- Synthesis, characterization and application of β-cyclodextrin-silica nanocomposite as potential microvessel in nucleophilic substitution reaction of phenacyl halides
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In the present study, β-cyclodextrin-silica hybrid is synthesized as a novel, efficient and eco-friendly microvessel and solid-liquid phase-transfer catalyst. This molecular host system was applied for nucleophilic substitution reaction of phenacyl halide
- Kiasat, Ali Reza,Nazari, Simin
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- Indole-linked 1,2,3-triazole derivatives efficiently modulate COX-2 protein and PGE2 levels in human THP-1 monocytes by suppressing AGE-ROS-NF-kβ nexus
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Aims: AGEs augment inflammatory responses by activating inflammatory cascade in monocytes, and hence lead to vascular dysfunction. The current study aims to study a plausible role and mechanism of a new library of indole-tethered 1,2,3-triazoles 2-13 in A
- Aslam, Tooba,Basha, Fatima Z.,Choudhary, M. Iqbal,Iqbal, Shazia,Jahan, Humera,Khan, Maria Aqeel,Siddiqui, Nimra Naz
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- Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
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Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.
- Maulide, Nuno,Riomet, Margaux,Roller, Alexander,Zhang, Haoqi
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supporting information
(2020/03/24)
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- Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation
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A general procedure for the late-stage [11C], [13C] and [14C]carbon isotope labeling of cyclic carbamates is reported. This protocol allows the incorporation of carbon dioxide, the primary source of carbon-14 and carbon-11 radioisotopes, in a direct, cost-effective and sustainable manner. A disconnection/reconnection strategy, involving ring opening/isotopic closure, was also implemented.
- Del Vecchio, Antonio,Talbot, Alex,Caillé, Fabien,Chevalier, Arnaud,Sallustrau, Antoine,Loreau, Olivier,Destro, Gianluca,Taran, Frédéric,Audisio, Davide
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supporting information
p. 11677 - 11680
(2020/10/19)
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- Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents
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(+)-Usnic acid, a product of secondary metabolism in lichens, has displayed a broad range of biological properties such as antitumor, antimicrobial, antiviral, anti-inflammatory, and insecticidal activities. Interested by these pharmacological activities and to tap into its potential, we herein present the synthesis and biological evaluation of new usnic acid enaminone-conjugated 1,2,3-triazoles 10-44 as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone 8 with a terminal ethynyl moiety. It was further reacted with various azides A1-A35 under copper catalysis to give triazoles 10-44 in good yields. Among the synthesized compounds, saccharin derivative 36 proved to be the most active analogue, inhibiting Mycobacterium tuberculosis (Mtb) at an MIC value of 2.5 μM. Analogues 16 and 27, with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on Bacillus subtilis, with compounds 18 [3-(trifluoromethyl)phenacyl] and 29 (N-acylmorpholinyl) showing inhibitory concentrations of 41 and 90.7 μM, respectively, while they were inactive on the other tested bacterial strains. Overall, the study presented here is useful for converting natural (+)-usnic acid into antitubercular and antibacterial agents via incorporation of enaminone and 1,2,3-triazole functionalities.
- Bangalore, Pavan K.,Vagolu, Siva K.,Bollikanda, Rakesh K.,Veeragoni, Dileep K.,Choudante, Pallavi C.,Misra, Sunil,Sriram, Dharmarajan,Sridhar, Balasubramanian,Kantevari, Srinivas
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supporting information
p. 26 - 35
(2020/01/03)
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- Photocatalyst-Free Visible-Light Enabled Synthesis of Substituted Pyrroles from α-Keto Vinyl Azides
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An efficient photocatalyst-free visible light enabled synthesis of substituted pyrroles from α-keto vinyl azides (readily prepared via Knoevenagel condensation of phenacyl azides with 2-oxo-2H-chromene-3-carbaldehydes) was developed. The reaction proceeds
- Borra, Satheesh,Borkotoky, Lodsna,Newar, Uma Devi,Das, Babulal,Maurya, Ram Awatar
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supporting information
p. 3364 - 3368
(2020/07/13)
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- Imidazolium-Based Ionic Network as a Robust Heterogeneous Catalyst in Synthesis of Phenacyl Derivatives
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A new imidazolium-based poly(ionic liquid) has been synthesized and used as a robust heterogeneous catalyst for the preparation of phenacyl derivatives by an SN2 reaction of different phenacyl bromides with a broad range of nucleophiles. The products are obtained in high yields under mild conditions. The catalyst can be recycled efficiently.
- Kakesh,Sayyahi,Badri,Tahanpesar
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p. 1218 - 1220
(2019/07/16)
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- Facile synthesis of 1,2,3-triazole-fused indolo- and pyrrolo[1,4]diazepines, DNA-binding and evaluation of their anticancer activity
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A facile synthetic strategy has been developed for the generation of structurally diverse N-fused heterocycles. The formation of fused 1,2,3-triazole indolo and pyrrolodiazepines proceeds through an initial Knoevenagel condensation followed by intramolecu
- Gour, Jitendra,Gatadi, Srikanth,Pooladanda, Venkatesh,Ghouse, Shaik Mahammad,Malasala, Satyaveni,Madhavi,Godugu, Chandraiah,Nanduri, Srinivas
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supporting information
(2019/10/05)
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- Preparation method of alpha-azide arone derivative
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The invention relates to a preparation method of an alpha-azide arone derivative. The method comprises the steps that substituted styrene, azidotrimethylsilane and an oxidant are added into a Schlenkreaction flask, water is added to serve as a solvent, a
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Paragraph 0065-0067
(2019/06/12)
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- Synthesis of new bicarbazole-linked triazoles as non-cytotoxic reactive oxygen species (ROS) inhibitors
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Carbazole analogs 3 and 4 and a new library of bicarbazole-linked triazoles 6–11 were prepared via new synthetic methodology. Metal-catalyzed oxidative coupling reaction was utilized for the synthesis of bicarbazole acetylene 4 and different metals (Znsu
- Iqbal, Shazia,Khan, Maria A.,Ansari, Zulqarnain,Jabeen, Almas,Faheem, Aisha,Fazal-Ur-Rehman, Saba,Basha, Fatima Z.
