- Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite
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Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.
- Zhu, Guanxin,Duan, Zheng-Chao,Zhu, Haiyan,Ye, Dongdong,Wang, Dawei
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supporting information
p. 266 - 270
(2021/08/06)
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- Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water
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A variety of chalcones were synthesized in good yields by the activated charcoal-mediated aldol reactions between benzaldehydes and acetophenones catalyzed by NaOH in water. 2,6-Bis((E)-benzylidene)cyclohexan-1-ones were prepared by the aldol reactions between benzaldehydes and cyclohexanone. Activated charcoal could be recycled five times without the significant decrease of yields.
- Tanemura, Kiyoshi,Rohand, Taoufik
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supporting information
(2021/02/27)
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- Crystal engineering with pyrazolyl-thiazole derivatives: Structure-directing role of π-stacking and σ-hole interactions
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The synthesis and X-ray characterization of 1-(2-(3-(4-bromophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazol-5-yl)ethanone (7), ethyl 2-(5-(4-bromophenyl)-3-(4-chlorophenyl)-4,5-dihydropyrazol-1-yl)thiazole-4-carboxylate (8) and 2-(5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-N′-(2-hydroxy-3-methoxybenzylidene)thiazole-4-carbohydrazide (10) are described in this manuscript. The structure-directing role of a variety of noncovalent interactions has been analyzed energetically using DFT calculations and Hirshfeld surface analysis. Moreover, the existence and importance of halogen and chalcogen bonding interactions have been analyzed by using the quantum theory of atoms in molecules and the noncovalent interaction index (NCIplot).
- Ahmed, Muhammad Naeem,Madni, Murtaza,Anjum, Shaista,Andleeb, Saiqa,Hameed, Shahid,Khan, Abdul Majeed,Ashfaq, Muhammad,Tahir, Muhammad Nawaz,Gil, Diego M.,Frontera, Antonio
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p. 3276 - 3287
(2021/05/17)
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- Iridium and copper supported on silicon dioxide as chemoselective catalysts for dehydrogenation and borrowing hydrogen reactions
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High active ligand usually plays an important role during catalysis and synthesis chemistry. A new and efficient benzotriazole-pyridinyl-silane ligand (BPS) was designed, and the corresponding iridium and copper catalysts were synthesized and thoroughly characterized by means of EDS, TEM, and XPS. The resulting iridium composite revealed excellent catalytic activity for the reaction of tert-butanesulfinamide with benzyl alcohols, while copper catalyst could realize the synthesis of unsaturated carbonyl compounds through the reaction of benzyl alcohols with ketones. This provided an efficient method for selective synthesis of unsaturated carbonyl compounds from benzyl alcohols and ketones in high yields with good recovery performance.
- Zhu, Guanxin,Duan, Zheng-Chao,Zhu, Haiyan,Qi, Minghui,Wang, Dawei
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- Potassium Natural Asphalt Sulfonate (K-NAS): Synthesis and characterization as a new recyclable solid basic nanocatalyst and its application in the formation of carbon–carbon bonds
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In this research, we synthesized and characterized a new heterogeneous basic nanocatalyst and its catalytic application was studied in the Claisen-Schmidt and Knoevenagel condensations. In order to prepare this nanocatalyst, first, the Iranian natural asphalt was sulfonated with the concentrated sulfuric acid and then, converted to the potassium natural asphalt sulfonate (K-NAS). In order to characterization of the nanocatalyst, used of FT-IR spectroscopy, scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), X-ray diffraction (XRD), inductively coupled plasma (ICP) and thermogravimetric analysis (TGA) techniques. This new basic heterogeneous nanocatalyst have advantages such as being eco-friendly, huge specific surface area, high reactivity and recyclability.
