- Synthesis and anti-inflammatory activity of three nitro chalcones
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The aim of this study was to synthesize three nitro substituted chalcones and to evaluate their anti-inflammatory activity in the model of carrageenan induced edema in rats. The nitro chalcone were prepared by aldol condensation using of mechanical agitation and environmentally friendly solvents with 72-73% yields in approximately 2 h. The three structures were evaluated on biological activity at dose of 200 mg/kg and they showed anti-inflammatory protective effect by both oral and intraperitoneal administration, this effect was time dependent.
- Gomez-Rivera, Abraham,Aguilar-Mariscal, Hidemi,Romero-Ceronio, Nancy,Roa-De La Fuente, Luis F.,Lobato-Garcia, Carlos E.
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- Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N?C Cleavage
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Although cross-coupling reactions of amides by selective N?C cleavage are one of the most powerful and burgeoning areas in organic synthesis due to the ubiquity of amide bonds, the development of mechanochemical, solid-state methods remains a major challe
- Ma, Yangmin,Shao, Lei,Szostak, Michal,Wang, Ruihong,Zhang, Jin,Zhang, Pei
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supporting information
(2022/01/04)
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- Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation
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The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.
- Nicholson, Kieran,Langer, Thomas,Thomas, Stephen P.
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supporting information
p. 2498 - 2504
(2021/04/13)
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- Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC
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A mechanochemical van Leusen pyrrole synthesis with a base leads to 3,4-disubstitued pyrroles in moderate to excellent yields. The developed protocol is compatible with a range of electron-withdrawing groups and can also be applied to the synthesis of oxazoles. Attempts to mechanochemically convert the resulting pyrroles into porphyrins proved to be difficult.
- Bolm, Carsten,Molitor, Claude,Rissanen, Kari,Schumacher, Christian,Smid, Sabrina,Truong, Khai-Nghi
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p. 14213 - 14222
(2021/09/07)
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- Synthesis, characterization and structure–activity relationship of non-linear optical response of chalcone derivatives with in silico insights
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Fifteen chalcone derivatives having D–A–D, D–A–A and A–A–D architectures have been synthesized by Claisen–Schmidt condensation reaction and characterized by UV–Vis, IR, 1H-NMR, 13C-NMR and Mass spectrometry. In order to unambiguously establish the structure–activity relationship for the non-linear optical activity of these compounds, for the first time to our knowledge, we use the femtosecond degenerate four wave mixing (DFWM) technique to quantify and compare the third-order non-linear optical (NLO) activity of all the 15 compounds, under identical conditions. The second harmonics generation (SHG) efficiencies for all the compounds have also been evaluated using the Kurtz-Perry powder method. Among the compounds that we have synthesized here, the ones with A–A–D architecture show the highest NLO activity. Our results show that the NLO activity of a compound with A–A–D architecture can be further enhanced by incorporating a substituent with strong electron withdrawing ability on ring A and strong electron donating substituent on ring B. The results of the in silico studies that we have carried out correlate well with our experimental findings. The compounds (E)-3-(4-(dimethylamino)phenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-N(CH3)2–4′-NO2) and (E)-3-(4-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-MeO-4′-NO2) show the highest NLO activity among the compounds we have reported here. Graphical abstract: [Figure not available: see fulltext.]
- Rai, Prashant,Chettri, Prajal,Kar, Swayamsiddha,Nagar, Malhar Anupam,Srivastava, Shailesh,Golakoti, Nageswara Rao
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supporting information
p. 2603 - 2615
(2021/02/01)
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- Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles
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An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to be a good solvent for this reaction.
- Chen, De-Yin,Song, Shuai,Chen, Ling-Yan,Ren, Xinfeng,Li, Ya
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supporting information
(2021/03/01)
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- Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B
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A library of monosubstituted chalcones (1-17) bearing electron-donating and electron-withdrawing groups on both aromatic rings were selected. The cell viability on human tumor cell lines was evaluated first. The compounds unable to induce detectable cytotoxicity (1, 13, and 14) were tested using the monoamine oxidase (MAO) activity assay. Interestingly, they inhibit MAO-B, acting as competitive inhibitors, with 13 and 14 showing the best profiles. In particular, 13 exhibited a potency higher than that of safinamide, taken as a reference. Docking studies and crystallographic analysis showed that in human MAO-B 13 binds with the halogen-substituted aromatic ring in the entrance cavity, similar to safinamide, whereas 14 is accommodated in the opposite way. The main conclusion of this cell biology, biochemistry, and structural study is to highlights 13 as a chalcone derivative that is worth consideration for the development of novel MAO-B-selective inhibitors for the treatment of neurodegenerative diseases.
- Iacovino, Luca G.,Pinzi, Luca,Facchetti, Giorgio,Bortolini, Beatrice,Christodoulou, Michael S.,Binda, Claudia,Rastelli, Giulio,Rimoldi, Isabella,Passarella, Daniele,Di Paolo, Maria Luisa,Dalla Via, Lisa
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supporting information
p. 1151 - 1158
(2021/06/30)
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- Recyclable Copper Nanoparticles-Catalyzed Hydroboration of Alkenes and β-Borylation of α,β-Unsaturated Carbonyl Compounds with Bis(Pinacolato)Diboron
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Nano-ferrite-supported Cu nanoparticles (Fe-dopamine-Cu NPs) catalyzed anti-Markovnikov-selective hydroboration of alkenes with B2pin2 is reported under mild reaction conditions. This protocol can be applied to a broad range of substrates with high functional group compatibility. In addition, we demonstrated the use of Fe-dopamine-Cu NPs as a catalyst for the β-borylation of α,β-unsaturated ketones and ester, providing alkylboronate esters in up to 98% yield. Reuse of the magnetically recyclable catalyst resulted in no significant loss of activity in up to five reaction runs for both systems. (Figure presented.).
