- Assessing the potential of para-donor and para-acceptor substituted 5-benzylidenebarbituric acid derivatives as push–pull electronic systems: Experimental and quantum chemical study
-
Electronic interactions in donor-π-linker-acceptor systems with barbituric acid as an electron acceptor and possible electron donor were investigated to screen promising candidates with a push–pull character based on experimental and quantum chemical studies. The tautomeric properties of 5-benzylidenebarbituric acid derivatives were studied with NMR spectra, spectrophotometric determination of the pKa values, and quantum chemical calculations. Linear solvation energy relationships (LSER) and linear free energy relationships (LFER) were applied to the spectral data - UV frequencies and 13C NMR chemical shifts. The experimental studies of the nature of the ground and excited state of investigated compounds were successfully interpreted using a computational chemistry approach including ab initio MP2 geometry optimization and time-dependent DFT calculations of excited states. Quantification of the push–pull character of barbituric acid derivatives was performed by the 13CNMR chemical shift differences, Mayer π bond order analysis, hole-electron distribution analysis, and calculations of intramolecular charge transfer (ICT) indices. The results obtained show, that when coupled with a strong electron-donor, barbituric acid can act as the electron-acceptor in push–pull systems, and when coupled with a strong electron-acceptor, barbituric acid can act as the weak electron-donor.
- Stojiljkovi?, Ivana N.,Ran?i?, Milica P.,Marinkovi?, Aleksandar D.,Cvijeti?, Ilija N.,Mil?i?, Milo? K.
-
supporting information
(2021/02/26)
-
- Knoevenagel condensation in aqueous media promoted by 2,2′-bipyridinium dihydrogen phosphate as a green efficient catalyst
-
A 2,2′-Bipyridine-based ionic compound named 2,2′-bipyridinium dihydrogen phosphate was synthesized by addition of phosphoric acid to a solution of 2,2′-Bipyridine in dichloromethane. After the characterization using FT-IR, mass, 1H, 13C and 31P NMR techniques, it was used as a Bronsted dicationic acidic catalyst for the promotion of the synthesis of 2-arylidene malononitrile and 5-arylidene barbituric acid derivatives via Knoevenagel condensation reaction in water. Some of the advantages of this method are the utilization of an easy preparable, cost-effective and eco-friendly organic salt as a catalyst within high rates and yields of the reactions, simple and quick work-up and acceptable reusability of the catalyst.
- Darvishzad, Shila,Daneshvar, Nader,Shirini, Farhad,Tajik, Hassan
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p. 2973 - 2984
(2021/04/19)
-
- Microwave-associate synthesis of Co3O4 nanoparticles as an effcient nanocatalyst for the synthesis of arylidene barbituric and Meldrum's acid derivatives in green media
-
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
-
-
- Preparation and application of triphenyl(propyl-3-hydrogen sulfate)phosphonium bromide as new efficient ionic liquid catalyst for synthesis of 5-arylidene barbituric acids and pyrano[2,3-d]pyrimidine derivatives
-
We report synthesis of triphenyl(propyl-3-hydrogen sulfate)phosphonium bromide ([TPPHSP]Br) as a reusable green Br?nsted-acidic ionic liquid catalyst and its application for synthesis of 5-arylidene barbituric acids and pyrano[2,3-d]pyrimidine derivatives by condensation reaction between aromatic aldehydes and barbituric acid or aromatic aldehydes, malononitrile, and barbituric acid in EtOH–H2O in reflux condition with good to excellent yield. The [TPPHSP]Br IL catalyst was characterized by Fourier-transform infrared (FT-IR) spectroscopy, 1H and 13C nuclear magnetic resonance (NMR), and thermogravimetric (TG) analysis and showed good catalytic activity and reusability.