- Falah, Saeid,Soleiman-Beigi, Mohammad,Kohzadi, Homa
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- A Convenient One-Pot Synthesis of Chalcones and Their Derivatives and Their Antimicrobial Activity
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Abstract: A series of chalcones were synthesized by base-catalyzed Clasien-Schmidtcondensation of substituted benzaldehydes and substituted acetophenones at roomtemperature. The addition of hydrazine hydrate and hydroxylamine hydrochlorideacross the double bond of the obtained chalcones gave pyrazole and isoxazolederivatives, respectively. All the synthesized compounds were characterized by1H and 13C NMR andFT-IR spectroscopy and screened for their in vitro antimicrobial activityagainst two bacterial strains, Pseudomonasaeruginosa and Pseudomonasoryzihabitans using Ciprofloxacin as standard drug.1-(2-Methoxyphenyl)-3-phenylprop-2-en-1-one and1-(4-chlorophenyl)-3-phenylprop-2-en-1-one showed significant activity againstboth bacterial strains and hence proved to be potent antimicrobialagents.
- Salotra,Utreja,Sharma
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p. 2207 - 2211
(2021/02/09)
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- Tuning the Product Selectivity of the α-Alkylation of Ketones with Primary Alcohols using Oxidized Titanium Nitride Photocatalysts and Visible Light
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The direct α-alkylation of ketones with alcohol to synthesize important α-alkylated ketones and enones is an attractive procedure for C-C bond formation. High reaction temperatures are always needed for heterogeneous catalysis using non-noble metals, and switching product selectivity in one catalysis system remains a great challenge. In the present study, a visible-light-driven procedure for this reaction is proposed, using oxidized TiN photocatalysts under mild conditions, whereby the product selectivity can be well-tuned. Oxidized TiN photocatalysts with tunable surface N/O ratios were successfully synthesized through the facile and flexible thermal oxidation treatment of low-cost TiN nanopowder. The α-alkylation of acetophenone with benzyl alcohol to form the two important compounds chalcone and dihydrochalcone occurred even at room temperature and almost complete conversion was achieved at 100 °C under visible light. The proportion of the two products can be well-tuned by switching the surface N/O ratio of the synthesized photocatalysts. Visible light is demonstrated to affect the surface N/O ratio of the photocatalysts and contribute to tuning the product selectivity. Light intensity and action spectrum study proves that the generation of energetic charge carriers results in the observed activities under visible light, based on interband transitions of TiN or the ligand-to-metal charge transfer (LMCT) effect of the surface complex formed on TiO2. Thermal energy can be coupled with light energy within this photocatalytic system, which will facilitate the full use of solar energy. Different sequential reaction mechanisms on TiN and TiO2 are proposed to be responsible for the tunable product selectivity. The wide reaction scope, the fine conversion at a low light intensity, and the favorable reusability of photocatalysts prove the great application potential of this visible-light-driven procedure for the α-alkylation of ketones with primary alcohols.
- Li, Peifeng,Su, Haijia,Xiao, Gang,Zhao, Yilin
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p. 3640 - 3649
(2020/04/09)
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- Hydroxyl- and Halogen-containing Chalcones for the Inhibition of LPS-stimulated ROS Production in RAW 264.7 Macrophages: Design, Synthesis and Structure–Activity Relationship Study
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Oxidative stress due to overproduction of reactive oxygen species (ROS) plays a major role in inflammation, cancer, and neurodegenerative disorders. In this study, 60 chalcone derivatives with fluorine (F), trifluoromethyl (CF3), trifluoromethoxy (OCF3), chlorine (Cl), and bromine (Br) in ring A and with or without hydroxy (OH) in ring B were designed, synthesized, and screened for inhibitory activity against lipopolysaccharide (LPS)-stimulated ROS production in RAW 264.7 macrophages. Structure–activity relationship study revealed the importance of a hydroxyl moiety in ring B for enhancing inhibitory activity of ROS production. Furthermore, a hydroxyl group at the ortho-position is more essential for inhibition of ROS production followed by meta- and para-positions. Among all, compound 27 that contains para-chlorine moiety in ring A and ortho-hydroxy in ring B displayed the strongest inhibitory activity (IC50 = 3.42 μM) against LPS-stimulated ROS production in RAW264.7 macrophages.
