- A practical one-pot synthesis of 5-aryl-2-furaldehydes
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A useful one-pot synthesis of 5-aryl-2-furaldehydes via palladium-mediated Suzuki coupling of aryl halides with in situ generated 5-(diethoxymethyl)-2-furylboronic acid is described. The procedure has general applicability, delivers high yields, and is amenable to scale-up.
- McClure,Roschangar,Hodson,Millar,Osterhout
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- Carbon–Carbon Bond Formation for the Synthesis of 5-Aryl-2-Substituted Furans Catalyzed by K3[Fe(CN)6]
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An efficient method for the carbon–carbon bond formation at C-5 position of 2-substituted furans to provide a range of π-diverse 5-aryl-2-substituted furan derivatives in 58–80% yield has been reported. The method employs several advantages such as use of catalytic amount of K3[Fe(CN)6] under mild conditions and short reaction time with high yields. Also, a variety of anilines with a variety of functional groups can be employed for the synthesis of 5-aryl-2-substituted furans. Graphic Abstract: [Figure not available: see fulltext.]
- Ambika,Singh, Pradeep Pratap
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- 5-Aryl-2-furaldehydes in the synthesis of tetrahydropyrimidinones by Biginelli reaction
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5-Aryl-2-furaldehydes, obtained by furfural arylation with arenediazonium salts, react with ethyl acetoacetate or acetylacetone and (thio)- urea in the presence of FeCl3·6H2O as a catalyst. A series of ethyl 4-(5-aryl-2-furyl)-6-methyl-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine- 5-carboxylates was obtained.
- Vakhula, Andriy R.,Horak, Yuriy I.,Lytvyn, Roman Z.,Lesyuk, Alexandra I.,Kinzhybalo, Vasyl,Zubkov, Fedor I.,Obushak, Mykola D.
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p. 545 - 549
(2018/07/05)
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- Multicomponent one pot synthesis and characterization of novel 4-furyl-1,4-dihydropyridines
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A series of dihydropyridines were prepared from the multi-component reaction of 5-arylfuran-2-carbaldehydes, ethylacetoacetate and ammonium acetate. These compounds were characterized through elemental analysis and various spectroscopic techniques (FTIR, 1H NMR, 13C NMR and mass).
- Zafar, Ansa Madeeha,Aslam, Samina,Khakwani, Samia,Khan, Muhammad Naeem,Munawar, Munawar Ali,Khan, Misbahul Ain
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p. 735 - 741
(2017/02/10)
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- 2-Aminothiazolones as anti-hiv agents that act as gp120-cd4 inhibitors
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We report here the synthesis of 2-Aminothiazolones along with their biological properties as novel anti-HIV agents. Such compounds have proven to act through the inhibition of the gp120-CD4 protein-protein interaction that occurs at the very early stage of the HIV-1 entry process. No cytotoxicity was found for these compounds, and broad antiviral activities against laboratory strains and pseudotyped viruses were documented. Docking simulations have also been applied to predict the mechanism, at the molecular level, by which the inhibitors were able to interact within the Phe43 cavity of HIV-1 gp120. Furthermore, a preliminary absorption, distribution, metabolism, and excretion (ADME) evaluation was performed. Overall, this study led the basis for the development of more potent HIV entry inhibitors.
- Tiberi, Marika,Tintori, Cristina,Ceresola, Elisa Rita,Fazi, Roberta,Zamperini, Claudio,Calandro, Pierpaolo,Franchi, Luigi,Selvaraj, Manikandan,Botta, Lorenzo,Sampaolo, Michela,Saita, Diego,Ferrarese, Roberto,Clementi, Massimo,Canducci, Filippo,Botta, Maurizio
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supporting information
p. 3043 - 3052
(2014/06/09)
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- General synthetic approach towards annelated 3a,6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations
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An efficient and versatile one-pot synthesis of 3,6a-epoxyisoindoles annelated with oxazine, oxazole, thiazine, thiazole, pyrimidine fragments and with their benzoannelated analogues is presented. The method is based on tandem N-acylation/intramolecular cycloaddition (the intramolecular Diels-Alder reaction of furan, IMDAF) reaction between α,β-unsaturated acid anhydrides and α-furyl substituted azaheterocycles. The latter can be easily prepared by condensation of diverse furfurals and 1,2- or 1,3-N,X-binucleophiles (aminoalcohols, aminothiols, diamines). The observed IMDAF reaction is stereoselective: exo-adducts are formed exclusively with large prevalence of one of the diastereoisomers. In most cases, the condensation/N-acylation/IMDAF reaction sequence may be carried out via a one-pot domino protocol. The scope and limitations of the proposed approach are thoroughly investigated. The obtained Diels-Alder adducts are attractive and useful substrates for further transformations. Fused isoindoles can be prepared from them in one-step by aromatization of the 7-oxabicyclo[2.2.1]heptene ring. Other transformations, including halogenation, ring cleavage, and Wagner-Meerwein skeletal rearrangement, are also demonstrated. The spatial structures of the obtained compounds have been established by X-ray diffraction analyses.