- Shegavi, Mahadev L.,Saini, Suresh,Bhawar, Ramesh,Vishwantha, Meghana Desai,Bose, Shubhankar Kumar
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supporting information
p. 2408 - 2416
(2021/03/16)
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- Novel nicotinonitrile-coumarin hybrids as potential acetylcholinesterase inhibitors: design, synthesis, in vitro and in silico studies
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Abstract: Alzheimer’s disease is a degenerative brain condition that is the leading cause of dementia affecting millions of people around the world. Therapeutic development has focused on the problem of the loss of basal forebrain cholinergic function, as it is the only evidence responsible for brain neurodegeneration in patients with Alzheimer’s disease. Several attempts to improve cholinergic neurotransmission have been investigated by minimizing synaptic degradation of acetylcholine using acetylcholinesterase inhibitors. In the current study, we explore the designing of a new series of nicotinonitrile-coumarin hybrids as potential acetylcholinesterase inhibitors. The new hybrids were prepared utilizing pyridine-2(1H)-thiones as starting precursors. The in vitro acetylcholinesterase (AChE) inhibitory activities were examined for the new nicotinonitrile-coumarin hybrid molecules, when compared with donepezil as a standard drug with IC50 of 14?nM. Coumarin derivative, linked to 6-(4-nitrophenyl)-4-phenylnicotinonitrile, showed more effective inhibitory activity than the reference donepezil with IC50 of 13?nM. The free radical-scavenging capabilities against DPPH of the new hybrid derivatives were screened. Additionally, their in vitro cytotoxic activities have been tested against various eukaryotic cells. Furthermore, docking study showed excellent interaction between nicotinonitrile-coumarin hybrids and AChE. Graphic abstract: [Figure not available: see fulltext.]
- Sanad, Sherif M. H.,Mekky, Ahmed E. M.
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p. 213 - 224
(2020/08/05)
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- Boosting the catalytic performance of zinc linked amino acid complex as an eco-friendly for synthesis of novel pyrimidines in aqueous medium
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Zinc linked amino acid complex, Zn(l-proline)2, is considered as a green catalyst for the synthesis of novel series of pyrimidine derivatives 5a–q. The pyrimidines 5a–q were prepared via two pathways: the first is a one-pot reaction of guanidines 3a–c with aromatic aldehyde 1 and acetophenones 2; and the second one is the reaction of guanidines 3a–c with different chalcones 4a–j in aqueous medium. The simplicity of the operation, the short reaction time, and the high efficiency (97%) are the main advantages of this protocol. Furthermore, the green aspects of this synthetic protocol were further investigated by examining the reusability of Zn(l-proline)2 complex throughout five consecutive cycles without a significant loss of catalytic activity. This new procedure has presented remarkable advantages in terms of safety, simplicity, stability, mild conditions, a short reaction time, excellent yields, and high purities without using any organic solvents.
- Ahmed, Eman A.,Soliman, Ahmed M.M.,Ali, Ali M.,Ali El-Remaily, Mahmoud Abd El Aleem Ali
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- Rapid umpolung Michael addition of isatin N, N ′-cyclic azomethine imine 1,3-dipoles with chalcones
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The umpolung Michael addition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones is reported. The reaction could be finished within a very short time (0.3-2 min), with 3,3-disubstituted oxindole derivatives obtained in moderate to excellent yields with promising dr values. Unusual Michael adducts were obtained in moderate to high yields (26-98%) with low to high diastereoselectivities (0.8: 1 to 8.5: 1 dr). All the synthesized compounds (3, 3′, 4, 5, 5′, 7, 7′, 9 and 9′) were well characterized by FTIR, NMR, and mass spectral analyses and further confirmed by the single-crystal X-ray diffraction analysis of compounds 3aa and 4n.
- Yue, Guizhou,Jiang, Dan,Dou, Zhengjie,Li, Sicheng,Feng, Juhua,Zhang, Li,Chen, Huabao,Yang, Chunping,Yin, Zhongqiong,Song, Xu,Liang, Xiaoxia,Wang, Xianxiang,Lu, Cuifen
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supporting information
p. 11712 - 11718
(2021/07/12)
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- Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates
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A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C-C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.
- Shao, Jiru,An, Caiyun,Wang, Sunewang R.
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p. 4030 - 4041
(2021/07/19)
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- Design, Synthesis, and Antimicrobial Evaluation of Novel [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazepine Derivatives
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Abstract: The title compounds,3,3′,3″,3′′′-[methylenebis(oxybenzene-5,1,3-triyl)]tetrakis(6,8-diaryl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepines), were synthesized startingfrom dimethyl 4-hydroxyisophthalate which was reacted with dibromomethane toobtain tetramethyl 5,5′-[methylenebis(oxy)]di(benzene-1,3-dicarboxylate). Thelatter was treated with excess hydrazine hydrate, and the resultingtetrahydrazide was converted to tetrakis-1,2,4-triazolyl derivative viacyclization with ethanolic potassium hydroxide, carbon disulfide, and hydrazinehydrate. In the final stage, cyclocondensation with substituted chalconesafforded the target products. The structure of the newly synthesized compoundswas confirmed by elemental analyses and FT-IR and NMR spectra, and theirantimicrobial activities against some bacterial and fungal strains wereestimated by the disc diffusion method.