- Shrestha, Aarajana,Shrestha, Aastha,Park, Pil-Hoon,Lee, Eung-Seok
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p. 729 - 734
(2019/07/19)
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- Naphtho[2,3-: B] furan-4,9-dione synthesis via palladium-catalyzed reverse hydrogenolysis
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A reverse hydrogenolysis process has been developed for two-site coupling of 2-hydroxy-1,4-naphthoquinones with olefins to produce naphtha[2,3-b]furan-4,9-diones and hydrogen (H2). The reaction is catalyzed by commercially available Pd/C without oxidants and hydrogen acceptors, thereby providing an intrinsically waste-free approach for the synthesis of functionalized and potentially biologically relevant naphtha[2,3-b]furan-4,9-diones.
- Li, Jimei,Zhang, Jie,Li, Mingfei,Zhang, Chenyang,Yuan, Yongkun,Liu, Renhua
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supporting information
p. 2348 - 2351
(2019/02/27)
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- Application of Polyphosphoric Acid-Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2-Acylpyrroles from Chalcones
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A metal-free approach for the synthesis of 2-acylpyrroles is reported in this paper. Synthesis of the target molecule started from chalcones and was carried out in two steps. Initial step involved the conversion of chalcones to corresponding 4-substituted-3-acylpyrroles by reaction with TosMIC. In the subsequent step, target molecules were obtained in modest to good yields by polyphosphoric acid-mediated acyl rearrangement of 3-acylpyrroles to their 2-acyl congeners. The crucial final step was amenable to diverse substitutions on pyrrole ring. Preliminary experiment for the determination of mechanism indicated the involvement of acylium ion.
- Kumar, Togiti Uday,Thigulla, Yadagiri,Rangan, Krishnan,Bhattacharya, Anupam
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supporting information
p. 1283 - 1290
(2019/03/07)
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- Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols
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The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.
- Zhang, Meng-Juan,Li, Hong-Xi,Young, David J.,Li, Hai-Yan,Lang, Jian-Ping
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supporting information
p. 3567 - 3574
(2019/04/14)
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- Copper-Promoted Oxidative Intramolecular C–H Amination of Hydrazones to Synthesize 1H-Indazoles and 1H-Pyrazoles Using a Cleavable Directing Group
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A facile and efficient synthesis of 1H-indazoles and 1H-pyrazoles through a copper-promoted oxidative intramolecular C–H amination of hydrazones using a cleavable directing group was developed. This reaction is characterized by its mild conditions, operational simplicity, readily available reagents, and excellent yields. A tentative mechanism for Cu-mediated C–H oxidative amination was proposed.
- Zhang, Guofu,Fan, Qiankun,Zhao, Yiyong,Ding, Chengrong
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supporting information
p. 5801 - 5806
(2019/08/02)
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- An improved synthesis of pyrido[2,3-: D] pyrimidin-4(1 H)-ones and their antimicrobial activity
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The screening of a small library of diverse chemical structures resulted in the identification of 2-thioxodihydropyrido[2,3-d]pyrimidine 10a as having broad spectrum antibacterial activity (MIC 0.49-3.9 μg mL-1), and reasonable antifungal activity (MIC 31.25 μg mL-1). An expeditious synthesis of 10a was optimized by varying solvents, catalysts and the use of microwave irradiation with the best conditions using DMF as a solvent, I2 (10 mol%) and a 30 minutes reaction time compared to 15 h for classic conventional heating. The pharmacokinetic properties and calculation of drug likeness of 10a suggested good traditional drug-like properties and led to the synthesis of a small library with seven compounds 10a and 10d-i showing broad antimicrobial activity (MIC = 0.49-7.81 μg mL-1) and selectivity indices of more than 5.6 against the normal colon cell line (CCD-33Co). The antifungal activity of compounds 10d-i was moderate to strong with MIC values of 1.95-15.63 μg mL-1.
