- Bu4NHSO4-Catalyzed Direct N-Allylation of Pyrazole and its Derivatives with Allylic Alcohols in Water: A Metal-Free, Recyclable and Sustainable System
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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
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supporting information
p. 5461 - 5472
(2021/09/29)
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- Design and synthesis of quinoline-pyrimidine inspired hybrids as potential plasmodial inhibitors
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Presently, artemisinin-based combination therapy (ACT) is the first-line therapy of Plasmodium falciparum malaria. With the emergence of malaria parasites that are resistant to ACT, alternative antimalarial therapies are urgently needed. In line with this
- Kayamba, Francis,Malimabe, Teboho,Ademola, Idowu Kehinde,Pooe, Ofentse Jacob,Kushwaha, Narva Deshwar,Mahlalela, Mavela,van Zyl, Robyn L.,Gordon, Michelle,Mudau, Pertunia T.,Zininga, Tawanda,Shonhai, Addmore,Nyamori, Vincent O.,Karpoormath, Rajshekhar
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- Heteroleptic copper(I) complexes as energy transfer photocatalysts for the intermolecular [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides
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The [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides can be effectively catalyzed by heteroleptic copper(I) complexes. The reactions were carried out under mild reaction conditions and the products were obtained in 20–72% yield under visible light irradiation. The copper-based photocatalyst comprised of the rigid phenanthroline ligand with substituents at the 2,9-positions and the 4,7-positions showed high activity in the photodimerization via an energy transfer pathway.
- Wu, Qing-An,Ren, Chen-Chao,Chen, Feng,Wang, Tian-Qi,Zhang, Yu,Liu, Xue-Fen,Chen, Jian-Bin,Luo, Shu-Ping
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supporting information
(2021/05/10)
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- Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine
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A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.
- Banerjee, Prabal,Kumar, Pankaj,Kumar, Rakesh
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supporting information
p. 6535 - 6550
(2020/06/09)
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- N-Heterocyclic Carbene Catalyzed Synthesis of Trisubstituted Epoxides via Tandem Amidation/Epoxidation Sequence
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A tandem amidation/epoxidation sequence between various substituted chalcones and N,N-dimethylformamide (DMF) for the synthesis of trisubstituted epoxides employing N-heterocyclic carbene catalysis was developed. This reaction was performed under metal-free conditions in the presence of tert-butyl hydroperoxide (TBHP) as the oxidant. Trisubstituted epoxides bearing a ketone and an amide functionality (N,N-dimethyl formyl group) were synthesized starting from a wide range of chalcones in moderate to good yields with excellent diastereoselectivity.
- Devi, E. Sankari,Pavithra, Thangavel,Tamilselvi,Nagarajan, Subbiah,Sridharan, Vellaisamy,Maheswari, C. Uma
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supporting information
p. 3576 - 3580
(2020/04/20)
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- Antiproliferative effects of chalcones on T cell acute lymphoblastic leukemia-derived cells: Role of PKCβ
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In this study, a series of 20 chalcone derivatives was synthesized, and their antiproliferative activity was tested against the human T cell acute lymphoblastic leukemia-derived cell line, CCRF-CEM. On the basis of the structural features of the most active compounds, a new library of chalcone derivatives, according to the structure–activity relationship design, was synthesized, and their antiproliferative activity was tested against the same cancer cell line. Furthermore, four of these derivatives (compounds 3, 4, 8, 28), based on lower IC50 values (between 6.1 and 8.9 μM), were selected for further investigation regarding the modulation of the protein expression of RACK1 (receptor for activated C kinase), protein kinase C (PKC)α and PKCβ, and their action on the cell cycle level. The cell cycle analysis indicated a block in the G0/G1 phase for all four compounds, with a statistically significant decrease in the percentage of cells in the S phase, with no indication of apoptosis (sub-G0/G1 phase). Compounds 4 and 8 showed a statistically significant reduction in the expression of PKCα and an increase in PKCβ, which together with the demonstration of an antiproliferative role of PKCβ, as assessed by treating cells with a selective PKCβ activator, indicated that the observed antiproliferative effect is likely to be mediated through PKCβ induction.
