cas 19672-59-4, 4,4'-Dichlorochalcone | Articles data

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Solution phase combinatorial synthesis and screening of mini libraries of arylchalcones for antibacterial activity
The solution-phase combinatorial synthesis of aryl chalcones was studied by synthesizing a 6x4 array mini library. The mini libraries of chalcones were synthesized by condensation of 4-substituted acetophenones and various aryl/heteroaryl carbaldehydes. A
Bhatia, Neela M.,Mahadik, Kakasaheb
p. 259 - 267
(2008)
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Synthesis of tert -Butyl 1,3-Diaryl-3-oxopropylcarbamates by a regiocontrolled reduction of ketoaziridines
A new, convenient approach for the reductive ring opening of N-H ketoaziridines is described. Treatment of N-H ketoaziridines with di-tert-butyl dicarbonate [(Boc)2O] in the presence of sodium iodide and nickel(II) chloride results in the corresponding tert-butyl 1,3-diaryl-3-oxopropylcarbamates by a regiocontrolled reaction. The structure of the regioisomeric product was confirmed by X-ray crystal structure analysis.
Samimi, Heshmat A.,Yamin, Bohari M.,Saberi, Fatemeh
p. 129 - 133
(2015)
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Stereo-controlled deamination of ketoaziridines using Ph3P, I2
Ph3P, I2is an efficient reagent for the stereo-controlled deamination of non-activated aziridines, N-H and N-alkyl aziridines, using. The method works gives the corresponding trans-alkenes from both cis and trans-aziridines. A plausible mechanism is proposed for the ring opening and deamination of keto-aziridines in the presence of Ph3P, I2.
Samimi, Heshmat Allah,Kiyani, Hamzeh,Shams, Zahra
p. 282 - 284
(2013)
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Synthesis of lithium/cesium-Zagronas from zagrosian natural asphalt and study of their activity as novel, green, heterogeneous and homogeneous nanocatalysts in the Claisen–Schmidt and Knoevenagel condensations
A novel, heterogeneous and homogeneous basic nanocatalysts were synthesized by grafting of lithium and cesium on zagrosian natural asphalt sulfonate (Li/Cs-Zagronas). The activity of these catalysts was examined in the Claisen–Schmidt and Knoevenagel condensations under mild reaction conditions. Li/Cs-Zagronas were characterized by FT-IR spectroscopy, scanning electron microscopy, X-ray diffraction, energy-dispersive spectroscopy, inductively coupled plasma and thermogravimetric analysis techniques. These nanocatalysts were removed by simple filtration and reused several times without any deterioration of activity.
Soleiman-Beigi, Mohammad,Ghalavand, Saba,Venovel, Hadis Gholami,Kohzadi, Homa
p. 3267 - 3279
(2021/06/17)

Synthesis of chalcone derivatives by phthalhydrazide-functionalized tio2-coated nano-fe3o4 as a new heterogeneous catalyst
Phthalhydrazide immobilized on TiO2-coated nano Fe3O4 (Fe3O4-P) was synthesized and characterized by FT-IR, XRD, SEM, EDS and VSM analysis. The resulting magnetic nanocatalyst was used as a catalyst for the synthesis of chalcone derivatives which affords the desired products in good to excellent yields. This catalyst can be isolated readily after completion of the reaction by an external magnetite field and reused several times without significant loss of activity.
Farahi, Mahnaz,Karami, Bahador,Keshavarz, Raziyeh,Nia, Forough Motamedi
p. 407 - 414
(2021/09/07)

Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water
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
supporting information

(2021/02/27)

New nicotinic acid-based 3,5-diphenylpyrazoles: design, synthesis and antihyperlipidemic activity with potential NPC1L1 inhibitory activity
Nicotinic acid hydrazide was incorporated into new 4,5-dihydro-5-hydroxy-3,5-diphenylpyrazol-1-yl derivatives. Compounds 6a–h were synthesized, and their antihyperlipidemic activity was evaluated in high cholesterol diet-fed rat model. Compounds 6e, 6f were found to decrease the levels of serum total cholesterol by 14–19% compared to control group. Total triglycerides were also reduced by 24–28% and LDL cholesterol by 16%. As expected from parent niacin, compounds 6e and 6f caused an elevation of HDL cholesterol by 33–41%. Docking study supported the ability of designed compounds to block NPC1L1 active site in a manner similar to that observed with ezetimibe.
Shoman, Mai E.,Aboelez, Moustafa O.,Shaykhon, Montaser Sh. A.,Ahmed, Sanaa A.,Abuo-Rahma, Gamal El-Din A.,Elhady, Omar M.
p. 673 - 686
(2020/02/25)