- Karami, Samira,Momeni, Ahmad Reza,Albadi, Jalal
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p. 3395 - 3408
(2019/04/25)
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- Verjuice as a green and bio-degradable solvent/catalyst for facile and eco-friendly synthesis of 5-arylmethylenepyrimidine-2,4,6-trione, pyrano[2,3-d]pyrimidinone and pyrimido[4,5-d]pyrimidinone derivatives
-
Verjuice (unripe grape juice), a natural mixture of organic acids, which is identified by pH-metric and TGA analysis, is efficiently used for the promotion of the synthesis of 5-arylmethylenepyrimidine-2,4,6-triones, via Knovenagel condensation reaction between barbituric or thiobarbituric acid and aldehydes. Verjuice is also employed for the effective synthesis of pyrano[2,3-d]pyrimidinone derivatives via a three-component reaction of barbituric acid or its thio analogue, aldehydes and malononitrile. In the same way, pyrimido[4,5-d]pyrimidinone derivatives are simply produced via the reaction of barbituric acid, aldehydes and urea or thiourea in the presence of verjuice. This green methodology rewards notable advantages including simple procedures, acceptable reaction times, easy work-up, high yields, circumventing the use of any expensive starting materials, volatile and hazardous organic solvents during the reaction and work-up process, and use of a natural, low-cost, reusable, and bio-degradable catalyst.
- Safari, Niloufar,Shirini, Farhad,Tajik, Hassan
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p. 887 - 897
(2019/03/27)
-
- Butane-1-sulfonic acid immobilized on magnetic Fe3O4@SiO2 nanoparticles: A novel and heterogeneous catalyst for the one-pot synthesis of barbituric acid and pyrano[2,3-d] pyrimidine derivatives in aqueous media
-
Butane-1-sulfonic acid immobilized on magnetic Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2-Sultone) was easily prepared via direct ring opening of 1,4-butanesultone with nanomagnetic Fe3O4@SiO2. The prepared reagent was characterized and used for the efficient promotion of the synthesis of barbituric acid and pyrano[2,3-d] pyrimidine derivatives. All reactions were performed under mild and completely heterogeneous reaction conditions affording products in good to high yields. The catalyst is easily isolated from the reaction mixture by magnetic decantation and can be reused at least eight times without significant loss in activity.
- Pourghasemi-Lati,Shirini,Alinia-Asli,Rezvani
-
-
- The introduction of two new imidazole-based bis-dicationic Br?nsted acidic ionic liquids and comparison of their catalytic activity in the synthesis of barbituric acid derivatives
-
In this article, the preparation of bis-imidazolium hydrogen sulfate and bis-imidazolium perchlorate as two new bis-dicationic Br?nsted acidic ionic liquids based on imidazole is reported. After characterization by FT-IR, mass and NMR spectroscopy and pH titration, the applicability of these reagents is studied in the promotion of the synthesis of 5-arylidene barbituric acids and pyrano[2,3-d] pyrimidinone derivatives. These methods possess some advantages such as ease of preparation of the catalyst, simple work-up procedure, short reaction times, excellent yields, and use of nonorganic solvents during all steps of the reactions and good reusability of the catalysts.
- Daneshvar, Nader,Nasiri, Mitra,Shirzad, Maryam,Safarpoor Nikoo Langarudi, Mohaddeseh,Shirini, Farhad,Tajik, Hassan
-
p. 9744 - 9756
(2018/06/18)
-
- 4-(4-Propylpiperazine-1-yl)butane-1-sulfonic acid-modified silica-coated magnetic nanoparticles: A novel and recyclable catalyst for the synthesis of 5-arylidinebarbituric acids and pyrano[2,3-d]pyrimidinedione derivatives in aqueous media
-
A mild, simple and efficient procedure for the preparation of barbituric acid and pyrano[2,3-d]pyrimidine derivatives in aqueous media is described using 4-(4-propylpiperazine-1-yl)butane-1-sulfonic acid-modified silica-coated magnetic nanoparticles as a novel and reusable catalyst. The catalyst was easily isolated from the reaction mixture by magnetic decantation using an external magnet and reused at least eight times without significant degradation in activity.