- Corsini, Emanuela,Facchetti, Giorgio,Esposito, Sara,Maddalon, Ambra,Rimoldi, Isabella,Christodoulou, Michael S.
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- 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
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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.
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- Donor-acceptor fluorophores as efficient energy transfer photocatalysts for [2 + 2] photodimerization
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Mild [2 + 2] photodimerization of enone substrates was induced by donor-acceptor fluorophores. Enone substrates were activated efficiently for anti-head to head dimerizations with a high yield (up to 83%) and high selectivity. The adjustable excited state potential also allows donor-acceptor fluorophores to be used for isomerization of the above substrates, confirming the potential of donor-acceptor fluorophores as energy transfer photocatalysts.
- Chen, Feng,Chen, Hao,Liu, Xue-Fen,Luo, Shu-Ping,Ren, Chen-Chao,Wu, Qing-An,Xu, Liang-Xuan,Yu, Xiao-Cong
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p. 3707 - 3716
(2020/06/03)
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- Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts
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A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading.
- Jurczak, Janusz,Majdecki, Maciej,Tyszka-Gumkowska, Agata
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supporting information
(2020/11/13)
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- Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes
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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.
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supporting information
p. 2307 - 2311
(2019/04/10)
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- Alkylation of Indoles with α,β-Unsaturated Ketones using Alumina in Hexanes
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We evaluated the influence of solvent on the alumina-promoted C3-alkylation of indoles with α,β-unsaturated ketones. We found that lipophilic solvents were generally superior to hydrophilic ones with hexanes offering the 3-alkyl indole products in high yields. Thus, we demonstrate an inexpensive and procedurally simple new process that pairs acidic alumina with hexanes to achieve this important Michael alkylation. The substrate scope includes twenty-four examples with reaction yields ranging from 61 to 96%. (Figure presented.).
- Zhang, Xiong,Jones-Mensah, Ebenezer,Deobald, Jackson,Magolan, Jakob
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supporting information
p. 5548 - 5551
(2019/11/19)
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- Evaluation of sulphonamide derivatives acting as inhibitors of human carbonic anhydrase isoforms I, II and Mycobacterium tuberculosis β-class enzyme Rv3273
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A series of novel sulphonamide derivatives was obtained from sulphanilamide which was N4-alkylated with ethyl bromoacetate followed by reaction with hydrazine hydrate. The hydrazide obtained was further reacted with various aromatic aldehydes. The novel sulphonamides were characterised by infrared, mass spectrometry, 1H- and 13C-NMR and purity was determined by high-performance liquid chromatography (HPLC). Human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and II and Mycobacterium tuberculosis β-CA encoded by the gene Rv3273 (mtCA 3) inhibition activity was investigated with the synthesised compounds which showed promising inhibition. The KIs were in the range of 54.6 nM–1.8 μM against hCA I, in the range of 32.1 nM–5.5 μM against hCA II and of 127 nM–2.12 μM against mtCA 3.
- Wani, Tanvi V.,Bua, Silvia,Khude, Pravin S.,Chowdhary, Abdul H.,Supuran, Claudiu T.,Toraskar, Mrunmayee P.
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p. 962 - 971
(2018/05/29)
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- General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible-Light Catalysis
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[2+2] Photocycloaddition, for example, the dimerization of chalcones and cinnamic acid derivatives, is a unique strategy to construct cyclobutanes, which are building blocks for a variety of biologically active molecules and natural products. However, most attempts at the above [2+2] addition have focused on solid-state, molten-state, or host–guest systems under ultraviolet-light irradiation in order to overcome the competition of facile geometric isomerization of nonrigid olefins. We report a general and simple method to realize the intermolecular [2+2] dimerization reaction of these acyclic olefins to construct cyclobutanes in a highly regio- and diastereoselective manner in solution under visible light, which provides an efficient solution to a long-standing problem.