- Fares, Mohamed,Abd El Hadi, Soha R.,Eladwy, Radwa A.,Shoun, Aly A.,Abdel-Aziz, Marwa M.,Eldehna, Wagdy M.,Abdel-Aziz, Hatem A.,Keller, Paul A.
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supporting information
p. 3389 - 3395
(2018/05/23)
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- Cascade Reaction by Chemo- and Biocatalytic Approaches to Obtain Chiral Hydroxy Ketones and anti 1,3-Diols
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A chemo- and biocatalytic cascade approach was applied for the stereoselective synthesis of hydroxy ketones and the corresponding 1,3-diols. A new class of tridentate N,N,O ligands was used with copper(II) complexes for the asymmetric β-borylation of α,β-unsaturated compounds. The complex containing ligand L5 emerged as the best performer, and it gave the organoborane derivatives with good ee values. The corresponding keto–alcohol compounds were then bioreduced by yeasts. The biotransformation set up with Rhodotorula rubra allowed (R)-keto–alcohols and (S,S)-diols to be obtained with up to 99 % ee and up to 99 % de in favor of the anti enantiomers.
- Gandolfi, Raffaella,Facchetti, Giorgio,Christodoulou, Michael S.,Fusè, Marco,Meneghetti, Fiorella,Rimoldi, Isabella
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p. 393 - 400
(2018/06/04)
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- Catalytic Synthesis of Chalcones and Pyrazolines Using Nanorod Vanadatesulfuric Acid: An Efficient and Reusable Catalyst
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Nanorod vanadatesulfuric acid (VSA NRs), as a recyclable and ecologically benign catalyst, was used for the one-pot synthesis of chalcones and 1,3,5-triaryl-2-pyrazolines (TAPs). Chalcones were prepared via the condensation of substituted acetophenones with aryl-aldehydes under solvent-free conditions. Subsequently, the synthesized chalcones were used for the catalytic synthesis of TAPs via two-component condensation with phenyl hydrazine in refluxing ethanol. VSA is easily prepared by a simple reaction of chlorosulfonic acid and sodium metavanadate of high purity. Compared to conventional procedures, the present protocol offers several advantages such as simplicity of the procedure, appropriate reaction times, high to excellent yields, easily work-up, recoverability, and reusability of the catalyst, and simple purification of the products.
- Nasr-Esfahani, Masoud,Daghaghale, Mona,Taei, Mahbube
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- Generation and Application of Homoenolate Equivalents Utilizing [1,2]-Phospha-Brook Rearrangement under Br?nsted Base Catalysis
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A new method for catalytic generation of a homoenolate equivalent and its application to carbon?carbon bond formation was developed by utilizing the [1,2]-phospha-Brook rearrangement under Br?nsted base catalysis. The α-oxygenated allyl anions, which can
- Kondoh, Azusa,Aoki, Takuma,Terada, Masahiro
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supporting information
p. 2769 - 2773
(2017/03/08)
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- 13C NMR spectroscopy of heterocycles: 1-phenyl-3-aryl/t-butyl-5-arylpyrazoles
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A series of chalcones 1-12 were converted to pyrazolines (1Pi-12Pi) by reaction with phenylhydrazine followed by DDQ oxidation to produce the corresponding pyrazoles (1Pz-12Pz). Three 1-phenyl-3-t-butyl-5-arylpyrazoles (13Pz-15Pz) were synthesized using an analogous approach. Molecular modeling studies predicted the 5-aryl group of the pyrazoles for both series to have a torsion angle of 52°-54° whereas the 1-phenyl group was predicted to have 35°-37° torsion angles. The 3-aryl group was predicted to be essentially coplanar (-3°) with the pyrazole system in the first series. 13C NMR data for both series, 1Pz-12Pz and 13Pz-15Pz, were collected in DMSO-d6 at 50°C. A plot of the C4 chemical shifts for 1Pz-12Pz versus Hammet constants for 5-aryl substituents yielded a very good linear correlation (R2=0.96) with a slope of 1.5. The chemical shift data for C4 showed little or no dependence on 3-aryl substituents. The result for 13Pz-15Pz, despite only three points, was consistent with the first series results and yielded a ρ value of 2.0. Distal transmission of substituent effects (5-aryl groups) to C4 of the pyrazole system was reduced by roughly 50-60% of that of the analogous planar isoxazole system, but are not consistent with results for the similarly twisted 4-bromoisoxazoles.