Palladium-Catalyzed Allyl-Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H2as Sole Reductant
Catalytic carbon-carbon bond formation building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H2 as the sole reductant for the palladium-catalyzed allyl-allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols as well as allylic ethers proceed smoothly to deliver the C-C coupling products under 1 atm of H2. Kinetic studies suggested that the dinuclear palladium species was involved in the catalytic cycle.
Zhou, Xibing,Zhang, Guoying,Huang, Renbin,Huang, Hanmin
supporting information
p. 365 - 369
(2021/01/26)

Boosting the catalytic performance of zinc linked amino acid complex as an eco-friendly for synthesis of novel pyrimidines in aqueous medium
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
(2021/02/26)

Bu4NHSO4-Catalyzed Direct N-Allylation of Pyrazole and its Derivatives with Allylic Alcohols in Water: A Metal-Free, Recyclable and Sustainable System
Allylic amines are valuable and functional building blocks. Direct N-allylation of pyrazole and its derivatives as an atom economic strategy to provide allylic amines has been achieved only using commercial Bu4NHSO4 as the metal-free catalyst and water as the solvent without any additives. 11–93% isolated yields were obtained for the N-allylation of pyrazole and its derivatives with allylic alcohols. Bu4NHSO4 could be reused for six times by simple extraction nearly without loss of catalytic activity and was also suitable for a gram-scale production. The reaction of allylic ether and pyrazole did not occur to give the desired product indicated that allylic ether was not the active intermediate in the pathway. Density functional theory (DFT) calculations reveal that there are hydrogen bonding effects among substrates, solvent and catalyst, especially the one formed between allylic alcohol and H2O. Control experiments in different protic solvents further demonstrate the intermolecular hydrogen bonding of allylic alcohol and water. (Figure presented.).
Zhuang, Hongfeng,Lu, Nan,Ji, Na,Han, Feng,Miao, Chengxia
supporting information
p. 5461 - 5472
(2021/09/29)

Novel potent and selective DPP-4 inhibitors: Design, synthesis and molecular docking study of dihydropyrimidine phthalimide hybrids
Background: Dipeptidyl peptidase-4 (DPP-4) inhibitors have emerged as antihyperglycemic agents that improve glycemic control in type 2 diabetic patients, either as monotherapy or in combination with other antidiabetic drugs. Methods: A novel series of dihydropyrimidine phthalimide hybrids was synthesized and evaluated for their in vitro and in vivo DPP-4 inhibition activity and selectivity using alogliptin as reference. Oral glucose tolerance test was assessed in type 2 diabetic rats after chronic treatment with the synthesized hybrids ± metformin. Cytotoxicity and antioxidant assays were performed. Additionally, molecular docking study with DPP-4 and structure activity relationship of the novel hybrids were also studied. Results: Among the synthesized hybrids, 10g, 10i, 10e, 10d and 10b had stronger in vitro DPP-4 inhibitory activity than alogliptin. Moreover, an in vivo DPP-4 inhibition assay revealed that 10g and 10i have the strongest and the most extended blood DPP-4 inhibitory activity compared to alogliptin. In type 2 diabetic rats, hybrids 10g, 10i and 10e exhibited better glycemic control than alogliptin, an effect that further supported by metformin combination. Finally, 10j, 10e, 10h and 10d had the highest radical scavenging activity in DPPH assay. Conclusions: Hybrids 10g, 10i and 10e are potent DPP-4 inhibitors which may be beneficial for T2DM treatment.
Mourad, Ahmed A. E.,Khodir, Ahmed E.,Saber, Sameh,Mourad, Mai A. E.
p. 1 - 24
(2021/02/26)

Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process
Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.
Du, Chan,Fang, Jianghua,Fang, Yewen,Lei, Wan,Li, Yan,Liu, Yongjun
supporting information
p. 8502 - 8506
(2021/10/20)

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
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
(2020/07/06)

Aryl-4,5-dihydro-1H-pyrazole-1-carboxamide derivatives bearing a sulfonamide moiety show single-digit nanomolar-to-subnanomolar inhibition constants against the tumor-associated human carbonic anhydrases IX and XII
A series of new 3-phenyl-5-aryl-N-(4-sulfamoylphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide derivatives was designed here, synthesized, and studied for carbonic anhydrase (CAs, EC 4.2.1.1) inhibitory activity against the human (h) isozymes I, II, and VII (cytosolic, off-target isoforms), and IX and XII (anticancer drug targets). Generally, CA I was not effectively inhibited, whereas effective inhibitors were identified against both CAs II (KIs in the range of 5.2-233 nM) and VII (KIs in the range of 2.3-350 nM). Nonetheless, CAs IX and XII were the most susceptible isoforms to this class of inhibitors. In particular, compounds bearing an unsubstituted phenyl ring at the pyrazoline 3 position showed 1.3-1.5 nM KIs against CA IX. In contrast, a subset of derivatives having a 4-halo-phenyl at the same position of the aromatic scaffold even reached subnanomolar KIs against CA XII (0.62-0.99 nM). Docking studies with CA IX and XII were used to shed light on the derivative binding mode driving the preferential inhibition of the tumor-associated CAs. The identified potent and selective CA IX/XII inhibitors are of interest as leads for the development of new anticancer strategies.
Ceruso, Mariangela,Gratteri, Paola,Hargunani, Priya,Kazaks, Andris,Leitans, Janis,Nocentini, Alessio,Supuran, Claudiu T.,Tadge, Nikhil,Tars, Kaspars,Toraskar, Mrunmayee P.
(2020/04/27)

Discovery of Novel Approach for Regioselective Synthesis of Thioxotriaza-Spiro Derivatives via Oxalic Acid
A vital approach for the synthesis of a range of novel thioxotriaza-spiro derivatives is described. These new heterocyclic systems are obtained via oxalic acid catalyzed reaction of α,β-unsaturated ketones in the presence of 5,6-diamino-2-mercaptopyrimidi
Gopinatha, Vindya K.,Mantelingu, Kempegowda,Raghavan, Sathees C.,Rangappa, Kanchugarakoppal S.,Swarup, Hassan A.
supporting information
p. 2004 - 2009
(2019/10/28)

Naphtho[2,3-: B] furan-4,9-dione synthesis via palladium-catalyzed reverse hydrogenolysis
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
supporting information
p. 2348 - 2351
(2019/02/27)

Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes
Formal [5 + 1] cycloadditions between aryl-substituted vinylcyclopropanes and nitrenoid precursors are reported. The method, which employs Rh2(esp)2 as a catalyst, leads to the highly regioselective formation of substituted tetrahydropyridines. Preliminary mechanistic studies support a stepwise, polar mechanism enabled by the previously observed Lewis acidity of Rh-nitrenoids. Overall, this work expands the application of nitrene-transfer cycloaddition, a relatively underexplored approach to heterocycle synthesis, to the formation of six-membered rings.
Combee, Logan A.,Johnson, Shea L.,Laudenschlager, Julie E.,Hilinski, Michael K.
supporting information
p. 2307 - 2311
(2019/04/10)

Preparation and Application of Amino Phosphine Ligands Bearing Spiro[indane-1,2′-pyrrolidine] Backbone
P,Nsp3-bidentate chiral ligands bearing spiro[indane-1,2′-pyrrolidine] backbone were prepared in gram scale for the first time. Pd complexes of these air-stable amino phosphine ligands could catalyze asymmetric allylic substitutions of malonate-, alcohol-, and amine-type nucleophiles in up to 97percent ee and 99percent yield. A crystal structure of [Pd(II)(η3-1,3-diphenylallyl)(ligand)]PF6 indicated possible transition states of the catalytic reactions. These ligands are characteristic of a very rigid backbone, which is simple but highly effective. They rival C2-symmetric bisphosphine, P,Nsp2-bidentate, and P,Nsp3-bidentate ligands in tested allylic substitutions. ?
Feng, Lifei,Jiao, Peng,Li, Hongjie,Li, Shasha,Zhang, Jinxia
p. 9460 - 9473
(2019/08/26)