- Lei, Tao,Zhou, Chao,Huang, Mao-Yong,Zhao, Lei-Min,Yang, Bing,Ye, Chen,Xiao, Hongyan,Meng, Qing-Yuan,Ramamurthy, Vaidhyanathan,Tung, Chen-Ho,Wu, Li-Zhu
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supporting information
p. 15407 - 15410
(2017/11/13)
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- Silver-catalyzed decarboxylative cross-coupling of α-keto acids with alkenes giving approach to chalcones
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A silver-catalyzed decarboxylative cross-coupling of α-keto acids with alkenes is reported. The method, with a wide range of substrate tolerance and mild operational conditions, can produce various chalcone derivatives in moderate to high yields from easily available starting materials.
- Wu, Shang,Yu, Hongheng,Hu, Qinzheng,Yang, Quanlu,Xu, Shouwang,Liu, Tian
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p. 4763 - 4765
(2017/12/01)
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- Domino-Fluorination-Protodefluorination Enables Decarboxylative Cross-Coupling of α-Oxocarboxylic Acids with Styrene via Photoredox Catalysis
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Domino-fluorination-protodefluorination decarboxylative cross-coupling of α-keto acids with styrene has been developed via photoredox catalysis. The critical part of this strategy is the formation of the carbon-fluorine (C-F) bond by the capture of a carbon-centered radical intermediate, which will overcome side reactions during the styrene radical functionalization process. Experimental studies have provided evidence indicating a domino-fluorination-protodefluorination pathway with α-keto acid initiating the photoredox cycle. The present catalytic protocol also affords a novel approach for the construction of α,β-unsaturated ketones under mild conditions.
- Zhang, Muliang,Xi, Junwei,Ruzi, Rehanguli,Li, Nan,Wu, Zhongkai,Li, Weipeng,Zhu, Chengjian
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p. 9305 - 9311
(2017/09/25)
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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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- 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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- Direct Regioselective [3 + 2]-Cyclization Reactions of Ambivalent Electrophilic/Nucleophilic β-Chlorovinyl Dithianes: Access to Cyclopentene Derivatives
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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
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supporting information
p. 5086 - 5089
(2016/10/14)
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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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- 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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- 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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- Synthesis of some novel hydrazone and 2-pyrazoline derivatives: Monoamine oxidase inhibitory activities and docking studies
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A novel series of 2-pyrazoline and hydrazone derivatives were synthesized and investigated for their human monoamine oxidase (hMAO) inhibitory activity. All compounds inhibited the hMAO isoforms (MAO-A or MAO-B) competitively and reversibly. With the exce
- Evranos-Aks?z, Begüm,Yabano?lu-?ift?i, Samiye,U?ar, Gülberk,Yelek?i, Kemal,Ertan, Rahmiye
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supporting information
p. 3278 - 3284
(2014/07/22)
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- Synthesis and anticancer activity evaluation of resveratrol-chalcone conjugates
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A series of novel resveratrol-chalcone conjugates have been synthesized. Four compounds were evaluated for their anticancer activity against 60 human cancer cell lines. Among all the derivatives, compound 70 was found to be the most active and showed high
- Kumar, Deepak,Raj, K. Kranthi,Malhotra, Sanjay V.,Rawat, Diwan S.
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supporting information
p. 528 - 535
(2014/04/17)
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- Design, synthesis and biological evaluation of pyrazolyl-thiazolinone derivatives as potential EGFR and HER-2 kinase inhibitors
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A series of pyrazolyl-thiazolinone derivatives (E1-E36) have been designed and synthesized and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Thirty-four of the 36 compounds were reported for the first time. Among them, compound 2-(5-(4-bromophenyl)-3-p-tolyl-4,5- dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (E28) displayed the most potent inhibitory activity (IC50 = 0.24 μM for EGFR and IC50 = 1.07 μM for HER-2). Antiproliferative assay results indicated that compound E28 owned high antiproliferative activity against MCF-7, B16-F10 and HCT-116 in vitro, with IC50 value of 0.30, 0.54, and 0.70 μM, respectively. Docking simulation was further performed to position compound E28 into the EGFR active site to determine the probable binding model. Based on the preliminary results, compound E28 with potent inhibitory activity in tumor growth would be a potential anticancer agent.