- Hockstedler, Amy N.,Edjah, Beatrice A.,Azhar, Saajid Z.,Mendoza, Hadrian,Brown, Nicole A.,Arrowood, Hayley B.,Clay, Andrew C.,Shah, Anand B.,Duffek, Glenda M.,Cui, Jianmei,Baumstark, Alfons L.
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p. 125 - 131
(2017/04/14)
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- A regioselective and convenient one-pot multicomponent synthesis of 9-amino-3,5-diaryl-4,9-dihydro-5H-[1,2,4]triazolo[5,1-c][1,2,4]triazepine-8-thiol
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An efficient and environment-friendly procedure for the synthesis of a new series of nitrogen bridge-head [1,2,4]triazolo[5,1-c][1,2,4]triazepine derivatives through one-pot three-component reaction of polyfunctional triazole with aromatic aldehydes and acetophenone derivatives using alcoholic sodium hydroxide solution. The same new products were prepared in classical route through reaction of triazole with the corresponding chalcones under the same conditions.
- Moustafa, Amr Hassan,Amer, Amer Anwar
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p. 1102 - 1109
(2017/05/25)
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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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- 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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- 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
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- Substituent-Controlled Chemoselective Cleavage of C = C or Csp2 - C(CO) Bond in α,β-Unsaturated Carbonyl Compounds with H-Phosphonates Leading to β-Ketophosphonates
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An unprecedented substituent-controlled chemoselective cleavage of C = C double bond or C(sp2)-C(CO) bond along with aerobic phosphorylation of α,β-unsaturated carbonyl compounds with H-phosphonates through a radical process has been disclosed. The current strategy provides an access to β-ketophosphonates under mild conditions with a wide substrate scope.
- Zhou, Yao,Rao, Changqing,Mai, Shaoyu,Song, Qiuling
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p. 2027 - 2034
(2016/03/15)
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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 and cytotoxic activities of some pyrazoline derivatives bearing phenyl pyridazine core as new apoptosis inducers
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The cyclization of chalcones 3a-3u with 3-hydrazinyl-6-phenylpyridazine 7 under basic condition led to the formation of new pyrazoline derivatives 8a-8u. All final compounds were characterized by spectral and elemental analyses. They were screened for their antiproliferative activities against A549 (lung), HepG-2 (liver), CaCo-2 (intestinal) and MCF-7 (breast) cancer cell lines. Some of the synthesized compounds exhibited promising antiproliferative activities especially compound 8k with IC50values of 8.33, 1.67 and 10?μM against HepG-2, MCF-7 and CaCo-2 cancer cell lines, respectively. Moreover, their antiproliferative activity was due to apoptosis rather than necrosis induction except compound 8h which exhibited equal apoptotic and necrotic properties. Compound 8k showed 5 fold increase in caspase-3 activity indicating that the apoptosis proceeds via caspase-3 activation.
- George, Riham F.,Fouad, Marwa A.,Gomaa, Iman E.O.
