmed through spectroscopic techniques such as EI-MS and 1H NMR.
- Khan, Khalid Mohammed,Rahim, Fazal,Khan, Ajmal,Shabeer, Muhammad,Hussain, Shafqat,Rehman, Wajid,Taha, Muhammad,Khan, Momin,Perveen, Shahnaz,Choudhary, M. Iqbal
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p. 4119 - 4123
(2014/08/18)
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- Synthesis, theoretical investigation of 5-(4-dimethylaminobenzylidene) thiobarbituric acid
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In this study, synthesis of 5-benzylidene thiobarbituric acid derivative has been described. The route of preparation involved the uses of thiobarbituric acid as starting material and treated with 4-dimethylaminobenzaldehyde compound to give required derivative. This compound was identified by spectroscopic methods; H NMR, FTIR and CHNS analysis and also by measuring its melting point. A theoretical investigation is performed using hybrid Beck model (B3LYP), ESP showed regular distribution of charge density of whole molecule when one of the two proton is removed from ?-carbon, the ESP for HOMO electron density is heavily localized on α negative carbon, reflect the reactivity of thiobarbituric molecule and show it as highly effective nucleophile when act into nucleophilic substitution reactions.
- Mageed, Ahmed .H.,AL-Ameed, Karrar A.S.
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p. 2953 - 2955
(2013/05/21)
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- Facile syntheses of bioactive 5-arylidenethiobarbituric acids
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A simple and green chemistry route for the preparation of 5-arylidenethiobarbituric acids has been developed by Knoevenagel condensation of thiobarbituric acid with different aromatic and heteroaromatic aldehydes using catalytic amount of acetic acid by g
- Sharif, Ahsan,Ahmed, Ejaz,Munawar, Munawar Ali,Jabeen, Shamsa,Khan, Misbah-Ul-Ain,Begum, Robina,Farrukh, Aleeza,Ashraf, Muhammad,Arshad, Shafia,Afza, Nighat
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experimental part
p. 578 - 586
(2012/01/05)
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- Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice
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A large amount of evidence suggests that monocytes/macrophages infiltration is implicated in a variety of inflammatory diseases including acute liver injury. Monocyte chemoattractant protein 1 (MCP-1) plays a crucial role in the process of macrophages recruitment. We herein presented a small-molecule library and a feasible quick screening method of evaluating potency of inhibition of chemotaxis of RAW264.7 cells stimulated by MCP-1. Fifty-three small molecules were synthesized and screened, and four compounds (2g, 2h, 4f, and 6h) showed inhibitory effects with IC50 values range from 0.72 to 20.47 μM, with compound 4f being the most efficient. Further in vivo studies demonstrated that oral administration of 2g, 2h, 4f, or 6h decreases, most significantly for 4f, the serum levels of alanine aminotransaminase (ALT) and asparate aminotransaminase (AST) in ConA-induced acute livery injury BALB/c mice. Histopathological evaluation liver sections confirmed 4f as a potent, orally active compound for hepatoprotective effects against ConA-induced acute liver injury in BALB/c mice.
- Luo, Youfu,Ma, Liang,Zheng, Hao,Chen, Lijuan,Li, Rui,He, Chunmei,Yang, Shengyong,Ye, Xia,Chen, Zhizhi,Li, Zicheng,Gao, Yan,Han, Jing,He, Gu,Yang, Li,Wei, Yuquan
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experimental part
p. 273 - 281
(2010/05/02)
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- Nickel nanoparticles catalyzed knoevenagel condensation of aromatic aldehydes with barbituric acids and 2-thiobarbituric acids
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An efficient route for the Knoevenagel condensation of aromatic aldehydes with barbituric acids and 2-thiobarbituric acids in the presence of polyvinyl pyrrolidone (PVP) stabilized Ni nanoparticles in ethylene glycol has been reported. A range of biologically important arylidene barbiturates were obtained in high yields (82-97%) in a very short reaction time. Graphical Abstract: A novel and highly efficient PVP-stabilized Ni nanoparticles catalyzed synthesis of arylidene barbiturates and arylidene 2-thiobarbiturates has been described.