- Qiu, Ke-Ming,Wang, Hai-Hong,Wang, Li-Ming,Luo, Yin,Yang, Xian-Hui,Wang, Xiao-Ming,Zhu, Hai-Liang
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experimental part
p. 2010 - 2018
(2012/05/04)
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- Cytotoxic, DNA interaction, SOD mimic, and antimicrobial activities of square pyramidal copper(II) complexes
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The copper(II) complexes with NS donor ligand and ciprofloxacin were synthesized. The synthesized complexes were characterized by physicochemical parameters like elemental and thermal analysis, electronic, FT-IR, and LC-MS spectroscopy. The complexes were
- Patel, Mohan N.,Patel, Chintan R.,Joshi, Hardik N.
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scheme or table
p. 1224 - 1232
(2012/08/13)
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- Synthesis, characterization and pharmacological study of 4,5-dihydropyrazolines carrying pyrimidine moiety
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A series of 5-bromo-2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine were prepared under conventional heating as well as microwave reaction condition. The newly synthesized compounds were characterized on the basis of elemental, spectral and single crystal X-ray studies. These new compounds were screened for their antioxidant, anti-inflammatory and analgesic activities. Some of these compounds exhibited potent biological activities compared to the standard drug.
- Adhikari, Adithya,Kalluraya, Balakrishna,Sujith, Kizhakke Veedu,Gouthamchandra, Kuluvar,Jairam, Ravikumar,Mahmood, Riaz,Sankolli, Ravish
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p. 467 - 474
(2012/11/07)
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- Synthesis and selective inhibitory activity against human COX-1 of novel 1-(4-substituted-thiazol-2-yl)-3,5-di(hetero)aryl-pyrazoline derivatives
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Novel 1-(4-ethyl carboxylate-thiazol-2-yl)-3,5-di(hetero)aryl-2-pyrazoline derivatives were obtained by reacting 3,5-di(hetero)aryl-1-thiocarbamoyl-2- pyrazolines with the ethyl ester of α-bromo-pyruvic acid. The synthesized compounds were confirmed by spectroscopic data and assayed to evaluate their in vitro ability to inhibit both isoforms of human cyclooxygenase (hCOX). Some derivatives (compounds 5, 6, 13, 16, and 17) displayed promising selectivity against hCOX-1 in the micromolar range and were shown to have a selectivity index similar or better than the reference drugs (indometacin, diclofenac). The introduction of a phenyl or a 4-F-phenyl ring on the C5 associated with a 4-substituted phenyl or a heteroaryl group on the C3 of (4-substituted-thiazol- 2-yl)pyrazoline derivatives improved the activity against hCOX-1. Thanks to these preliminary results it could be possible to extend our knowledge of the pharmacophoric requirements for the discovery of new pyrazoline-based hCOX-1 inhibitors. Novel 1-(4-ethyl carboxylate-thiazol-2-yl)-3,5-di(hetero)aryl-2- pyrazoline derivatives were obtained by reacting 3,5-di(hetero)aryl-1- thiocarbamoyl-2-pyrazolines with the ethyl ester of α-bromo-pyruvic acid. Some derivatives displayed promising selectivity against human cyclooxygenase 1 (hCOX-1) in the micromolar range, with a selectivity index similar or better than the reference drugs, indometacin and diclofenac. Copyright
- Carradori, Simone,Secci, Daniela,Bolasco, Adriana,De Monte, Celeste,Yá?ez, Matilde
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p. 973 - 979
(2013/02/23)
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- Synthesis and in vitro evaluation of novel tetrazole embedded 1,3,5-trisubstituted pyrazoline derivatives as Entamoeba histolytica growth inhibitors
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A series of pyrazoline derivatives (1a-15a) was synthesized by cyclization of chalcones (1-15) with 2-[5-(4-methoxyphenyl)-1H-tetrazol-1-yl]acetohydrazide under basic conditions and were screened in vitro, to find out effect on the growth of HM1: IMSS strain of Entamoeba histolytica. The compounds 3a, 4a, 11a, 13a and 14a showed encouraging results with IC50 value in the range of 0.86-1.28 μM. However compound 13a showed most promising results with IC50 = 0.86 μM which is half of the metronidazole, the standard drug used for protozoal infection. Cell viability test in human hepatocellular carcinoma cell line (HepG2) revealed non-toxic nature of new synthesized compounds. Safety index calculations prevailed compound 13a as highly antiamoebic and least cytotoxic (S.I. = >116.28), almost twice than metronidazole.