- Zubkov, Fedor I.,Nikitina, Eugenia V.,Galeev, Timur R.,Zaytsev, Vladimir P.,Khrustalev, Victor N.,Novikov, Roman A.,Orlova, Daria N.,Varlamov, Alexey V.
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p. 1659 - 1690
(2014/02/14)
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- NOVEL RHODANINE DERIVATIVES, METHOD FOR PREPARING SAME, AND PHARMACEUTICAL COMPOSITION FOR THE PREVENTION OR TREATMENT OF AIDS CONTAINING THE RHODANINE DERIVATIVES AS ACTIVE INGREDIENTS
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Disclosed are novel rhodanine derivatives which are inhibitory of HIV activity. Also provided are a method for preparing the novel rhodanine derivatives, and a pharmaceutical composition for the prevention or treatment of AIDS containing the rhodanine der
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Paragraph 0030; 0031
(2013/05/09)
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- NOVEL RHODANINE DERIVATIVES, METHOD FOR PREPARING SAME, AND PAHRMACEUTICAL COMPOSITION FOR THE PREVENTION OR TREATMENT OF AIDS CONTAINING THE RHODANINE DERIVATIVES AS ACTIVE INGREDIENTS
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Disclosed are novel rhodanine derivatives which are inhibitory of HIV activity. Also provided are a method for preparing the novel rhodanine derivatives, and a pharmaceutical composition for the prevention or treatment of AIDS containing the rhodanine der
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Paragraph 0104; 0105
(2013/04/24)
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- Development of novel alkene oxindole derivatives as orally efficacious AMP-activated protein kinase activators
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Adenosine 5′-monophosphate-activated protein kinase (AMPK) is emerging as a promising drug target for its regulatory function in both glucose and lipid metabolism. Compound PT1 (5) was originally identified from high throughput screening as a small molecu
- Yu, Li-Fang,Li, Yuan-Yuan,Su, Ming-Bo,Zhang, Mei,Zhang, Wei,Zhang, Li-Na,Pang, Tao,Zhang, Run-Tao,Liu, Bing,Li, Jing-Ya,Li, Jia,Nan, Fa-Jun
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supporting information
p. 475 - 480
(2013/07/25)
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- Synthesis of novel arylfurfurylchalcones
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Various aryl furans-2-carbaldehyde chalcones with different acetophenones were prepared and characterized through their elemental analyses and spectroscopic techniques (FTIR, 1H NMR, 13C NMR and mass spectra).
- Aslam, Samina,Asif, Nadia,Khan, Muhammad Naeem,Khan, Misbahul Ain,Munawar, Munawar Ali,Nasrullah, Muhammad
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p. 7738 - 7742
(2013/09/23)
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- Mechanism of Meerwein arylation of furan derivatives
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Catalytic arylation of furan-2-carbaldehyde with arenediazonium salts was studied. The yields of 5-arylfuran-2-carbaldehydes were found to depend on the solvent, catalyst, and anion in the arenediazonium salt. Redox catalysis and generation of aryl radicals are not sufficient conditions for the reaction to occur. The reaction is successful only under conditions ensuring formation of complex intermediates. A mechanism involving two Cu2+ ? Cu + catalytic series and generation of furan-2-carbaldehyde was proposed.
- Obushak,Lesyuk,Gorak, Yu. I.,Matiichuk
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experimental part
p. 1375 - 1381
(2010/01/11)
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- Furan-2-ylmethylene thiazolidinediones as novel, potent, and selective inhibitors of phosphoinositide 3-kinase γ
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Class I phosphoinositide 3-kinases (PI3Ks), in particular PI3Kγ, have become attractive drug targets for inflammatory and autoimmune diseases. Here, we disclose a novel series of furan-2-ylmethylene thiazolidinediones as selective, ATP-competitive PI3Kγ i
- Pomel, Vincent,Klicic, Jasna,Covini, David,Church, Dennis D.,Shaw, Jeffrey P.,Roulin, Karen,Burgat-Charvillon, Fabienne,Valognes, Delphine,Camps, Montserrat,Chabert, Christian,Gillieron, Corinne,Fran?on, Bernard,Perrin, Dominique,Leroy, Didier,Gretener, Denise,Nichols, Anthony,Vitte, Pierre Alain,Carboni, Susanna,Rommel, Christian,Schwarz, Matthias K.,Rückle, Thomas
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p. 3857 - 3871
(2007/10/03)
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- Inhibitors of HCV NS5B polymerase. Part 1: Evaluation of the southern region of (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid
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A novel series of nonnucleoside HCV NS5B polymerase inhibitors were prepared from (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid, a high throughput screening lead. SAR studies combined with structure based drug design focusing on the southern heterobiaryl region of the template led to the synthesis of several potent and orally bioavailable lead compounds. X-ray crystallography studies were also performed to understand the interaction of these inhibitors with HCV NS5B polymerase.