- Ayyash
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p. 2165 - 2170
(2021/02/09)
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- Near-infrared photoactivatable nitric oxide donors with photoacoustic readout
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In this chapter, we motivate the need for photoactivatable NO donor molecules and give a brief survey of the existing chemical tools in the field. We then provide detailed protocols for the synthesis and validation of a near-infrared light-activated NO do
- Zhou, Effie Y.,Knox, Hailey J.,Reinhardt, Christopher J.,Partipilo, Gina,Chan, Jefferson
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p. 113 - 147
(2020/06/27)
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- Rapid abnormal [3+2]-cycloaddition of isatinN,N′-cyclic azomethine imine 1,3-dipoles with chalcones
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The rapid synthesis of novel dicyclic spiropyrrolidine was reported, using [3+2]-cycloaddition of isatinN,N′-cyclic azomethine imine 1,3-dipoles, generated from the condensation of substituted isatins and pyrazolidones, with chalcones in 2-5 min. The dicy
- Yue, Guizhou,Dou, Zhengjie,Zhou, Zexi,Zhang, Li,Feng, Juhua,Chen, Huabao,Yin, Zhongqiong,Song, Xu,Liang, Xiaoxia,Wang, Xianxiang,Rao, Hanbing,Lu, Cuifen
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supporting information
p. 8813 - 8817
(2020/06/08)
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- Synthesis and in vitro study of new coumarin derivatives linked to nicotinonitrile moieties as potential acetylcholinesterase inhibitors
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The appropriate pyridine-2(1H)-thiones were reacted with an equivalent amount of 5-(chloromethyl)-2-hydroxybenzaldehyde in ethanol in the presence of potassium hydroxide to give the corresponding 2-hydroxybenzaldehyde derivatives in excellent yields. The latter derivatives were taken as key synthons for the preparation of the target hybrids. Therefore, 2-hydroxybenzaldehydes were reacted with benzoylglycine in acetic anhydride in the presence of fused sodium acetate at 100°C for 6 hours to afford a new series of nicotinonitrile-coumarin hybrids. The in vitro acetylcholinesterase inhibitory activities were estimated for the new coumarins. The results were expressed as the inhibition percentage of the tested hybrids at concentration of 25 nM, compared to donepezil as a reference (inhibition percentage of 70.5). Coumarin hybrids linked to 6-(4-nitrophenyl) or 6-(4-chlorophenyl)-4-phenylnicotinonitrile exhibited more effective inhibitory activities than donepezil with inhibition percentages of 94.1 and 72.3, respectively. The new coumarins were tested for their free radical-scavenging capabilities against DPPH. Furthermore, some new coumarins were tested for in vitro cytotoxic activity against each MCF-10A, MCF-7, Caco2, and HEPG2. The new hybrids showed cytotoxicity in micromolar range (IC50 of 3.5-13.9 μM) against all tested cell lines. These results clearly demonstrated that the hybrids being tested are not cytotoxic at the concentration required to inhibit acetylcholinesterase effectively.
- Mekky, Ahmed E. M.,Sanad, Sherif M. H.
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p. 4278 - 4290
(2020/09/12)
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- Studies of NMR Chemical Shifts of Chalcone Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
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A series of the chalcone derivatives of the five-membered monoheterocyclic compounds, (E)-1-aryl-3-heteroarylpropen-1-ones, were prepared by aldol condensation of the corresponding aldehydes of thiophene, pyrrole, and furan with m- and p-substituted acetophenones. Similar condensation of the acetyl compounds of the heterocycles with m- and p-substituted benzaldehydes gave another series of the chalcone derivatives, (E)-1-heteroaryl-3-arylpropen-1-ones. The 13C chemical shift values (δC) of the chalcone derivatives were determined in order to find if they correlated with the Hammett σ values. A good correlation, especially for the β-C for both series, was found for the 13C chemical shift values (δC) of the chalcone derivatives with the Hammett σ values. The chemical shift values of the β-C of the heterocyclic compounds were plotted against those of the benzene derivatives. The resulting slopes were found to be close to the values of the aromaticity indices.
- Jeong, Eun Jeong,Lee, In-Sook Han
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p. 668 - 673
(2019/07/12)
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- Organocatalytic asymmetric vinylogous 1,4-addition of α,α-Dicyanoolefins to chalcones under a bio-based reaction media: Discovery of new Michael adducts with antiplasmodial activity
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The organocatalysed asymmetric vinylogous Michael addition of α,α-dicyanoolefins to α,β-unsaturated aldehydes and ketones have been reported in the last decade, however, chalcones have been poorly explored. Moreover, a considerable part of the publications in this theme still employs undesirable solvents, such as toluene and THF, with concerns related to health and environmental safety. We report herein the use of a bifunctional catalyst derived from a Cinchona alkaloid to perform the enantio- and diastereoselective Michael addition of α,α-dicyanoolefins to chalcones using 2-MeTHF as solvent. The Michael adducts were obtained in moderate to good yields and were evaluated for their antiplasmodial and cytotoxic activity.
- Martelli, Lorena S.R.,Vieira, Lucas C.C.,Paix?o, Márcio W.,Zukerman-Schpector, Julio,de Souza, Juliana O.,Aguiar, Anna Caroline C.,Oliva, Glaucius,Guido, Rafael V.C.,Corrêa, Arlene G.
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supporting information
p. 3530 - 3542
(2019/05/24)
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- Synthesis and characterization of co-doped fly ash catalyst for chalcone synthesis
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A series of solid base fly ash hybrid materials were synthesized by doping alkali, alkaline earth metals with nitrogen, separately using co-precipitation process, combined with surfactant incorporating method. The catalysts were characterized by X-ray diffraction, scanning electron microscopy, transmission electron microscopy, X-ray photoelectron spectroscopy and photoluminescence spectroscopy. Results revealed that the co-doped hybrid materials are highly stable with particle size in the range of 40-60 nm. The surface basicity of fly ash was upraised by increased hydroxyl content by doping with alkali, alkaline earth metals with nitrogen. The basicity of hybrid material was measured by liquid phase, solvent free, single step condensation of 4-chlorobenzaldehyde and acetophenone giving higher conversion rate and selectivity of desired product chalcone. This conversion showed that the fly ash based hybrid material has sufficient basic site, responsible for the catalytic activity.