- Wani, Mohmmad Younus,Bhat, Abdul Roouf,Azam, Amir,Lee, Dae Hyung,Choi, Inho,Athar, Fareeda
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experimental part
p. 845 - 854
(2012/09/11)
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- Allylic activation across an Ir-Sn heterobimetallic catalyst: Nucleophilic substitution and disproportionation of allylic alcohol
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A nucleophilic substitution of allylic alcohols with carbon (arene, heteroarene, allyltrimethylsilane, and 1,3-dicarbonyl compound), sulfur (thiol), oxygen (alcohol), and nitrogen (sulfonamide) nucleophiles has been demonstrated using an in house developed [Ir(COD)(SnCl3)l(μ-Cl)]2 heterobimetallic catalyst in 1,2-dichloroethane to afford the corresponding allylic products in moderate to excellent yields. In 4-hydroxycoumarin, allylation occurs at the 3-position. The diaryl-substituted allylic alcohols undergo disproportionation in presence of the heterobimetallic catalyst to provide the corresponding alkenes and chalcones. An electrophilic mechanism is proposed from Hammett correlation study.
- Chatterjee, Paresh Nath,Roy, Sujit
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supporting information; experimental part
p. 3776 - 3785
(2012/07/14)
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- Synthesis of some novel benzofuran-2-yl(4,5-dihyro-3,5-substituted diphenylpyrazol-1-yl) methanones and studies on the antiproliferative effects and reversal of multidrug resistance of human MDR1-gene transfected mouse lymphoma cells in vitro
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A new series of benzofuran-2-yl(4,5-diydro-3,5-substituted diphenylpyrazol-1-yl) methanone derivatives 8a-x by the reaction of the benzofuran-2-carbohydrazides 7 with various chalcone derivatives 3a-x using microwave irradiation has been described. The effect of synthesized compounds 8a-v was studied against human cancer cell lines for their antiproliferative activity and reversal of multidrug resistance on human MDR1-gene transfected mouse lymphoma cells. Among the 24 compounds, the 8c and 8h showed good antiproliferative activity 8b, 8f and 8k were exhibited good MDR reversal activity. The main significance of the process is easy workup process, short reaction time and high yield of the new compounds for biological interest. However, the studies on genetically modified multidrug resistant cancer cells are costly and time consuming.