- Pourghasemi-Lati,Shirini,Alinia-Asli,Rezvani
-
-
- A facile single pot synthesis of highly functionalized tricyclic heterocycle compounds via sequential Knoevenagel-Michael addition and their α-glucosidase inhibition, antioxidants and antibacterial studies
-
A facile methodology was developed which involved multicomponent single pot reaction which yielded the synthesis of highly functionalized tricyclic-heterocycle compounds (1c-6c) and (1d-7d) in good yields (60-80%). The discovered novel methodology involve
- Ahmed, Faiz,Rauf, Abdul,Sharif, Ahsan,Ahmad, Ejaz,Arshad, Muhammad,Esposito, Breno Pannia,Kaneko, Telma Mary,Qureshi, Ashfaq Mahmood
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p. 761 - 772
(2018/07/15)
-
- Composition for trichogenousness
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The present invention relates to novel barbiturate and thiobarbiturate derivatives and a composition for promoting hair growth using the same. According to the present invention, the barbiturate and thiobarbiturate derivatives, in an animal model, have shown to promote hair growth and have excellent effects on hair growth by promoting regulation of Wnt/andbeta;-catenin and hair growth factor signaling and suppressing mechanism of apoptosis. Accordingly, the barbiturate and thiobarbiturate derivatives of the present invention may be used as a composition for promoting hair growth.COPYRIGHT KIPO 2017
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Paragraph 0200-0206
(2017/08/08)
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- Succinimidinium hydrogensulfate ([H-Suc]HSO4) as an efficient ionic liquid catalyst for the synthesis of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione and pyrano-pyrimidinones derivatives
-
In this work, succinimidinium hydrogensulfate ([H-Suc]HSO4), a newly reported Br?nsted acidic ionic liquids is used as an efficient, homogeneous and reusable catalyst for the synthesis of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d]-pyrimidine dione derivatives. The products were formed in excellent yields over short reaction times and the catalyst can be reused several times without any appreciable loss in its activity.
- Goli-Jolodar, Omid,Shirini, Farhad,Seddighi, Mohadeseh
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p. 457 - 463
(2016/01/30)
-
- Succinimidinium N-sulfonic acid hydrogen sulfate as an efficient ionic liquid catalyst for the synthesis of 5-arylmethylene-pyrimidine-2,4,6-trione and pyrano[2,3-d]pyrimidinone derivatives
-
Succinimidinium N-sulfonic acid hydrogen sulfate ([SuSA-H]HSO4) as a new ionic liquid is prepared and characterized using a variety of techniques, including infrared spectra (FT-IR), 1H and 13C NMR, scanning electron microscopy, a mass spectra method, as well as by Hammett acidity function. The prepared reagent is efficiently able to catalyze the preparation of 5-arylmethylene-pyrimidine-2,4,6-triones via the condensation of aldehydes and barbituric acid. Further studies showed that the condensation of aldehydes with barbituric acid and malononitrile leading to pyrano[2,3-d]pyrimidinone derivatives can also be efficiently promoted in the presence of this reagent. The present methodology offers several advantages, including ease of the preparation and handling of the catalyst, simple and easy work-up, short reaction times, high yields of the products and recyclability of the catalyst.
- Abedini, Masoumeh,Shirini, Farhad,Mohammad-Alinejad Omran, Javad,Seddighi, Mohadeseh,Goli-Jolodar, Omid
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p. 4443 - 4458
(2016/07/06)
-
- DABCO-based ionic liquids: Green and recyclable catalysts for the synthesis of barbituric and thiobarbituric acid derivatives in aqueous media
-
A new and straightforward method for the synthesis of 5-arylidine barbituric and thiobarbituric acids through a reaction between barbituric acid and its thio-analogue with aldehydes using 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium dihydrogen sulfate ([DABCO](SO3H)2(HSO4)2) as an efficient catalyst has been reported. In this project, also the preparation of pyrano[2,3-d]-pyrimidinediones via the reaction of barbituric or thiobarbituric acid, malononitrile and aldehydes in the presence of this reagent and 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium chloride ([DABCO](SO3H)2(Cl)2) has been investigated. The structure of the products was characterized using IR, 1H NMR and 13C NMR spectroscopy. The present methodologies suggests several advantages such as ease of the preparation and handling of the catalysts, high yields, simple and green procedures, low cost, short reaction times, easy work-up and preformation of the reaction in water as a green solvent.