- Pfefferkorn, Jeffrey A.,Greene, Meredith L.,Nugent, Richard A.,Gross, Rebecca J.,Mitchell, Mark A.,Finzel, Barry C.,Harris, Melissa S.,Wells, Peter A.,Shelly, John A.,Anstadt, Robert A.,Kilkuskie, Robert E.,Kopta, Laurice A.,Schwende, Francis J.
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p. 2481 - 2486
(2007/10/03)
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- Dantrolene analogues revisited: General synthesis and specific functions capable of discriminating two kinds of Ca2+ release from sarcoplasmic reticulum of mouse skeletal muscle
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The general synthesis of dantrolene analogues with various substituents on its phenyl ring has been developed via palladium-catalyzed cross-coupling reactions, the Stille or Suzuki reaction, as the key step. The effects of synthesized analogues have been evaluated by two kinds of Ca2+ release modes from sarcoplasmic reticulum (SR) of mouse skeletal muscle fibers based on: (1) the measurement of twitch contraction caused by the physiological Ca2+ release (PCR) of intact skeletal muscle and (2) the rate of Ca2+-induced Ca2+ release (CICR) in saponin-treated skinned muscle fibers. Although dantrolene, a lead compound, inhibits both twitch contraction and CICR, some structurally modified analogues exhibit one or the other of these effects. The methoxy congener, GIF-0185, potently inhibits the twitch contraction without affecting the CICR, while GIF-0166 and GIF-0248, the ortho-nitro regioisomer and ortho, ortho-dinitro substituted analogues, respectively, doubly potentiate the CICR exclusively.
- Hosoya, Takamitsu,Aoyama, Hiroshi,Ikemoto, Takaaki,Kihara, Yasutaka,Hiramatsu, Toshiyuki,Endo, Makoto,Suzuki, Masaaki
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p. 663 - 673
(2007/10/03)
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- Facile synthesis of 5-aryl-furan-2-aldehyde and 5-aryl-furan-2-carboxylic acid using ceric ammonium nitrate
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A new method for the synthesis of furan-2-carboxaldehyde and 5-(substituted-phenyl)-furan-2-carboxylic acids using ceric ammonium nitrate (CAN) is reported.
- Subrahmanya Bhat,Shivarama Holla
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p. 625 - 628
(2007/10/03)
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- Structure-activity relationships of novel anti-malarial agents. Part 4: N-(3-Benzoyl-4-tolylacetylaminophenyl)-3-(5-aryl-2-furyl)acrylic acid amides
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In a previous report, we have described novel anti-malarial compounds based on a 2,5-diaminobenzophenone scaffold. Here, we have invesigated acryloyl derivatives carrying a biaryl structure consisting of a terminal aryl residue and a central 2-furyl ring. Several compounds were obtained in the series of para-substituted phenylfurylacryloyl derivatives that displayed improved anti-malarial activity in comparison to earlier described derivatives. From the structure-activity relationships it can be deduced that there has to be a lipophilic moiety in the para-position of the terminal phenyl residue. Furthermore, there are indications that, alternatively, activity may benefit from the presence of a polar moiety with hydrogen bond acceptor properties.
- Wiesner, Jochen,Mitsch, Andreas,Wissner, Pia,Kraemer, Oliver,Jomaa, Hassan,Schlitzer, Martin
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p. 2681 - 2683
(2007/10/03)
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- 5-Phenyl-2-furamidines: A new chemical class of potential antidepressants
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A series of 5-phenyl-2-furamidines has been synthesized and evaluated for antidepressant activities. Substitution in the phenyl ring with a nitro (4) or an amino (12) group in the ortho-position resulted in an increase in antidepressant activity. Both 4 and 12 antagonized tetrabenazine-induced ptosis in rodents and inhibited norepinephrine (noradrenaline) uptake into crude synaptosomes of whole mouse brain at doses or concentrations comparable to those of the tricyclic antidepressants. However, these compounds did not possess the anticholinergic and antihistaminic activities common to tricyclic antidepressants. In addition, they lacked monoamine oxidase inhibitory activity. The 5-phenyl-2-furamidines represent a new chemical class of antidepressants and may be useful for depressive patients who cannot tolerate the compromising side effects of the tricyclic antidepressants and monoamine oxidase inhibitors.
- Pong,Pelosi Jr.,Wessels,Yu,Burns,White,Anthony Jr.,Ellis,Wright,White Jr.
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p. 1411 - 1416
(2007/10/02)
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