- Parekh, Shrey,Bhavsar, Dhairya,Savant, Mahesh,Thakrar, Shailesh,Bavishi, Abhay,Parmar, Manisha,Vala, Hardevsinh,Radadiya, Ashish,Pandya, Nilay,Serly, Juliana,Molnár, Joseph,Shah, Anamik
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scheme or table
p. 1942 - 1948
(2011/04/26)
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- Activated fly ash catalyzed facile synthesis of novel spiro imidazolidine derivatives as potential antibacterial and antifungal agents
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An array of novel spiro imidazolidine derivatives was synthesized in dry media and was screened for their anti-microbial activities. Structure-activity relationship results revealed that compounds 22, 23 against P.aeruginosa, 24 against S.aureus, 24, 25 against K.pneumonia, 27 against S.aureus, β-H.streptococcus, 29 against M.luteus, K.pneumonia, 29, 30 against P.vulgaris exhibited excellent antibacterial activity at a minimum inhibitory concentration (MIC) value of 6.25 μg/mL. Compound 23 against M.gypseum, 25, 29 against Candida 6 and 29, 30 against C.albicans revealed excellent antifungal activity at a MIC value of 6.25 μg/mL.
- Kanagarajan,Thanusu,Gopalakrishnan
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scheme or table
p. 280 - 287
(2011/10/18)
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- Synthesis, spectral analysis, and in vitro microbiological evaluation of ethyl 7,9-diaryl-1, 4-diazaspiro[4.5]dec-9-ene-6-carboxylates as a new class of antibacterial and antifungal agents
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A series of novel ethyl 7,9-diaryl-1,4-diazaspiro[4.5]dec-9-ene-6- carboxylates was synthesized by the reaction of ethyl 4,6-diaryl-2-oxocyclohex- 3-ene-1-carboxylates with ethylenediamine in the presence of p-toluenesulfonic acid without a solvent under focused microwave irradiation. The title compounds were screened for their antimicrobial activities against a spectrum of clinically isolated microorganisms.
- Thanusu,Kanagarajan,Gopalakrishnan
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body text
p. 575 - 583
(2012/01/19)
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- Design, synthesis, and structure-activity relationships of pyrazole derivatives as potential FabH inhibitors
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Fatty acid biosynthesis is essential for bacterial survival. FabH, β-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and -negative bacteria. Fifty-six 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives were synthesized and developed as potent inhibitors of FabH. This inhibitor class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 1-(5-(4-fluorophenyl)- 3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone (12) and 1-(5-(4-chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone (13) were potent inhibitors of E. coli FabH.
- Lv, Peng-Cheng,Sun, Juan,Luo, Yin,Yang, Ying,Zhu, Hai-Liang
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scheme or table
p. 4657 - 4660
(2010/09/16)
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- Synthesis, characterization, antiamoebic activity and cytotoxicity of novel series of pyrazoline derivatives bearing quinoline tail
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The cyclization of chalcones (1a-1j) with 2-(quinolin-8-yloxy) acetohydrazide (2) under basic condition led to the formation of new compounds, pyrazoline derivatives (3a-3j). In vitro antiamoebic activity was performed against HM1: IMSS strain of Entamoeba histolytica. The results showed that the compounds 3d, 3g, 3h, and 3j exhibited promising antiamoebic activity (IC 50 = 0.05 μM, 0.31 μM, 0.06 μM, 0.29 μM) respectively than the standard drug metronidazole (IC50 = 1.84 μM). The toxicological studies of these compounds on human breast cancer MCF-7 cell line showed that all the compounds 3d, 3g, 3h, 3j and metronidazole were nontoxic at the concentration range of 1.56-50 μM.
- Hayat, Faisal,Salahuddin, Attar,Umar, Sadiq,Azam, Amir
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experimental part
p. 4669 - 4675
(2010/10/19)
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- Multicomponent synthesis of 3,5-diaryl-2,6-dicyanoanilines under thermal solvent-free conditions
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A facile parallel synthesis of 3,5-diaryl-2,6-dicyanoanilines via three-component reaction of aryl aldehydes, acetophenone derivatives, and malononitrile under thermal green solvent-free conditions in the presence of potassium carbonate and also potassium bicarbonate without using any hazardous materials is described.