- Seyyedi, Narges,Shirini, Farhad,Nikoo Langarudi, Mohaddeseh Safarpoor
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p. 44630 - 44640
(2016/06/09)
-
- New compounds having skin whitening, antioxidant and PPAR activity, and medical use thereof
-
PURPOSE: A novel compound with skin whitening, antioxidation, and PPAR activation effects, and a medical use thereof are provided to be used for a pharmaceutical composition or a cosmetic product. CONSTITUTION: A compound is denoted by chemical formula 1. A skin whitening composition contains the compound as an active ingredient. An antioxidative composition for preventing or treating oxidative diseases contains the compound of chemical formula 1 as an active ingredient. The oxidative diseases are selected among skin aging, pigmentation, wrinkling, psoriasis, or eczema. The composition prevents or treats diseases which are regulated by PPAR(peroxisome proliferator-activated receptor) activity. The PPAR includes PPAR alpha or PPAR gamma.
- -
-
Paragraph 0155-0156
(2017/04/14)
-
- SHIKIMATE PATHWAY INHIBITORS AND THE USE THEREOF
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The present invention relates to methods of inhibiting shikimate pathway, comprising administering to a subject a pharmaceutically acceptable composition comprising a compound having a formula: or pharmaceutically acceptable salts thereof. The present invention also provides a synergistic antibacterial composition containing compound
- -
-
Paragraph 0041;0042
(2015/05/26)
-
- Effect of reaction parameters on the synthesis of 5-arylidene barbituric acid derivatives in ball mills
-
The influence of crucial reaction parameters on Knoevenagel condensation in planetary ball mills was investigated. Rotation frequency (νrot), milling ball diameter (dMB), milling ball filling degree (φMB), and beaker size
- Schmidt, Robert,Burmeister, Christine F.,Balá?, Matej,Kwade, Arno,Stolle, Achim
-
supporting information
p. 427 - 436
(2015/04/14)
-
- Bi-SO3H functionalized ionic liquid based on DABCO as a mild and efficient catalyst for the synthesis of 1,8-dioxo-octahydro-xanthene and 5-arylmethylene-pyrimidine-2,4,6-trione derivatives
-
1,8-Dioxo-octahydro-xanthenes are easily prepared via the condensation of aldehydes with 1,3-cyclohexadione and/or dimedone using N-sulfonated DABCO as a new and efficient catalyst. This reagent is also efficiently able to catalyze the condensation of aldehydes with barbituric acid leading to 5-arylmethylene-pyrimidine-2,4,6-triones. The structure of the products was characterized by their IR, 1H NMR, and 13C NMR spectroscopy. The present methodology offers several advantages such as ease of preparation and handling of the catalyst, high yields, simple and green procedure, low cost, short reaction times, easy work-up, and preformation of the reaction in the absence of solvent or in water as a green solvent.
- Shirini, Farhad,Langarudi, Mohaddeseh Safarpoor Nikoo,Seddighi, Mohadeseh,Jolodar, Omid Goli
-
p. 8483 - 8497
(2015/01/30)
-
- Anomalous reaction of hydrazine hydrate with 5-arylidene barbiturates: Formation of benzalazines
-
Reaction of 5-arylidene barbiturates (3a-i) with hydrazine hydrate resulted in the unusual formation of novel benzalazines (5a-i) in 70-90% yield rather than the expected pyrazole fused pyrimidines.
- Goudgaon,Upendar Reddy, Ch.,Patil, Sharanabasappa,Sheshikant
-
p. 277 - 282
(2019/01/21)
-
- NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
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Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.
- -
-
Paragraph 0139-0140
(2014/02/16)
-
- Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones
-
Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections - a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 μM with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals.
- Neumann, Donna M.,Cammarata, Amy,Backes, Gregory,Palmer, Glen E.,Jursic, Branko S.
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p. 813 - 826
(2014/01/23)
-
- Evaluation of michael-type acceptor reactivity of 5-benzylidenebarbiturates, 5-benzylidenerhodanines, and related heterocycles using NMR
-
Despite existing experimental and computational tools to assess the risk, the non-specific chemical modification of protein thiol groups remains a significant source of false-positive hits, particularly in academic drug discovery. Herein, we describe the
- Arsovska, Emilija,Trontelj, Jurij,Zidar, Nace,Tomai, Tihomir,Mai, Lucija Peterlin,Kikelj, Danijel,Plavec, Janez,Zega, Anamarija
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p. 637 - 644
(2014/12/11)
-
- Nuclear magnetic resonance and molecular modeling study of exocyclic carbon-carbon double bond polarization in benzylidene barbiturates
-
Benzylidene barbiturates are important materials for the synthesis of heterocyclic compounds with potential for the development of new drugs. The reactivity of benzylidene barbiturates is mainly controlled by their exocyclic carbon-carbon double bond. In this work, the exocyclic double bond polarization was estimated experimentally by NMR and correlated with the Hammett σ values of the aromatic ring substituents and the molecular modeling calculated atomic charge difference. It is demonstrated that carbon chemical shift differences and NBO charge differences can be used to predict their reactivity.