- Ghoshir,Kande,Muley,Gambhire
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p. 2165 - 2172
(2019/09/03)
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- Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles
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An efficient synthesis of fully substituted 2,3-dihydropyrroles has been achieved in one step through the three-component reaction of amines, aromatic aldehydes and α-ketoamides. This atom-economical and catalyst-free reaction is highly stereoselective and generates underexplored heterocycles in a single step. These compounds were examined in an enzymatic assay that led to the identification of potent α-glucosidase inhibitors, thereby demonstrating the utility of this novel methodology in medicinal chemistry.
- Wang, Dong,Li, Linna,Feng, Hairong,Sun, Hua,Almeida-Veloso, Fabrice,Charavin, Marine,Yu, Peng,Désaubry, Laurent
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supporting information
p. 2775 - 2780
(2018/06/27)
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- Chalcone derivatives enhance ATP-binding cassette transporters A1 in human THP-1 macrophages
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Atherosclerosis is a process of imbalanced lipid metabolism in the vascular walls. The underlying pathology mainly involves the deposition of oxidized lipids in the endothelium and the accumulation of cholesterol in macrophages. Macrophages export excessive cholesterol (cholesterol efflux) through ATP-binding cassette transporter A1 (ABCA1) to counter the progression of atherosclerosis. We synthesized novel chalcone derivatives and assessed their effects and the underlying mechanisms on ABCA1 expression in macrophages. Human THP-1 macrophages were treated with synthetic chalcone derivatives for 24 h. In Western blot and flow cytometry analyses, a chalcone derivative, (E)-1-(3,4-diisopropoxyphenyl)-3-(4-isopropoxy-3-methoxyphenyl)prop- 2-en-1-one (1m), was observed to significantly enhance ABCA1 protein expression in THP-1 cells (10 μM, 24 h). Levels of mRNA of ABCA1 and liver X receptor alpha (LXRα) were quantified using a real-time quantitative polymerase chain reaction technique and were found to be significantly increased after treatment with the novel chalcone derivative 1m. Several microRNAs, including miR155, miR758, miR10b, miR145, miR33, and miR106b, which functionally inhibit ABCA1 expression were suppressed after treatment with 1m. Collectively, 1m increases ABCA1 expression in human THP-1 macrophages. The mechanisms involve the activation of the LXRα-ABCA1 pathway and suppression of certain microRNAs that regulate ABCA1 expression.
- Teng, I-Jou,Tsai, Min-Chien,Shih, Shao-Fu,Tsuei, Bi-Feng,Chang, Hsin,Chuang, Yi-Ping,Lin, Chin-Sheng,Chern, Ching-Yuh,Chen, Sy-Jou
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- Synthesis and evaluation of central antinociceptive activity of ring substituted chalcones; molecular docking studies with monoacylglycerol lipase (MAGL) enzyme
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Chalcones possess Michael acceptor property due to the presence of α,β-unsaturated enone moiety in their structure. In the present study, molecular docking was performed to predict binding affinity of ring substituted chalcones with Monoacylglycerol lipase (MAGL), a serine hydrolase enzyme which can inhibited by Michael acceptors such as maleimide derivatives. 3, 4-Dimethoxy derivative, 3 h with -44.45 kJmol-1 of interaction energy, exhibited highest binding affinity and formed Pi-Sulphur interactions with methionine-123 residue of MAGL enzyme. As MAGL is an emerging target for antinociceptive drug development, ring substituted chalcones were synthesized and evaluated for their central antinociceptive activity using tail immersion and hot plate methods. The results revealed that compound 3 h chalcone bearing methoxy groups at 3rd and 4th positions of phenyl ring exhibited good antinociceptive activity in both the models. Good correlation was observed between antinociceptive activity and binding affinity toward MAGL in case of compound 3 hour.
- Begum, Shaheen,Begum, Arifa,Koganti, Bharathi
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p. 1890 - 1897
(2018/09/18)
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- Intermolecular [2+2] photocycloaddition of chalcones with 2,3-dimethyl-1,3-butadiene under neat reaction conditions
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The intermolecular [2 + 2] photocycloaddition of chalcones with 2,3-dimethyl-1,3-butadiene under visible-light irradiation for the synthesis of cyclobutane derivatives has been developed. Without using any photosensitizer, metallic catalyst and solvent, the reaction proceeded with high regioselectivity and moderate to high stereoselectivity. Mild reaction conditions and no additives make the reaction easy to operate. Control experiments and density functional theory (DFT) computations demonstrated that the reaction takes place via visible-light activation of chalcones, which is different from the previously reported [2 + 2] cycloaddition of chalcones.
- Tang, Fang,Tang, Li,Guan, Zhi,He, Yan-Hong
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supporting information
p. 6694 - 6703
(2018/10/15)
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- N -Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts to Generate α,β-Unsaturated Ketones
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An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C-H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity of the vinyl transfer.
- Rajkiewicz, Adam A.,Kalek, Marcin
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p. 1906 - 1909
(2018/04/16)
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- A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water
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A novel, hydrophilic and recyclable methoxypolyethylene glycol (PEG)-modulated s-triazine-based multifunctional Schiff base/N,P-ligand L9 was prepared and used in Pd-catalyzed Heck-type carbonylative coupling reactions, affording diverse chalcone derivatives and 1,4-dicarbonyl esters in good yields.