- Shaterian, Hamid Reza,Honarmand, Moones,Oveisi, Ali Reza
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experimental part
p. 557 - 560
(2011/07/31)
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- Solution-phase parallel synthesis of substituted chalcones and their antiparasitary activity against Giardia lamblia
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A library of 25-membered chalcones was prepared by parallel synthesis. Substituted acetophenones and benzaldehydes were condensed using the Claisen-Schmidt base-catalyzed aldol condensation. Several chalcones showed in vitro antiparasitic activity against Giardia lamblia. The highest activity observed for the IC50 values were 12.72, 15.05 and 15.31 μg/mL, respectively; these are potential leads for the development of antigiardial compounds.
- Montes-Avila, Julio,Diaz-Camacho, Sylvia P.,Sicairos-Felix, Josefina,Delgado-Vargas, Francisco,Rivero
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experimental part
p. 6780 - 6785
(2009/12/06)
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- Novel domino reactions of (Z,Z)-2,2'-thiobis(1,3-diarylprop-2-en-1-ones) with acetylacetone and ethyl acetoacetate: Stereoselective synthesis of highly functionalized dihydrofurans
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The domino reactions of (Z,Z)-2,2'-thiobis(1,3-diarylprop-2-en-1-ones) with acetylacetone and ethyl acetoacetate in the presence of sodium ethoxide afforded the corresponding 4,5-dihydrofurans stereoselectively in moderate yields presumably via a Michael
- Vinosha, Beer Mohamed,Renuga, Subbiah,Gnanadeebam, Michael,Perumal, Subbu,Lycka, Antonin
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experimental part
p. 2776 - 2788
(2009/12/06)
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- Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines
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2,4-Dichloro-5-fluorophenyl containing 7-arylidenetriazolothiadiazines were obtained by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto- 1,2,4-triazole with 2,3-dibromo-1,3-diarylpropan-1-ones, and also by the reaction of 4-amino-3-(2,4
- Karthikeyan, Mari S.,Holla, Bantwal S.,Shenoy, Shalini
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scheme or table
p. 707 - 716
(2009/07/25)
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- Antifungal activity of chalcones: A mechanistic study using various yeast strains
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We reported the synthesis, antifungal evaluation and study on substituent effects of 21 chalcones. A lot of genetically defined strains belonging to different yeast genera and species, namely Saccharomyces cerevisiae, Hansenula polymorpha and Kluyveromyces lactis, were used as test organisms. Concerning the mode of the antifungal action of chalcones it was shown that DNA was probably not the main target for the chalcones. It was revealed that the yeast's intracellular glutathione and cysteine molecules play significant role as defence barrier against the chalcone action. It was also shown that chalcones may react with some proteins involved in cell separation.
- Lahtchev,Batovska,Parushev,Ubiyvovk,Sibirny
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p. 2220 - 2228
(2008/12/23)
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- Study on the substituents' effects of a series of synthetic chalcones against the yeast Candida albicans
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A large series of chalcones were synthesized and studied for activity against Candida albicans. The SAR analysis showed that the antifungal activity was highly dependent on the substitution pattern of the aryl rings and correlated to a large extent with the ability of compounds to interact with sulfhydryl groups. The most active were the hydroxylated chalcones as their activity related to the location of the phenolic group in the aryl ring B as follows: o-OH > p-OH ~ 3,4-di-OH > m-OH. These and other correlations obtained strongly contribute to the knowledge for design of anticandidal chalcones.
- Batovska,Parushev,Slavova,Bankova,Tsvetkova,Ninova,Najdenski
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- A modified and convenient method for the preparation of N-phenylpyrazoline derivatives
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Ten new N-phenylpyrazoline derivatives have been synthesized in high yields by condensation of chalcones with phenylhydrazine in the presence of potassium carbonate in reflux conditions. The workup is simple and involves treatment with ice-cold water. As compared with the previous method a considerable increase in the reaction rate with better yields has been observed.