COMPOSITION FOR PROTECTING KIDNEY CONTAINING CHALCONE DERIVATIVES
The present invention relates to a composition for protecting a kidney or a composition for alleviating kidney diseases which contains a chalcone derivative. When the compound according to the present invention is used, the kidney can be protected from nephrotoxicity due to drugs and the like. Therefore, by utilizing the present specification, it is possible to make a great contribution to fields of patient treatment and welfare.COPYRIGHT KIPO 2019
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(2019/09/11)

N1-benzenesulfonyl-2-pyrazoline hybrids in neurological disorders: Syntheses, biological screening and computational studies
A novel series of 1,3,5-trisubstituted-2-pyrazolines (5a-5t) was prepared via Claisen Schmidt condensation, followed by heterocyclization with hydrazine hydrate, substitution of N1 hydrogen of 2-pyrazoline nucleus with 4-chlorobenzenesulfonylchloride, app
Tripathi, Avinash C.,Upadhyay, Savita,Paliwal, Sarvesh,Saraf, Shailendra K.
p. 126 - 148
(2018/02/14)

Derivatives of 4,5-dihydro (1H) pyrazoles as possible MAO-A inhibitors in depression and anxiety disorders: synthesis, biological evaluation and molecular modeling studies
A series of 1,3,5-trisubstituted-2-pyrazoline derivatives (3a–3t) were synthesized in appreciable yields by substituting N1 position of 2-pyrazoline nucleus with 4-nitrobenzenesulfonylchloride using conventional and microwave assisted synthetic approaches
Tripathi, Avinash C.,Upadhyay, Savita,Paliwal, Sarvesh,Saraf, Shailendra K.
p. 1485 - 1503
(2018/03/29)

An improved synthesis of pyrido[2,3-: D] pyrimidin-4(1 H)-ones and their antimicrobial activity
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.
supporting information
p. 3389 - 3395
(2018/05/23)

Direct Reduction of Allylic Alcohols Using Isopropanol as Reductant
The lithium cation-catalyzed direct reduction of allylic alcohols to alkenes using isopropanol as a hydride donor was developed. The hydride transfer of the in situ-generated lithium isopropoxide to an allylic cation is the key process in this transformation. The reaction generates only water and acetone as byproducts, which highlights the synthetic utility of this method. (Figure presented.).
Sai, Masahiro
supporting information
p. 3482 - 3487
(2018/09/14)

Microwave-irradiated synthesis and biological evaluation of 3,5-diaryl-1-phenyl-2-pyrazolines as antibacterial and anti-inflammatory agents
In a wide search program towards a biologically active antibacterial and anti-inflammatory agents, a series of 3,5-diaryl-1-phenyl-2-pyrazoline have been synthesized with excellent yields employing microwave techniques starting from substituted α,β-unsaturated carbonyl compounds which undergo cyclization reactions with phenylhydrazine. The structures of newly synthesized compounds were characterized and confirmed on the basis of FT-IR, 1H NMR and mass spectral analyses. The synthesized compounds 3,5-diaryl-1-phenyl-2-pyrazolines had shown significant activity against Staphylococcus aureus (MTCC 87), Escherichia coli (MTCC 40), Pseudomonas aeruginosa (MTCC 424) and Proteus vulgaris (MTCC 426) by cup plate method using tetracycline-SD 037 as a reference standard. The anti-inflammatory property of 1,3,5-diaryl-1-phenyl-2-pyrazolines were screened by using carragenan induced paw edema method in Wistar rat. The anti-inflammatory activities were comparable to that of the standard drug diclofenac. The safety of 3,5-diaryl-1-phenyl-2-pyrazolines were reflected by toxicity studies.
Kumar, Anjan,Rout, Sradhasini,Panda, Jnyanaranjan,Sahoo, Biswa Mohan,Banik, Bimal Krishna
p. 1321 - 1326
(2020/06/27)