- Gao, Pei-Sen,Zhang, Kan,Yang, Ming-Ming,Xu, Shan,Sun, Hua-Ming,Zhang, Jin-Lei,Gao, Zi-Wei,Zhang, Wei-Qiang,Xu, Li-Wen
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supporting information
p. 5074 - 5077
(2018/05/26)
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- Imidazole-triazine type compound and preparation method and application thereof
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The invention provides an imidazole-triazine type compound which is shown as the formula 3 in the description and a preparation method and application thereof. The method comprises the steps that a triazine compound and an alpha,beta-unsaturated ketone type compound are mixed and added into a solvent, under the existence of a metal copper catalyst and an oxidizing material, the mixed solution is stirred and reacts 5-20 hours under the temperature of 60-150 DEG C, after the reaction is finished, the reacted solution is subjected to post processing, and the imidazole-triazine type compound which is shown as the formula 3 is obtained; the metal copper catalyst is halogenide of the copper or a copper salt; the oxidizing material is a halogen elementary substance. The imidazole-triazine type compound can be applied to prepare antibacterial drugs or antibacterial agents, and the preferred antibacterial drugs are the drugs which inhibit activity of escherichia coli.
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Paragraph 0031; 0032; 0033; 0034; 0035; 0037
(2017/10/06)
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- Asymmetric synthesis of new γ-butenolides: Via organocatalyzed epoxidation of chalcones
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γ-Butenolides have been recognized as an important structural framework in a number of natural products and medicinally important agents. In this work we describe a new metal-free sequential strategy for the asymmetric synthesis of substituted γ-butenolides having epoxychalcones as the advanced intermediate. Using the optimized reaction conditions, we were able to carry out the three-step sequence, epoxidation, olefination and hydrolysis, with only one single chromatographic purification of the final product, furnishing new enantiomerically enriched γ-butenolides in moderate overall yield and good enantiomeric excess.
- Vieira, Lucas C. C.,Matsuo, Bianca T.,Martelli, Lorena S. R.,Gall, Mayara,Paix?o, Marcio W.,Corrêa, Arlene G.
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supporting information
p. 6098 - 6103
(2017/08/02)
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- CBr4 as a Halogen Bond Donor Catalyst for the Selective Activation of Benzaldehydes to Synthesize α,β-Unsaturated Ketones
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CBr4 has been employed as a halogen bond donor catalyst for the selective activation of aldehyde, to achieve an efficient solvent- and metal-free CC bond forming reaction in the presence of strong acid sensitive groups such as methoxy, cyanide, ester, and ketal for the synthesis of α,β-unsaturated ketones. This unique capability of CBr4 to act as a halogen bond donor has been explored and established using UV-vis as well as IR spectroscopy. Moreover, this unprecedented methodology enables the synthesis of the pharmaceutically important molecule licochalcone A.
- Kazi, Imran,Guha, Somraj,Sekar, Govindasamy
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supporting information
p. 1244 - 1247
(2017/03/14)
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- Bifunctional Thiourea-Catalyzed Stereoablative Retro-Sulfa-Michael Reaction: Concise and Diastereoselective Access to Chiral 2,4-Diarylthietanes
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Owing to the chiral recognition capacity of bifunctional thioureas, a stereoablative retro-sulfa-Michael reaction has been developed. Utilization of a biphasic system enabled us to render the process catalytic. The usefulness of this methodology was further illustrated by the diastereoselective synthesis of all possible stereoisomers of 2,4-diarylthiethanes.
- Bacsó, András,Szigeti, Mariann,Varga, Szilárd,Soós, Tibor
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p. 429 - 439
(2016/12/24)
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- An eco-friendly synthesis of 2-pyrazoline derivatives catalysed by CeCl 3· 7 H 2O
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Abstract: 1,3,5-triaryl-2-pyrazoline derivatives were synthesised by a condensation reaction between chalcones and phenyl hydrazine using cerium chloride heptahydrate as a catalyst. All these reactions were carried out in ethyl lactate (70%) as a green solvent. Easy and efficient work up, recyclability of solvent and catalyst are the key merits of this protocol. Graphical Abstract:: SYNOPSIS A facile protocol for the synthesis of 1,3,5-triaryl-2-pyrazolines is described. The solvent ethyl lactate, obtained from renewable sources, is biodegradable. The catalyst CeCl 3· 7 H 2O is a water-tolerant Lewis acid with low toxicity. Easy and clean work up, recyclable solvent and catalyst are merits of the protocol. The reaction works well for all systems giving good yields of the desired products.[Figure not available: see fulltext.].
- Bhat, Prabhat,Shridhar, Gomathi,Ladage, Savita,Ravishankar, Lakshmy
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p. 1441 - 1448
(2017/09/25)
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- Chloramphenicol base chemistry. Part 11: chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones
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The first chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones is reported. The Michael adducts were obtained in good to excellent yields (up to 98% yield) and enantioselectivities (up to 94% ee). This reaction has a broad substrate scope to various α,β-unsaturated ketones. With this in mind, this methodology was successfully applied to the synthesis of a chiral piperidone, an advanced building block for dihydropyridinone P2X7 receptor antagonists.
- Yan, Linjie,Wang, Haifeng,Xiong, Fangjun,Tao, Yuan,Wu, Yan,Chen, Fener
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p. 921 - 929
(2017/07/11)
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- Synthesis, carbonic anhydrase I and II inhibition studies of the 1,3,5-trisubstituted-pyrazolines
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4-(3-(4-Substituted-phenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl) benzenesulfonamides (9–16) were successfully synthesized and their chemical structures were confirmed by 1H NMR, 13C NMR, and HRMS spectra. Carbonic anhydrase I and II inhibitory effects of the compounds were investigated. Ki values of the compounds were in the range of 316.7 ± 9.6–533.1 ± 187.8 nM towards hCA I and 412.5 ± 115.4–624.6 ± 168.2 nM towards hCA II isoenzymes. While Ki values of the reference compound Acetazolamide were 278.8 ± 44.3 nM and 293.4 ± 46.4 nM towards hCA I and hCA II izoenzymes, respectively. Compound 14 with bromine and compound 13 with fluorine substituents can be considered as the leader compounds of the series because of the lowest Ki values in series to make further detailed carbonic anhydrase inhibiton studies.