- Safaei-Ghomi,Bamoniri,Soltanian-Telkabadi
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p. 892 - 896
(2008/02/10)
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- Synthesis and biological evaluation of aromatic enones related to curcumin
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Curcumin, a natural product isolated from the spice turmeric, has been shown to exhibit a wide range of pharmacological activities including certain anti-cancer properties. It has been specifically shown to be an effective inhibitor of angiogenesis both in vitro and in vivo. Using curcumin as a lead compound for anti-angiogenic analog design, a series of structurally related compounds utilizing a substituted chalcone backbone have been synthesized and tested via an established SVR cell proliferation assay. The results have yielded a wide range of compounds that equal or exceed curcumin's ability to inhibit endothelial cell growth in vitro. Due to both their commercial availability and their fairly straightforward synthetic preparation, these low molecular weight compounds are attractive leads for developing future angiogenic inhibitors.
- Robinson, Thomas Philip,Hubbard IV, Richard B.,Ehlers, Tedman J.,Arbiser, Jack L.,Goldsmith, David J.,Bowen, J. Phillip
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p. 4007 - 4013
(2007/10/03)
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- Multiple substituent effects on 13C chemical shifts in phenylstyryl ketones: Applicability of interactive free energy relationship
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13C chemical shifts for 23 mono- and di-substituted phenyl styryl ketones have been determined. The shieldings and deshieldings are compared with previous results for other aromatic derivatives. Correlations of the 13C chemical shifts of vinyl carbons with Hammett σ parameters has been determined to provide a consistent picture of electronic effects transmitted through the carbon framework of the compounds studied. Slopes obtained from such Hammett's plots are termed as ρ, and using these 'ρ' values applicability of interactive free energy relationship to chemical shift values has been tested. The cross- interaction constants qx and qy values for C-α are found to be -1.02 and -1.20 and for C-β are -1.46 and -1.19.
- Annapoorna,Prasad Rao,Sethuram
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p. 1341 - 1345
(2007/10/03)
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- Solution phase synthesis of a spiro[pyrrolidine-2,3'-oxindole] library via a three component 1,3-dipolar cycloaddition reaction
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A combinatorial library of 26,500 spiro[pyrrolidine,-2,3-oxindoles] was prepared in a single-compound format by a facile intermolecular 1,3-dipolar cycloaddition. An azomethine ylide, generated by the decarboxylative condensation of an isatin 1 with an α-amino acid 2, was trapped by a transchalcone 3 to afford heterocycles of the general structure 4. The regio- and stereochemistry of a representative product was determined by single crystal X-ray structure.
- Fokas, Demosthenes,Ryan, William J.,Casebier, David S.,Coffen, David L.
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p. 2235 - 2238
(2007/10/03)
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- Clemmensen reduction. XII The synthesis and acidolysis of some diaryl-substituted cyclopropane-1,2-diols. The possible involvement of a cyclopropyl cation
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The generation of a number of 1,2-diarylcyclopropane-1,2-diols is reported. Reaction of these in situ with acid gives, primarily, an α,β-unsaturated ketone in which the aryl substituent attached to the double bond is that which is best able to stabilize a benzylic cation. It is proposed that the reaction proceeds by O-protonation of the cyclopropane- 1,2-diol, followed by loss of water and opening of the resulting cyclopropyl cation and final deprotonation. Such initial O-protonation contrasts with the C-protonation normally observed in the acidolysis of cyclopropanols and other dialkyl- and alkylaryl-cyclopropane-1,2-diols.
- Davis, Brian R.,Hinds, Mark G.
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p. 309 - 319
(2007/10/03)
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- Interactive free energy relationships for non-additive multiple substituent effects in base catalysed condensation of benzaldehydes with acetophenones: A kinetic study
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The base-catalysed condensation of benzaldehydes with acetophenones is enhanced by electron-withdrawing substituents in both starting compounds.The magnitude of ρ-value obtained for various substituents in the benzaldehyde moiety decreases with the introduction of electron-withdrawing groups in the para position of acetophenone moiety.
- Sondu, S.,Sethuram, B,Rao, T. Navaneeth
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