Ultrasound-mediated synthesis, biological evaluation, docking and in vivo acute oral toxicity study of novel indolin-2-one coupled pyrimidine derivatives
The work reports ultrasound-mediated greener synthesis of 11 novel 3-(4-(4-chlorophenyl)-6-(substituted phenyl/heteryl)pyrimidin-2-ylimino)indolin-2-one (7a–7k) derivatives. The synthesized derivatives were evaluated for their in vitro anticancer activity against a panel of selected human cancer cell lines of breast (MCF-7), cervix (HeLa), prostate (PC-3) and lung (A-549). Among the tested compounds, 7b exhibited most promising in vitro anticancer activity against HeLa, PC-3 and A-549 with GI50 value 15.38, 19.67 and 4.37?μM, respectively. The compounds (7a–7k) were also screened for induction of apoptosis and morphological changes in cancer cells at their GI50 concentration. The treatment of HeLa, PC-3 and A549 cancer cells with 7b and treatment of MCF-7 cancer cells with 7h showed apoptosis and morphological changes such as cell shrinkage, cell wall deformation and reduced number of viable cells. The compound 7b has shown almost 5.00 times more selectivity for PC-3 cancer cell lines in comparison to the RWPE-1 normal prostate epithelial cells. Molecular docking study has been carried out, which replicates results of biological activity in cases of initial hits 7b, 7c and 7d, suggesting that these compounds have a potential to become lead molecules in the drug discovery process. In silico ADMET study was performed for predicting pharmacokinetic properties and toxicity profile of the synthesized compounds and expressed good oral drug-like behaviour. An in vivo acute oral toxicity study was performed using Swiss albino mice for the most active compounds 7b and 7c, and results indicate that the compounds are non-toxic in nature.
Nikalje, Anna Pratima G.,Tiwari, Shailee V.,Sangshetti, Jaiprakash N.,Damale, Manoj D.
p. 3031 - 3059
(2018/02/06)

A catalytic allylic cation-induced intermolecular allylation-semipinacol rearrangement
A catalytic intermolecular semipinacol rearrangement induced by allylic carbocations has been realized. This tandem reaction is highly efficient under the catalysis of ZnBr2, generating a wide range of α-homoallyl substituted ketones which contain all-carbon quaternary centres in good to excellent yields (up to 98%) with moderate to high diastereoselectivities (up to >20?:?1). Synthetic application of this novel methodology in the construction of core structures of natural products is also reported.
Xu, Ming-Hui,Dai, Kun-Long,Tu, Yong-Qiang,Zhang, Xiao-Ming,Zhang, Fu-Min,Wang, Shao-Hua
supporting information
p. 7685 - 7688
(2018/07/15)

Synthesis of stable benzimidazole derivatives bearing pyrazole as anticancer and EGFR receptor inhibitors
A new series of benzimidazole linked pyrazole derivatives were synthesized by cyclocondensation reaction through one-pot multicomponent reaction in absolute ethanol. All the synthesized compounds were tested for their in vitro anticancer activities on fiv
Akhtar, Md. Jawaid,Khan, Ahsan Ahmed,Ali, Zulphikar,Dewangan, Rikeshwer Prasad,Rafi, Md.,Hassan, Md. Quamrul,Akhtar, Md. Sayeed,Siddiqui, Anees Ahmad,Partap, Sangh,Pasha, Santosh,Yar, M. Shahar
p. 158 - 169
(2018/03/24)

Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties
The three-component reaction between alkyl- or arylamines, β-ketoesters and chalcones in refluxing ethanol containing a catalytic amount of Ce(IV) ammonium nitrate allowed the construction of a large library of highly substituted dihydro-m-terphenyl derivatives containing β-alkylamino- or β-arylamino ester moieties. This process generates three new bonds and one ring and proceeds in high atom economy, having two molecules of water as the only side product. Another domino process, in which the original MCR was telescoped with a subsequent aza Michael/retro-aza Michael sequence, allowed the one-pot preparation of a library of compounds with a N-unsubstituted β-aminoester fragment. Finally, to extend the structural diversity of these libraries, we also examined the aromatization of the central ring of our compounds in the presence of dichlorodicyanoquinone. This reaction sequence did not affect the integrity of a stereogenic center belonging to the amino component.
Rocchi, Damiano,González, Juan F.,Gómez-Carpintero, Jorge,González-Ruiz, Víctor,Martín, M. Antonia,Sridharan, Vellaisamy,Menéndez, J. Carlos
p. 722 - 731
(2018/10/20)

Synthesis of symmetrical and unsymmetrical triarylpyrylium ions: Via an inverse electron demand Diels-Alder reaction
BF3·OEt2 mediated inverse electron demand Diels-Alder (IEDDA) reaction of chalcones with aryl acetylenes is reported for the synthesis of symmetrical and unsymmetrical 2,4,6-triarylpyrylium ions. The protocol provides an effective one-pot method for the utilization of readily available simple substrates under mild reaction conditions leading to a diverse array of pyrylium ions in moderately good yield.
Fathimath Salfeena,Basavaraja,Ashitha,Kumar, V. Praveen,Varughese, Sunil,Suresh, Cherumuttathu H.,Sasidhar
supporting information
p. 12463 - 12466
(2018/11/20)

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
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
p. 1102 - 1109
(2017/05/25)

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols
Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.
Chan, Chieh-Kai,Tsai, Yu-Lin,Chang, Meng-Yang
p. 3368 - 3376
(2017/05/22)

Silver-Catalyzed Cross-Olefination of Donor and Acceptor Diazo Compounds: Use of N-Nosylhydrazones as Diazo Surrogate
The cross-olefination reaction of donor and acceptor diazo compounds was explored. The use of N-nosylhydrazones as diazo surrogates and the dependence on silver catalysis were crucial for the reaction development. A variety of (hetero)aryl N-nosylhydrazones and α-diazo esters, amides, and phosphonates were compatible, and the functionalized alkene products were afforded in good to high yields with moderate (Z)/(E) selectivities. The experimental and DFT calculation results suggest that the cross-selectivity is due to selective activation of the silver catalyst for donor diazo compounds.
Liu, Zhaohong,Liu, Binbin,Zhao, Xue-Feng,Wu, Yan-Bo,Bi, Xihe
supporting information
p. 928 - 932
(2017/02/15)

Bifunctional Thiourea-Catalyzed Stereoablative Retro-Sulfa-Michael Reaction: Concise and Diastereoselective Access to Chiral 2,4-Diarylthietanes
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
p. 429 - 439
(2016/12/24)

Facile epoxidation of α, β-unsaturated ketones with urea-2,2-dihydroperoxypropane as a new oxidant
Abstract: Various aromatic α, β-unsaturated ketones were successfully transformed into their corresponding epoxides using urea-2,2-dihydroperoxypropane as the oxygen source for the first time. The reactions were carried out under mild alkaline conditions at room temperature in high yields and short reaction times. Graphical Abstract: [Figure not available: see fulltext.]
Khosravi, Kaveh,Naserifar, Shirin
p. 323 - 328
(2017/01/10)

Metal-Free and Efficient Epoxidation of α,β-Unsaturated Ketones with 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as a Powerful Solid Oxidant
1,1,2,2-Tetrahydroperoxy-1,2-diphenylethane was used for the efficient and metal-free epoxidation of various α,β-unsaturated ketones, carried out under mild alkaline conditions at room temperature.
Khosravi, Kaveh,Naserifar, Shirin,Mahmoudi, Boshra
p. 683 - 689
(2017/06/19)

Synthesis, molecular docking study, and cytotoxic activity of 1,3,5-triaryl pyrazole derivatives
Synthesis, molecular docking study, and cytotoxic activity of a new group of 1,3,5-triaryl pyrazole derivatives were be studied. The antiproliferative activity of the final compounds were examined in MCF-7, AGS, HT-29 and NIH3T3 cell lines by MTT assay, u
Ghasemi, Maryam,Ghadbeighi, Sajad,Amirhamzeh, Amirali,Tabatabai, Seyed Abbas,Ostad, Seyed Nasser,Shafiee, Abbas,Amini, Mohsen
p. 121 - 128
(2016/03/12)