- Figueroa-Villar, J. Daniel,Vieira, Andreia A.
-
p. 310 - 317
(2013/03/13)
-
- CoFe2O4 nanoparticles: An efficient heterogeneous magnetically separable catalyst for "click" synthesis of arylidene barbituric acid derivatives at room temperature
-
A coprecipitation method was used to synthesize superparamagnetic CoFe 2O4 nanoparticles without using any capping agents/surfactants. The prepared nanoparticles were characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, X-ray diffraction, a vibrating sample magnetometer (VSM), N2 adsorption and thermogravimetric/differential thermal analysis/differential thermal gravimetry techniques. The synthesized spinel CoFe2O4 nanoparticles had an average size of 2-8 nm with a high surface area (140.9 m2/g). The field-dependent magnetization, demonstrated by VSM and saturation magnetization, was found to be 1.77 emu/g. An efficient method was used for the synthesis of arylidene barbituric acid derivatives using CoFe2O4 magnetic nanoparticles as a magnetically separable and reusable catalyst in aqueous ethanol. The attractive features of this synthetic protocol were very short reaction time, high yields, high turnover frequency, simple work-up procedure, economy, a clean reaction methodology, and chemoselectivity, as well as provision of an ecofriendly and green synthesis.
- Rajput, Jaspreet Kaur,Kaur, Gagandeep
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p. 1697 - 1704
(2013/10/21)
-
- New strategy for the synthesis of 5-Aryl-1H,1′H-spiro[furo[2,3-d] pyrimidine-6,5′-pyrimidine]2,2′,4,4′,6′(3H,3'H,5H) -pentaones and their sulfur analogues
-
Reaction of barbituric acid (BA), 1,3-dimethyl barbituric acid (DMBA) and 2-thiobarbituric acid (TBA) with cyanogen bromide and aldehydes in the presence of L-(+)-tartaric acid afforded a new route for the synthesis of stable heterocyclic 5-aryl-1H,1′H-spiro[furo[2,3-d]pyrimidine-6,5′- pyrimidine]2,2′,4,4′,6′(3H,3′H,5H)- pentaones which is a dimeric form of barbiturate (uracil and thiouracil derivative). In the reaction of 1,3-diethyl thiobarbituric acid (DETBA) the Knoevenagel condensation and then Michael adducts were obtained under the same condition. Structure elucidation is carried out by 1H NMR, 13C NMR, FT-IR and Mass analyses. Mechanism of the formation is discussed.
- Jalilzadeh, Mohammad,Pesyan, Nader Noroozi
-
experimental part
p. 3382 - 3388
(2012/01/19)
-
- Preparation and reactivity of 5-benzylidenebarbituric and 5-benzylidene-2-thiobarbituric acids
-
The reaction between barbituric acid or 2-thiobarbituric acid and different benzaldehydes, dependent upon the applied reaction conditions, selectively yields three different product types, i.e. 5-benzylidene(thio)barbituric acids II, symetric Michael addu
- Zidar, Nace,Kikelj, Danijel
-
experimental part
p. 151 - 157
(2012/04/17)
-
- Synthesis of New dihydropyrimido[4,5-b]quinolinetrione derivatives using a four-component coupling reaction
-
A convenient and one-pot method for the efficient synthesis of the novel 8,9-dihydro-8,8-dimethyl-5,10-diphenylpyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H, 7H,10H)-trione derivatives via a four-component condensation reaction of aldehydes, amines, dimedone, a
- Khalafi-Nezhad,Panahi
-
scheme or table
p. 984 - 992
(2011/05/02)
-
- Facile Knoevenagel and domino Knoevenagel/Michael reactions using gel-entrapped base catalysts
-
An efficient method for Knoevenagel condensation of arenecarbaldehydes with active methylene compounds such as barbituric acid and Meldrum's acid in the presence of gel-entrapped base catalysts is reported. The method has been extended to the one-pot synthesis of arylmethylene-bis[3-hydroxycyclohex-2-en-1- one] derivatives from dimedone (=5,5-dimethylcyclohexane-1,3-dione) and arenecarbaldehydes by using domino Knoevenagel/Michael reaction sequence. Copyright
- Shinde, Shital,Rashinkar, Gajanan,Kumbhar, Arjun,Kamble, Santosh,Salunkhe, Rajashri
-
experimental part
p. 1943 - 1951
(2012/01/04)
-
- Water-prompted synthesis of alkyl nitrile derivatives via Knoevenagel condensation and Michael addition reaction
-
A straightforward and efficient method for the synthesis of nitriles or β-cyanocarbonyls via Knoevenagel condensation and Michael addition reaction of a barbituric acid, aldehyde and sodium cyanide in water without using any catalyst or activation at 70 °C is reported. The Royal Society of Chemistry.