- Gul, Halise Inci,Mete, Ebru,Taslimi, Parham,Gulcin, Ilhami,Supuran, Claudiu T.
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p. 189 - 192
(2017/11/21)
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- Quest for Efficient Catalysts based on Zinc tert-Butyl Peroxides for Asymmetric Epoxidation of Enones: C2- vs C1-Symmetric Auxiliaries
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Zinc tert-butyl peroxide-based catalysts for the asymmetric epoxidation of enones using tert-butyl hydroperoxide as an oxidant have been developed. A comparative study of chiral monoanioninc N,N′-bidentate ligands, C2-symmetric bisoxazolinates and C1-symmetric enaminooxazolinates, revealed excellent performance of C1-symmetric auxiliary ligands on catalytic asymmetric epoxidation of enones (up to 96% yield, 91% ee).
- Raheem Keeri, Abdul,Justyniak, Iwona,Jurczak, Janusz,Lewiński, Janusz
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supporting information
p. 864 - 868
(2016/04/05)
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- The Complete Mechanism of an Aldol Condensation
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Although aldol condensation is one of the most important organic reactions, capable of forming new C-C bonds, its mechanism has never been fully established. We now conclude that the rate-limiting step in the base-catalyzed aldol condensation of benzaldehydes with acetophenones, to produce chalcones, is the final loss of hydroxide and formation of the C=C bond. This conclusion is based on a study of the partitioning ratios of the intermediate ketols and on the solvent kinetic isotope effects, whereby the condensations are faster in D2O than in H2O, regardless of substitution.
- Perrin, Charles L.,Chang, Kuei-Lin
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p. 5631 - 5635
(2016/07/13)
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- The cascade synthesis of α,β-unsaturated ketones via oxidative C-C coupling of ketones and primary alcohols over a ceria catalyst
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We herein report the oxidative C-C coupling of ketones and primary alcohols to produce α,β-unsaturated ketones in the absence of base additives. This cascade synthetic reaction was conducted at 150 °C in 12 h using a heterogeneous CeO2 catalyst. The conversion of acetophenone reached 74% with 89% selectivity to chalcone. A correlation between the CeO2 crystal plane and catalytic performance is established as the catalytic activities decrease in the sequence of (110) > (111) > (100). Characterization using Raman spectroscopy, CO2 temperature-programmed desorption (CO2-TPD), and in situ active site-capping tests has shown that the unusual catalysis of the CeO2 catalyst is attributed to the coexistence of basic and redox active sites. These sites synergistically catalyze the oxidation of alcohols to aldehydes and the aldol condensation to ketones. Moreover, the CeO2 catalyst can be reused several times after calcination to remove the surface-adsorbed substances.
- Zhang, Zhixin,Wang, Yehong,Wang, Min,Lu, Jianmin,Zhang, Chaofeng,Li, Lihua,Jiang, Jingyang,Wang, Feng
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p. 1693 - 1700
(2016/04/05)
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- Synthesis of α,β-unsaturated ketones from alkynes and aldehydes over Hβ zeolite under solvent-free conditions
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A facile Hβ zeolite-catalyzed strategy has been successfully developed for the synthesis of α,β-unsaturated ketones from alkynes and aldehydes under solvent-free conditions. The reaction proceeds via tandem hydration/condensation of alkynes with aldehydes to afford a range of α,β-unsaturated carbonyls in good to excellent yields. This journal is.
- Mameda, Naresh,Peraka, Swamy,Kodumuri, Srujana,Chevella, Durgaiah,Banothu, Rammurthy,Amrutham, Vasu,Nama, Narender
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p. 58137 - 58141
(2016/07/07)
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- A new solid acid catalyst FeCl3/bentonite for aldol condensation under solvent-free condition
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For the first time, a new solid acid catalyst has been used for the synthesis of aryl chalcones under solvent free conditions. A simple method (solid dispersion method) has been adopted for the synthesis of FeCl3/bentonite. The prepared catalyst has been characterized by different characterization techniques. A series of E-1-(substituted phenyl)-3-(1-pyrenyl)-2-propen-1-ones have been synthesized using FeCl3/bentonite under microwave-assisted solvent-free conditions. The yields are in the range from 80 to 88%. All the synthesized chalcones have been characterized by their physical constants, analytical, IR, 1H and 13C NMR spectral data. This catalyst can be reused for further runs (after fifth cycle) without decrease in activity. This catalyst gives excellent yields and is inexpensive and easily recyclable for this reaction.
- Muthuvel,Dineshkumar,Thirumurthy,Rajasri,Thirunarayanan
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p. 252 - 260
(2017/01/18)
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- Synthesis, cyclooxygenase inhibition and anti-inflammatory evaluation of new 1,3,5-triaryl-4,5-dihydro-1H-pyrazole derivatives possessing methanesulphonyl pharmacophore
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A new series of 1,3,5-triaryl-4,5-dihydro-1H-pyrazole derivatives 13a–p were synthesized via aldol condensation of 3/4-nitroacetophenones with appropriately substituted aldehydes followed by cyclization of the formed chalcones with 4-methanesulfonylphenylhydrazine hydrochloride. All the synthesized compounds were evaluated for their cyclooxygenase (COX) inhibition, anti-inflammatory activity and ulcerogenic liability. All compounds were more potent inhibitors for COX-2 than COX-1. While most compounds showed good anti-inflammatory activity, compounds 13d, 13f, 13k and 13o were the most potent derivatives (ED50 = 66.5, 73.4, 79.8 and 70.5 μmol/kg, respectively) in comparison with celecoxib (ED50 = 68.1 μmol/kg). Compounds 13d, 13f, 13k and 13o (ulcer index = 3.89, 4.86, 4.96 and 3.92, respectively) were 4–6 folds less ulcerogenic than aspirin (ulcer index = 22.75) and showed approximately ulceration effect similar to celecoxib (ulcer index = 3.35). In addition, molecular docking studies were performed for compounds 13d, 13f, 13k and 13o inside COX-2 active site which showed acceptable binding interactions (affinity in kcal/mol ?2.1774, ?6.9498) in comparison with celecoxib (affinity in kcal/mol ?6.5330).