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- Novel benzothiazole based sulfonylureas/sulfonylthioureas: Design, synthesis and evaluation of their antidiabetic potential
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In the present study, twenty-eight benzothiazole based sulfonylureas/sulfonylthioureas were synthesized and were assessed for their antidiabetic effect in a normoglycemic rat model by the in vivo oral glucose tolerance test (OGTT). All the synthesized com
- Kharbanda, Chetna,Alam, Mohammad Sarwar,Hamid, Hinna,Javed, Kalim,Bano, Sameena,Ali, Yakub,Dhulap, Abhijeet,Alam, Parwez,Pasha
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p. 6777 - 6786
(2016/08/10)
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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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- Monoamine Oxidase Inhibitory Activity: Methyl- versus Chlorochalcone Derivatives
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Numerous studies have shown that chalcones are promising scaffolds for the development of new monoamine oxidase-B (MAO-B) inhibitors. As a continuation of our ongoing research into the development of reversible human MAO-B (hMAO-B) inhibitors, two series
- Mathew, Bijo,U?ar, Gülberk,Mathew, Githa Elizabeth,Mathew, Sincy,Kalatharakkal Purapurath, Praseedha,Moolayil, Fasil,Mohan, Smrithy,Varghese Gupta, Sheeba
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p. 2649 - 2655
(2016/12/23)
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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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- 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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- Method for preparing alpha and beta-unsaturated ketone
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The invention provides a method for preparing alpha and beta-unsaturated ketone. The method includes that L-proline is used as a catalyst, secondary amine is used as a cocatalyst, and the alpha and beta-unsaturated ketone can be directly synthesized in alcohol or ketone solution by means of aldol condensation under neutral conditions at one step. Compared with the traditional method, the method has the advantages that raw materials are easily available, the method is low in cost and is environmental friendly, reaction conditions are mild, solvents are clean and environmental friendly, equipment can be protected against corrosion under the neutral conditions, the catalyst is high in acid resistance, and the method is applicable to industrial production.
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Paragraph 0012; 0013; 0034; 0035; 0036; 0040; 0041
(2016/10/31)
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- A Facile FeCl3/I2-Catalyzed Aerobic Oxidative Coupling Reaction: Synthesis of Tetrasubstituted Imidazoles from Amidines and Chalcones
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A facile and efficient route for the synthesis of tetrasubstituted imidazoles from amidines and chalcones via FeCl3/I2-catalyzed aerobic oxidative coupling has been developed. This new strategy is featured by high regioselectivity an
- Zhu, Yuelu,Li, Cheng,Zhang, Jidong,She, Mengyao,Sun, Wei,Wan, Kerou,Wang, Yaqi,Yin, Bin,Liu, Ping,Li, Jianli
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supporting information
p. 3872 - 3875
(2015/08/18)
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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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- 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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- Synthesis and screening of antimicrobial activity of novel 2,5-dimethylpyrrolyl-pyrazole derivatives
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A new series of 2,5-dimethylpyrrolyl-pyrazole derivatives (5a-g) was synthesized by refluxing a mixture of substituted chalcones in ethanol with 4-(2,5-dimethylpyrrol- 1-yl) benzoic acid hydrazide. Purity of newly synthesized compounds was confirmed by TLC and melting point. The structures of all newly synthesized compounds were confirmed by spectral study such as FTIR, 1H NMR and Mass spectroscopy. The compounds were screened for their antimicrobial and antitubercular activities using broth microdilution and MABA methods respectively.
- Hallikeri,Joshi, Shrinivas D.,Kulkarni
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p. 157 - 160
(2019/01/16)
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- Graphene based material as a base catalyst for solvent free Aldol condensation and Knoevenagel reaction at room temperature
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Graphene oxide (GO) acts as a highly active heterogeneous base catalyst for a wide variety of reactions. Here we have described the catalytic activities of GO in the condensation reaction of various substituted benzaldehydes with acetophenone (aldol condensation) and with active methylene compound malononitrile (Knoevenagel reaction) at room temperature under solvent free condition. GO is characterized by powder X-ray diffraction (XRD), UV-visible spectra, Fourier transform infrared spectroscopy (FT-IR) and AFM. The experimental results showed that the GO had higher catalytic activity and it can be recycled without significant loss of its activity.