- Soleimani, Ebrahim,Khodaei, Mohammad Mehdi,Batooie, Nasim,Baghbanzadeh, Mostafa
-
experimental part
p. 566 - 569
(2011/05/03)
-
- Synthesis, characterization and catalytic activity of Ce1Mg xZr1-xO2 (CMZO) solid heterogeneous catalyst for the synthesis of 5-arylidine barbituric acid derivatives
-
A series of Ce1MgxZr1-xo2 (CMZO) mixed metal oxide with different molar ratio were prepared by simple co-precipitation method. The prepared materials were tested for their catalytic activity performance using Knoevenagel condensation of various aromatic aldehydes with barbituric acid under solvent-free condition in microwave. The best catalytic activity was obtained with CMZO (1:0.6:0.4). The synthesized materials were characterized by using XRD, FT-IR, SEM-EDS techniques.
- Rathod, Sandip B.,Gambhire, Anil B.,Arbad, Balasaheb R.,Lande, Machhindra K.
-
experimental part
p. 339 - 343
(2010/08/19)
-
- Nickel nanoparticles catalyzed knoevenagel condensation of aromatic aldehydes with barbituric acids and 2-thiobarbituric acids
-
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
-
experimental part
p. 104 - 110
(2010/11/05)
-
- 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
-
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
-
experimental part
p. 273 - 281
(2010/05/02)
-
- SiO2?12WO3?24H2O: A highly efficient catalyst for the synthesis of 5-arylidene barbituric acid in the presence of water
-
The condensation of aromatic aldehydes and barbituric acid catalyzed by SiO212WO324H2O in aqueous media at room temperature gave 5-arylidene barbituric acid in high yields with or without the use of ultrasound, providing a simple and efficient route to synthesis of these compounds.
- Li, Ji-Tai,Sun, Ming-Xuan
-
experimental part
p. 353 - 355
(2009/09/06)
-
- Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities
-
A series of novel 5-benzylidene barbiturate and thiobarbiturate derivatives were synthesized and evaluated as tyrosinase inhibitors and antibacterial agents. The results demonstrated that some compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC50 = 1.22 mM). Particularly, compounds 1a and 2a were found to be the most potent inhibitors with IC50 value of 13.98 μM and 14.49 μM, respectively. The inhibition mechanism study revealed that these compounds were irreversible inhibitors. The circular dichroism spectra indicated that these compounds induced conformational changes of mushroom tyrosinase upon binding. In addition, these compounds exhibited selectively antibacterial activity against Staphylococcus aureus. All these results suggested that further development of such compounds may be of interest.
- Yan, Qin,Cao, Rihui,Yi, Wei,Chen, Zhiyong,Wen, Huan,Ma, Lin,Song, Huacan
-
experimental part
p. 4235 - 4243
(2009/12/24)
-
- Synthesis of barbiturate-based methionine aminopeptidase-1 inhibitors
-
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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- A new and efficient method for the synthesis of 5-arylmethylene- pyrimidine2,4,6-trione under solvent and catalyst free conditions
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A new and efficient method has been developed for the synthesis of 5-arylmethylene-pyrimidine-2,4,6-trione without any catalyst and solvent under microwave irradiation. A number of condensation products are prepared in very short reaction time with high yields.