- Abdellatif, Khaled R. A.,Elsaady, Mohammed T.,Abdel-Aziz, Salah A.,Abusabaa, Ahmed H. A.
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p. 1545 - 1555
(2016/10/09)
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- Rational design, synthesis and in vitro evaluation of allylidene hydrazinecarboximidamide derivatives as BACE-1 inhibitors
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BACE-1 (β-secretase) is considered to be one of the promising targets for treatment of Alzheimer's disease as it catalyzes the rate limiting step of Aβ-42 production. Herein, we report a novel class of allylidene hydrazinecarboximidamide derivatives as moderately potent BACE-1 inhibitors, having aminoguanidine substitution on allyl linker with two aromatic groups on either side. A library of derivatives was designed based on the docking studies, synthesized and evaluated for BACE-1 inhibition in vitro. The designed ligands displayed interactions with the catalytic aspartate dyad through guanidinium functionality. Further, the aromatic rings placed on either side of the linker occupied S1 and S3 active site regions contributing to the activity. These ligands were also predicted to follow Lipinski rule and cross blood brain barrier. Compound 2.21, having high docking score, was found to be most active with IC50 of 6.423 μM indicating good correlation with docking prediction.
- Jain, Priti,Wadhwa, Pankaj K.,Rohilla, Shilpa,Jadhav, Hemant R.
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supporting information
p. 33 - 37
(2015/12/18)
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- 2-Oxindole Acts as a Synthon of 2-Aminobenzoyl Anion in the K2CO3-Catalyzed Reaction with Enones: Preparation of 1,4-Diketones Bearing an Amino Group and Their Further Transformations
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A convenient approach for the synthesis of 1,4-diketones bearing an amino group has been developed through the K2CO3-catalyzed reaction of 2-oxindoles with enones with the assistance of atmospheric O2 via sequential Michael addition-oxidation-ring-cleavage process. The further intramolecular reaction leads to the formation of benzoazepinone, quinoline, and 3-oxindole derivatives.
- Miao, Chun-Bao,Zeng, Yu-Mei,Shi, Tong,Liu, Rui,Wei, Peng-Fei,Sun, Xiao-Qiang,Yang, Hai-Tao
-
-
- Effects of substituents on NMR chemical shifts and mass fragmentation patterns of 1-aryl-3-phenylpropanes
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The 1H and 13C chemical shifts and the mass spectral fragmentation patterns of 1-aryl-3-phenylpropanes with m- or p-substituents (H, NO2, Br, Cl, OCH3, CH3) were studied. The electronic effects of the substi-tuents seemed to be transmitted by the through-space as well as by a through-bond mechanism, resulting in an inverse correlation in the plot of the chemical shift values of i-C vs. the Hammett σ values. The mass spectra showed the substituted benzyl fragments as the base peaks when the substituents were electron donating, whereas the benzyl fragment was observed as the base peaks with the electron-withdrawing substituents.
- Jeong, Eun Jeong,Lee, In-Sook Han
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p. 538 - 543
(2016/04/26)
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- Iodine-promoted oxidative coupling reaction: a simple and efficient process to access imidazo[1,2-a]pyridines from 2-aminopyridines and chalcones
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A unique and efficient approach has been developed for the synthesis of substituted imidazo[1,2-a]pyridines with aminopyridines and chalcones via a one-pot I2-induced aerobic oxidative coupling. The reported reaction proceeded though a tandem Michael addition followed by an intramolecular oxidative amination with high regioselectivity, yields and good functional group tolerance.
- Xing, Meng-Ming,Xin, Ming,Shen, Chao,Gao, Jian-Rong,Jia, Jian-Hong,Li, Yu-Jin
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supporting information
p. 4201 - 4204
(2016/07/06)
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- Synthesis of some novel 5,7-disubstituted-2-phenyl-5H-[1,3,4]thiadiazolo [3,2-a]pyrimidine derivatives and evaluation of their biological activity
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Background: In the present study, a series of 5,7-disubstituted-2-phenyl-5H-[1,3,4] thiadiazolo[3,2-a]pyrimidine derivatives have been reported. The title compounds were synthesized by the reaction of substituted chalcones with 5-phenyl-1,3,4-thiadiazol-2-amine in n-butanol. Methods: All reactions were performed at reflux temperature and the synthesized compounds were characterized by IR, NMR and Mass spectroscopic techniques. Results: The synthesized compounds were screened for their antimicrobial and antioxidant activities. The compounds displayed significant antimicrobial and antioxidant activities. Additionally, the selected compounds were screened for in silico molecular docking studies. Conclusion: In the present work, we have reported an efficient method for the synthesis of some new 5,7-disubstituted-2-phenyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidine derivatives. Collectively, all the current computational insights support the in vitro observations seen for antimicrobial and antioxidant agents. Further, the pyrimidine derivatives might act as potential specific inhibitors of G6P synthase thereby facilitating its biological activities. From the activity results, it has been concluded that among the studied compounds, compounds 5b, 5d, 5e, 5g, 5i, 5m and 5n could serve as potential antimicrobial and antioxidant agents.