An expeditious one-pot microwave facilitated versus conventional syntheses: In vivo biological screening and molecular docking studies of some 3,5-disubstituted-4,5-dihydro-(1H)-pyrazole derivatives
A series of 3,5-disubstituted-2-pyrazoline derivatives (2a-2t) were synthesized by reacting different aromatic/heteroaromatic aldehydes and ketones, in a two-step reaction through Claisen Schmidt condensation, followed by cyclization of the resulted chalc
Tripathi, Avinash C.,Upadhyay, Savita,Paliwal, Sarvesh,Saraf, Shailendra K.
p. 390 - 406
(2016/02/19)

Iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate: Synthesis of 3,5-disubstituted 1H-pyrazoles
We have developed an iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate. Various 3,5-disubstituted 1H-pyrazoles were obtained in good to excellent yields. This method offers several advantages, including room-temperature conditions, short reaction time, high yields, simple work-up procedure, and use of air as an oxidant. The catalyst can be recovered and reused five times without loss of activity.
Zhao, Junlong,Qiu, Jun,Gou, Xiaofeng,Hua, Chengwen,Chen, Bang
p. 571 - 578
(2016/04/20)

Synthesis and cytotoxic activities of some pyrazoline derivatives bearing phenyl pyridazine core as new apoptosis inducers
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.
p. 48 - 59
(2016/08/08)

Novel benzothiazole based sulfonylureas/sulfonylthioureas: Design, synthesis and evaluation of their antidiabetic potential
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
p. 6777 - 6786
(2016/08/10)

Monoamine Oxidase Inhibitory Activity: Methyl- versus Chlorochalcone Derivatives
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
p. 2649 - 2655
(2016/12/23)

Monitoring the DNA by ruthenium complexes of heterocyclic N,S-donor ligands and evaluation of biological activities
Neutral N,S-donor bidentate ligands have been synthesized and characterized by NMR and IR spectroscopic techniques. The ligands have been used to synthesized ruthenium(II) complexes ([Ru(L1–L6)PPh3)2Cl2/su
Karia, Parag S.,Vekariya, Pankajkumar A.,Patidar, Anshul P.,Patel, Ravi R.,Patel, Mohan N.
p. 1903 - 1914
(2016/10/21)

Direct Regioselective [3 + 2]-Cyclization Reactions of Ambivalent Electrophilic/Nucleophilic β-Chlorovinyl Dithianes: Access to Cyclopentene Derivatives
The highly regioselective and operationally straightforward [3 + 2] cyclizations of β-chlorovinyl dithianes with α,β-unsaturated carbonyl compounds have been developed. This protocol provides direct access to highly functionalized cyclopentenes with perfect chemo- and regioselectivities under extremely mild reaction conditions. In particular, the unprecedented cyclization allows for the selective preparation of hydroxylated cyclopentenes.
Liang, Yongping,Lai, Junshan,Liu, Teng,Tang, Shouchu
supporting information
p. 5086 - 5089
(2016/10/14)

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
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
p. 661 - 671
(2017/01/13)

Metal-free allylation of electron-rich heteroaryl boronic acids with allylic alcohols
A convenient and regioselective cross-coupling of heteroaryl boronic acids with allylic alcohols under catalyst-free reaction conditions is described. The developed procedure is simple, works under external oxidant- and metal-free conditions, and proves to be very general with an unprecedented ortho-selectivity. This approach represents one of the very few examples of ortho-functionalization of boronic acids.
Li, Xue-Dong,Xie, Li-Jun,Kong, De-Long,Liu, Li,Cheng, Liang
p. 1873 - 1880
(2017/03/10)