- Islam, Sk Manirul,Roy, Anupam Singha,Dey, Ram Chandra,Paul, Sumantra
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- An efficient synthesis of highly substituted indanones and chalcones promoted by superacid
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A superacid promoted one-pot process for the efficient synthesis of indanones is presented. This process enabled the formation of a dual C-C bond between aryl isopropyl ketones and benzaldehydes. Interestingly, when the reaction was performed between acetophenones and benzaldehydes, it was impeded just after the aldol condensation and resulted in the corresponding chalcones. This journal is the Partner Organisations 2014.
- Das, Amrita,Krishna Reddy, Alavala Gopi,Krishna, Jonnada,Satyanarayana, Gedu
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p. 26662 - 26666
(2014/07/21)
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- DNA interaction and cytotoxic activities of square planar platinum(II) complexes with N, S-donor ligands
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The platinum(II) complexes with N, S-donor ligands have been synthesized and characterized by physicochemical methods viz. elemental, electronic, FT-IR, 1H NMR and LC-MS spectra. The binding mode and potency of the complexes with HS DNA (Herrin
- Patel, Mohan N.,Patel, Chintan R.,Joshi, Hardik N.,Thakor, Khyati P.
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supporting information
p. 261 - 267
(2014/04/03)
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- A facile synthesis of isoindoline and Δ1-pyrrolines from chalcone and glycine by a cascade of process involving addition, in situ decarboxylation, and cyclization
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In this Letter, we report a rapid one-step entry into isoindoline and Δ1-pyrrolines from chalcone. The key step in the synthesis is the addition of glycine to chalcone. In acidic medium the reaction presumably goes through aza-Michael addition,
- Elamparuthi, Elangovan,Sarathkumar, Subramaniayan,Girija, Swaminathan,Anbazhagan, Veerappan
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supporting information
p. 3992 - 3995
(2014/07/08)
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- Synthesis, characterization of 4,6-disubstituted aminopyrimidines and their sulphonamide derivatives as anti-Amoebic agents
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The present study describes the synthesis and anti-Amoebic activity of 4,6-disubstituted aminopyrimidines (1b-10b) and their sulphonamide derivatives (1-20). All the desired compounds were characterized by spectral data and their purity was confirmed by e
- Siddiqui, Shadab Miyan,Azam, Amir
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p. 2976 - 2984
(2014/05/06)
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- Synthesis and evaluation of pyrazolines bearing benzothiazole as anti-inflammatory agents
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The present study aims at the synthesis of pyrazolines bearing benzothiazole and their evaluation as anti-inflammatory agents. The synthesized compounds were evaluated for their anti-inflammatory potential using carrageenan induced paw edema model. Two co
- Kharbanda, Chetna,Alam, Mohammad Sarwar,Hamid, Hinna,Javed, Kalim,Bano, Sameena,Dhulap, Abhijeet,Ali, Yakub,Nazreen, Syed,Haider, Saqlain
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p. 5804 - 5812
(2015/02/02)
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- Functionalization of the Benzylic C-H Bonds in Azaarenes by Cobalt-Catalyzed 1,4-Addition to Enones
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Functionalization of the C(sp3)-H bonds in azaarenes was catalyzed by CoCl2 as an inexpensive Lewis acid catalyst. Enones were demonstrated to be good C=C electrophilic acceptors for the construction of various azaarene-containing 1,4-addition products in yields of up to 95 %. Functionalization of the C(sp3)-H bonds in azaarenes catalyzed by CoCl2 as an inexpensive Lewis acid catalyst is reported. Enones are demonstrated to be good C=C electrophilic acceptors for the construction of various azaarene-containing 1,4-addition products in yields up to 95 %.