- Venkatesh, Talavara,Bodke, Yadav D.,Joy, Nibin M.,Vinoda,Shiralgi, Yallappa,Dhananjaya
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p. 661 - 671
(2017/01/13)
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- Synthetic and mechanistic studies on the solvent-dependent copper-catalyzed formation of indolizines and chalcones
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Copper nanoparticles supported on activated carbon have been found to catalyze the multicomponent synthesis of indolizines from pyridine-2-carbaldehyde derivatives, secondary amines, and terminal alkynes in dichloromethane; in the absence of solvent, howe
- Albaladejo, María José,Alonso, Francisco,González-Soria, María José
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p. 3446 - 3456
(2015/06/16)
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- Efficient synthesis of 2,4-diaryl hexahydroquinoline-5-one derivatives in the presence of triethylamine
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Abstract A convenient and efficient protocol for the synthesis of 2,4-diaryl hexahydroquinoline-5-one derivatives has been accomplished by a three-component reaction of 1,3-diaryl-2-propen-1-ones, dimedone and ammonium acetate catalyzed by triethylamine under solvent-free conditions. The simple experimental procedure, use of an inexpensive catalyst, short reaction times, and excellent yields make this procedure facile, practical, and sustainable.
- Karimi-Jaberi, Zahed,Azadi, Maryam
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p. 6741 - 6747
(2015/02/19)
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- Iodine-Promoted Construction of Polysubstituted 2,3-Dihydropyrroles from Chalcones and β-Enamine Ketones (Esters)
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A novel approach for the synthesis of a variety of polysubstituted trans-2,3-dihydropyrroles from a wide range of chalcones and β-enamine ketones (esters) via iodine-promoted tandem Michael/cyclization sequence has been developed, affording the desired products in moderate to excellent yields. This methodology is a highly efficient, convenient way to access functionalized 2,3-dihydropyrroles from readily accessible substrates under mild reaction conditions.
- Li, Yujin,Xu, Hui,Xing, Mengming,Huang, Fang,Jia, Jianhong,Gao, Jianrong
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supporting information
p. 3690 - 3693
(2015/08/18)
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- Efficient Protocol for the Synthesis of Novel Spiro[acenaphthylene-1,2′-pyrrolidin]-2-one Compounds
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An efficient catalyst-free synthesis of 3′-benzoyl-4′,5′-diphenyl-2H-spiro[acenaphthylene-1,2′-pyrrolidin]-2-one derivatives via one-pot 1,3-dipolar cycloaddition of acenaphthenequinone, arylmethyl amines, and chalcones with high regioselectivity is described. The structure of the cycloadducts were characterized by infrared, high-resolution mass spectrometry (electrospray ionization), 1H NMR, and 13C NMR spectra, and the structure of 4a was confirmed using x-ray single-crystal structure analysis.
- Lin, Yan,Fu, Zhijie,Shen, Tianhua,Che, Fengfeng,Song, Qingbao
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supporting information
p. 2188 - 2194
(2015/09/22)
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- Synthesis and anti-inflammatory evaluation of new 1,3,5-triaryl-4,5-dihydro-1H-pyrazole derivatives possessing an aminosulphonyl pharmacophore
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A novel series of 2-pyrazoline derivatives 13a-l was synthesized via aldol condensation of 4-substituted acetophenones with appropriately substituted aldehydes followed by cyclization of the formed chalcones with 4-hydrazinobenzenesulfonamide hydrochlorid
- Abdellatif, Khaled R. A.,Abdelgawad, Mohamed A.,Elshemy, Heba A. H.,Alsayed, Shahinda S. R.,Kamel, Gehan
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p. 1932 - 1942
(2015/11/24)
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- Montmorillonite clay-promoted, solvent-free cross-aldol condensations under focused microwave irradiation
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An environmentally benign, clean and general protocol was developed for the synthesis of aryl and heteroaryl trans-chalcones. This method involved solvent-free reaction conditions under microwave irradiation in the presence of a clay-based catalyst, and afforded the target compounds in good yields and short reaction times. Furthermore, the same conditions allowed the synthesis of symmetrical, diarylmethylene-a,a-unsaturated ketones from aromatic aldehydes and ketones.
- Rocchi, Damiano,Gonzalez, Juan F.,Menendez, J. Carlos
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supporting information
p. 7317 - 7326
(2014/07/08)
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- Nano titania-supported sulfonic acid: An efficient and reusable catalyst for a range of organic reactions under solvent free conditions
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Nano titania-supported sulfonic acid (n-TSA) has been easily prepared from the reaction of nano titania (titanium oxide) with chlorosulfonic acid as sulfonating agent and characterized by the FT-IR spectroscopy, scanning electron microscopy (SEM), X-ray diffraction (XRD) and thermal gravimetric analysis (TGA). The catalytic activity of n-TSA was investigated in the synthesis of important organic derivatives such as pyrimidones, benzothiazoles and chalcones. All of the reactions are very fast and the yields are good to excellent. The catalyst was easily separated and reused for several runs without appreciable loss of its catalytic activity.
- Rahmani, Salman,Amoozadeh, Ali,Kolvari, Eskandar
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p. 184 - 188
(2014/11/08)
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- Iron-catalyzed aerobic oxidative aromatization of 1,3,5-trisubstituted pyrazolines
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A simple and high yielding method for the synthesis of tri-substituted pyrazoles via iron(III) catalyzed aerobic oxidative aromatization of pyrazolines has been reported. The process demonstrates a variety of functional group tolerance.
- Ananthnag, Guddekoppa S.,Adhikari, Adithya,Balakrishna, Maravanji S.
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p. 240 - 243
(2013/12/04)
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