- Khurana, Jitender M.,Vij, Kanika
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experimental part
p. 104 - 110
(2010/11/05)
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- Synthesis of barbiturate-based methionine aminopeptidase-1 inhibitors
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The syntheses of a new class of barbiturate-based inhibitors for human and Escherichia Coli methionine aminopeptidase-1 (MetAP-1) are described. Some of the synthesized inhibitors show selective inhibition of the human enzyme with high potency.
- Haldar, Manas K.,Scott, Michael D.,Sule, Nitesh,Srivastava,Mallik, Sanku
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p. 2373 - 2376
(2008/09/20)
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- 1-n-butyl-3-methylimmidazolium tetrafluoroborate-promoted green synthesis of 5-arylidene barbituric acids and thiobarbituric acid derivatives
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The room temperature ionic liquid 1-n-butyl-3-methylimmidazolium tetra-fluoroborate ([bmim]BF4) was used to promote the synthesis of 5-arylidene barbituric acids and thiobarbituric acid derivatives under the solid-state conditions of grinding or microwave irradiation without organic solvent. The yields were 77.9-96.2%. It is shown that the proposed method is fast, efficient, and environmentally benign. Copyright Taylor & Francis, Inc.
- Wang, Chun,Ma, Jing-Jun,Zhou, Xin,Zang, Xiao-Huan,Wang, Zhi,Gao, Yong-Jun,Cui, Peng-Lei
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p. 2759 - 2764
(2007/10/03)
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- Organic reactions in ionic liquids: Ionic liquid promoted Knoevenagel condensation of aromatic aldehydes with (2-thio)barbituric acid
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The Knoevenagel condensation of aromatic aldehydes with (2-thio)barbituric acid proceeded efficiently in reusable ionic liquids, EAN, BmimBF4, and BmimPF6 at room temperature in the absence of any catalyst with high yields.
- Hu, Yi,Chen, Zhen-Chu,Le, Zhang-Gao,Zheng, Qin-Guo
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p. 4521 - 4529
(2007/10/03)
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- Green chemistry approaches to the synthesis of 5-arylidenethiobarbituric acids by a condensation reactions between aromatic aldehydes and thiobarbituric acid: Comparison of water, microwave irradiation, and grinding
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A general and practical green chemistry route to the synthesis of 5-arylidenethiobarbituric acids is described from aromatic aldehydes and thiobarbituric acid under three different sets of reaction conditions: water without catalyst conditions, microwave
- Lu, Jun,Li, Yingying,Bai, Yinjuan,Tian, Min
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p. 583 - 589
(2007/10/03)
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- Spectrophotometric determination and kinetic studies of condensation of aromatic aldehydes with 2-thiobarbituric acid
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The condensation reaction of 2-thiobarbituric acid with aromatic aldehydes in ethanol has been investigated spectrophotometrically at 30-50°C. The reaction was catalyzed by HCl solutions. The reaction follows overall second order kinetics, first order eac
- Medien,Zahran
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p. 1069 - 1080
(2007/10/03)
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- New Aspects in the Reaction of Azomethines with Cyclic CH-Acidic Compounds
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Treatment of substituted benzylidene anilines 1a - f with cyclic CH-acidic compounds 2a - m in ethanol at room temperature yields in addition/elimination reactions the corresponding arylidene derivatives 4 and the 2:1 adducts 5.The addition products 3, which are formed as intermediates, could not be isolated in any case.The donor/acceptor effect of the substituents on the benzylidene moiety influences to a significant extent the reactivity towards the azomethine carbon. Keywords.Azomethine; CH-Acidic compound; Addition/elimination reaction.
- Hennig, Lothar,Alva-Astudillo, Mario,Mann, Gerhard,Kappe, Thomas
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p. 571 - 580
(2007/10/02)
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- Kinetics and mechanism of reaction of barbituric acids with p-dimethylaminobenzaldehyde and N,N-dimethyl-p-nitrosoaniline
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The condensation reactions of barbituric acid (I) and thiobarbituric acid (II) with p-dimethylaminobenzaldehyde (III) and N,N-dimethyl-p-nitrosoaniline (IV) in methanolic medium have been investigated spectrophotometrically at 10-55 deg C.These reactions follow overall second order kinetics, first order each in reactants.The rate-determining step involves dehydration of the aldol intermediate (XI).From the dependence of the rate constants on temperature activation parameters have been calculated.The solvent effect on the reaction rate has been investigated and therate decreases with decrease in dielectric constant.
- Girgis, Maher M,El-Shahawy, A S
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