Transition-Metal-Free Synthesis of Homo- and Hetero-1,2,4-Triaryl Benzenes by an Unexpected Base-Promoted Dearylative Pathway
An unprecedented approach for the synthesis of homo- and hetero-1,2,4-triaryl benzenes has been developed using a simple base-mediated reaction of either α-aryl cinnamyl alcohols or α,γ-di-aryl propanones. The salient feature of this strategy involves the sequential hydride transfer, regiospecific condensation, regiospecific dearylation, and aromatization under metal-free reaction conditions. The synthesis of unsymmetrically substituted triphenylenes by oxidative coupling of the synthesized 1,2,4-triaryl benzenes has also been demonstrated.
Rehan, Mohammad,Maity, Sanjay,Morya, Lalit Kumar,Pal, Kaushik,Ghorai, Prasanta
supporting information
p. 7728 - 7732
(2016/07/07)

Method for preparing chalcone compound
The invention relates to a method for preparing a chalcone compound. The method utilizes organic solutions of acetophenone or its derivative and benzyl alcohol or its derivative as reaction substrates and a metallic oxide as a catalyst to prepare the chalcone compound through oxidative condensation. The method comprises mixing acetophenone or its derivative, benzyl alcohol or its derivative and the metallic oxide in an organic solvent, putting the mixture into a pressure container, sealing the pressure container, stirring the mixture at a temperature of 40-150 DEG C for 0.5-24h and separating the reaction product to obtain the chalcone compound. The method has the advantages of easy separation of the product from the catalyst, catalyst recycle, simple reaction process and operation easiness and has a chalcone yield of 66%.
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Paragraph 0082-0083

(2017/02/28)

Transition-Metal-Free N-Arylation of Pyrazoles with Diaryliodonium Salts
A new synthetic method was developed for the N-arylation of pyrazoles using diaryliodonium salts. The transformation does not require any transition-metal catalyst and provides the desired N-arylpyrazoles rapidly under mild reaction condition in the presence of aqueous ammonia solution as a mild base without the use of inert atmosphere. The chemoselectivity of unsymmetric diaryliodonium salts was also explored with large number of examples.
Gonda, Zsombor,Novák, Zoltán
supporting information
p. 16801 - 16806
(2015/11/16)

Discovery and Pharmacophore Studies of Novel Pyrazole-Based Anti-Melanoma Agents
Due to the rising incidence and lack of effective treatments, malignant melanoma is the most dangerous form of skin cancer, so that new treatment strategies are urgently needed. Several recent developments indicate that the V600E mutant BRAF (BRAFV60
Li, Qing-Shan,Lü, Xian-Hai,Yang, Yang,Ruan, Ban-Feng,Yao, Ri-Sheng,Liao, Chen-Zhong
p. 116 - 132
(2015/10/19)

Mild and efficient reductive deoxygenation of epoxides to olefins with tin(II) chloride/sodium iodide as a novel reagent
A highly efficient and green protocol is reported for the reductive deoxygenation of organic epoxides to olefins using tin(II) chloride/sodium iodide as a novel reagent. The reaction gives an excellent yield (85-96%) in ethanol under reflux within 2-10 minutes, without affecting other functional groups. The advantages of our method are the use of inexpensive reagents, the eco-friendly and green reaction conditions, and the short reaction times and high yields.
Pathe, Gulab Khushalrao,Ahmed, Naseem
supporting information
p. 3542 - 3552
(2015/11/17)

An efficient synthesis of highly substituted indanones and chalcones promoted by superacid
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
p. 26662 - 26666
(2014/07/21)

An efficient simple one-pot synthesis, characterization and structural studies of some 1,2,3,5-tetraarylpentane-1,5-diones
A series of 1,2,3,5-tetraarylpentane-1,5-diones (9-23) were synthesised by simple one-pot method and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral techniques. The structure of 3-(4-fluorophenyl)-1,2,5-triphenylpentane-1,5-dione (10) was determined by single crystal X-ray diffraction analysis. The compound 10 crystallize in monoclinic crystal system, in C2/c space group. The torsional angle between the two keto groups was found to be -29.50. The C(23)C(22)C(15)C(8)C(7) chain is almost planar with "W" conformation and observed maximum deviation is 0.122 ? for C(15) from the C(23)/C(22)/C(15)/C(8)/C(7) plane.
Senthilkumar,Neelakandan,Manikandan
p. 1 - 8
(2013/12/04)