- Jamal, Zaini,Teo, Yong-Chua,Wong, Ling-Keong
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supporting information
p. 7343 - 7346
(2016/02/20)
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- Oxygen as single oxidant for two steps: Base-free one-pot Pd(ii)-catalyzed alcohol oxidation & arylation to halogen-intact β-aryl α,β-enones
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Using oxygen as the sole oxidant for two steps, we developed a new method to synthesize β-aryl α,β-enones by fine-tuning the Pd(ii)-catalyzed oxidation of allyl alcohol to subsequent arylation with arylboronic acids, arylboronic ester and aryltrifluoroborate salt. This one-pot green method does not require copper salt, base, and intermediate isolation. Halogen-bearing chalcones, dibenzylideneacetones and arylalkyl enones were synthesized in good yields. This journal is
- Vellakkaran, Mari,Andappan, Murugaiah M. S.,Nagaiah, Kommu
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p. 45490 - 45494
(2014/12/10)
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- Microwave-assisted synthesis and tyrosinase inhibitory activity of chalcone derivatives
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A series of chalcones and their derivatives were synthesized, and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant inhibitory activity, and four compounds exhibited more potent tyrosinase inhibitory activity than the reference standard inhibitor kojic acid (5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one). Specifically, 1-(-1-(4-methoxyphen- yl)-3-phenylallylidene)thiosemicarbazide (18) exhibited the most potent tyrosinase inhibitory activity with IC50 value of 0.274 μm. The inhibition mechanism analysis of 1-(-1-(2,4-dihydroxyphenyl)-3-phenylallylidene) thiosemicarbazide (16) and 1-(-1-(4-methoxyphenyl)-3-phenylallylidene) thiosemicarbazide (18) demonstrated that the inhibitory effects of the two compounds on the tyrosinase were irreversible. Preliminary structure activity relationships' analysis suggested that further development of such compounds might be of interest.
- Liu, Jinbing,Chen, Changhong,Wu, Fengyan,Zhao, Liangzhong
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- Biomimetic hydrogenation: A reusable NADH co-enzyme model for hydrogenation of α,β-epoxy ketones and 1,2-diketones
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A biomimetic method has been developed to transform α,β-epoxy ketones or 1,2-diketones into corresponding β-hydroxy ketones or α-hydroxy ketones using a catalytic amount of BNAH or BNA +Br-. The regeneration of BNAH or BNA+Br - is achieved by a mixture of HCOOH/Et3N. A radical mechanism is proposed to explain these observations.
- Huang, Qiang,Wu, Ji-Wei,Xu, Hua-Jian
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supporting information
p. 3877 - 3881
(2013/07/05)
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- Chemoselective transfer hydrogenation of α,β-unsaturated ketones catalyzed by pincer-Pd complexes using alcohol as a hydrogen source
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A pincer-Pd complex was utilized in the chemoselective transfer hydrogenation of α,β-unsaturated ketones using n-BuOH as a hydrogen source and solvent. Good to excellent yields were obtained for various substrates even with reducible groups. Based on deuterium-labeling experiments, the reaction mechanism is proposed to occur via a pincer-Pd-hydride intermediate.
- Ding, Boqiang,Zhang, Zhenfeng,Liu, Yangang,Sugiya, Masashi,Imamoto, Tsuneo,Zhang, Wanbin
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supporting information
p. 3690 - 3693
(2013/08/23)
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- PAA-supported Hantzsch 1,4-dihydropyridine ester: An efficient catalyst for the hydrogenation of α,β-epoxy ketones
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A new type of water-soluble polymer-supported NADH co-enzyme model-PAA (polyacrylic acid)-supported Hantzsch 1,4-dihydropyridine ester (PAA-HEH) was designed and synthesized. Catalytic amount of the supported reagent was used in the hydrogenation of α,β-epoxy ketones to the corresponding β-hydroxy ketones and showed great catalytic efficiency in the reduction reaction. This PAA-HEH was an optimal potential for recycling use.
- Zhou, Xin-Feng,Wang, Peng-Fei,Geng, Ye,Xu, Hua-Jian
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supporting information
p. 5374 - 5377
(2013/09/12)
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