- Sanjeeva Reddy,Nagaraj,Jalapathi
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p. 660 - 663
(2008/09/18)
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- Reaction of hexahydropyirimidine-2,4,6-trione with naphthalen-2-amine and benzaldehydes
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Previously unknown 12-aryl-7,8,9,10,11,12-hexahydrobenzo[f]pyrimido[4,5-b] quinoline-9,11-diones were synthesized by three-component condensation of naphthalen-2-amine with substituted benzaldehydes and barbituric acid through intermediate 5-benzylidenebarbituric acids. Nauka/Interperiodica 2007.
- Kozlov,Basalaeva
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p. 432 - 438
(2007/10/03)
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- Efficient method for synthesis of the derivatives of 5-arylidene barbituric acid catalyzed by aminosulfonic acid with grinding
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Aminosulfonic acid is an environmentally friendly catalyst. Grinding a mixture of aromatic aldehydes, barbituric acid, and H2NSO 3H at room temperature (without any solvent) gave 5-arylidene barbituric acid in high yields, providing a simple and efficient route to synthesis of these compounds. Copyright Taylor & Francis Group, LLC.
- Li, Ji-Tai,Dai, Hong-Guang,Liu, Da,Li, Tong-Shuang
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p. 789 - 794
(2007/10/03)
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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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- Solvent-free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield
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Numerous Knoevenagel condensations of solid or liquid aromatic aldehydes are performed with four barbituric acids, Meldrum's acid, dimedone, cyanoacetamide, malodinitrile and methyl cyanoacetate in stoichiometric mixtures of the solids or of stoichiometri
- Kaupp, Gerd,Naimi-Jamal, M. Reza,Schmeyers, Jens
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p. 3753 - 3760
(2007/10/03)
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- Preparation of 5,5′-pyrilidene and 5,5′-quinolidene bis-barbituric acid derivatives
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NMR reaction following experiments were used to find optimal conditions for the barbituric acid double addition to aromatic and heteroaromatic carboxaldehydes. It was established that aromatic aldehydes with electron-donating substituents such as hydroxy, methoxy, and dimethylamino produce only the single addition barbituric acid adduct (barbituric acid benzylidenes). If these electron-donating substituents are transformed into electron-withdrawing substituents by virtue of protonation (NMe2 to NHMe2+) then the double barbituric acid adduct becomes the sole product of the reaction. This is also true regardless of the reaction media if strong electron-withdrawing substituents (such as a nitro group) are present. Considering that the reactive species for nitrogen containing aromatic heterocycles are actually the conjugated acids (electron deficient molecule) only the double barbituric acid adducts are isolated. All synthetic procedures presented are applicable to multi-gram scale preparations of double barbituric acid adducts.
- Jursic, Branko S.,Neumann, Donna M.
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p. 465 - 474
(2007/10/03)
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- One pot synthesis of barbiturates on reaction of barbituric acid with aldehydes under microwave irradiation using a variety of catalysts
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The condensation of barbituric acid with aldehydes under microwave irradiation in dry media has been investigated in the presence of NH 4OAc/AcOH (4/3, w/w) (41-54%), Montmorillonite K-10 (49-60%), Silica gel (52-63%), basic Al2O3 (56-67%), NaCl (57-69%), Montmorillonite KSF (62-70%), and KSF + NaCl (1:1, w/w) (70-89%).
- Dewan, Sharwan K.,Singh, Ravinder
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p. 3081 - 3084
(2007/10/03)
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- Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates
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Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate. If 5-benzylbarbiturate is the target product, then the first step includes the preparation of 5-benzylidene. Regardless of the nature of the first step, all reactions presented synthetic yields around 90% and isolation and purification involves only crystallization.
- Jursic, Branko S.,Stevens, Edwin D.
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p. 2203 - 2210
(2007/10/03)
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- A simple method for knoevenagel condensation of α,β-conjugated and aromatic aldehydes with barbituric acid
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Several aromatic and α,β-conjugated aromatic aldehydes were condensed with barbituric acid in methanol solution in the absence of acid or base as a catalyst, affording 5-ylidenebarbituric acid derivatives in almost quantitative yields.
- Jursic
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p. 655 - 657
(2007/10/03)
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