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p. 2330 - 2341
(2019/07/05)
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- α-N-Heteroarylation and α-Azidation of Ketones via Enolonium Species
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Enolonium species, resulting from the umpolung of ketone enolates by Koser's hypervalent iodine reagents activated by boron trifluoride, react with a variety of nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4-5 h. Additionally, α-azidation of the enolonium species takes place using trimethylsilyl azide as a convenient source of azide nucleophile.
- More, Atul A.,Pathe, Gulab K.,Parida, Keshaba N.,Maksymenko, Shimon,Lipisa, Yuriy B.,Szpilman, Alex M.
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p. 2442 - 2447
(2018/02/23)
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- Enantioselective separation of (±)-β-hydroxy-1,2,3-triazoles by supercritical fluid chromatography and high-performance liquid chromatography
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This paper reports the enantioseparation of β-hydroxy-1,2,3-triazole derivatives, which present a broad range of biological properties, by supercritical fluid chromatography (SFC) and high-performance liquid chromatography techniques (HPLC). Polysaccharid
- Alvarenga, Natália,Porto, André L.M.,Barreiro, Juliana Cristina
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p. 890 - 899
(2018/04/30)
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- Visible-light-enabled oxyazidation of alkenes leading to α-azidoketones in air
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A new and facile visible-light-enabled method for the synthesis of α-azidoketones has been developed via oxyazidation of alkenes with TMSN3 in air at room temperature. A series of α-azidoketones could be easily and efficiently obtained in moder
- Wei, Wei,Cui, Huanhuan,Yue, Huilan,Yang, Daoshan
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supporting information
p. 3197 - 3202
(2018/07/29)
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- Visible-Light-Accelerated Copper(II)-Catalyzed Regio- and Chemoselective Oxo-Azidation of Vinyl Arenes
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The visible-light-accelerated oxo-azidation of vinyl arenes with trimethylsilylazide and molecular oxygen as stoichiometric oxidant was achieved. In contrast to photocatalysts based on iridium, ruthenium, or organic dyes, [Cu(dap)2]Cl or [Cu(dap)Cl2] were found to be unique for this transformation, which is attributed to their ability to interact with the substrates through ligand exchange and rebound mechanisms. CuII is proposed as the catalytically active species, which upon coordinating azide will undergo light-accelerated homolysis to form CuI and azide radicals. This activation principle (CuII-X→CuI+X.) opens up new avenues for copper-based photocatalysis.
- Hossain, Asik,Vidyasagar, Adiyala,Eichinger, Christian,Lankes, Christian,Phan, Jenny,Rehbein, Julia,Reiser, Oliver
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supporting information
p. 8288 - 8292
(2018/06/29)
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- Method for preparing alpha-azidoketone compounds based on photocatalysis
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The invention discloses a method for preparing alpha-azidoketone compounds based on photocatalysis. The method is based on a reaction formula shown in the description, wherein R is optionally-substituted aryl, heteroaryl or 1-12 carbon alkyl; R is o
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Paragraph 0170; 0171; 0172
(2018/10/11)
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- One-pot synthesis of α-bromo- and α-azidoketones from olefins by catalytic oxidation with in situ-generated modified IBX as the key reaction
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Simple one-pot protocols for the syntheses of α-bromoketones and α-azidoketones starting from olefins have been developed by employing catalytic oxidation of the intermediary bromohydrins with in situ-generated modified IBX as the key reaction. The improved procedure involves initial formation of bromohydrin by the reaction of olefin with NBS in acetonitrile-water mixture (1:1) at rt followed by oxidation with in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), produced in catalytic amounts from 3,4,5,6-tetramethyl-2-iodobenzoic and Oxone. α-Bromoketones are further converted in the same pot to the corresponding α-azidoketones using NaN3/NaHCO3. The one-pot conversions are versatile for a variety of olefins that include cyclic as well as acyclic aliphatic olefins and electron-rich and electron-deficient styrenes. Chemoselective bromohydroxylation of electron-rich double bond and subsequent oxidation to the α-bromoketone is demonstrated for a substrate that contains both electron-rich and deficient double bonds.
- Chandra, Ajeet,Parida, Keshaba Nanda,Moorthy, Jarugu Narasimha
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p. 5827 - 5832
(2017/09/09)
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- Integration of aqueous biphasic with magnetically recyclable systems: Polyethylene glycol-grafted Fe3O4 nanoparticles catalyzed phenacyl synthesis in water
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The present work trends to define an efficient phenacyl catalytic synthesis method employing a new nano-magnetite-supported organocatalyst. Polyethylene glycol (PEG) was bonded successfully onto silica coated ferrite and the resultant nanoparticles (PEG@SiO2@Fe3O4) characterized by fourier transform infrared spectroscopy (FT-IR), atomic force microscopy (AFM), thermal gravimetric analysis (TGA), vibrating sample magnetometry (VSM), energy dispersive X-ray analysis (EDAX) and X-ray diffraction (XRD) that exhibited a good catalytic activity in the reaction. The nanoparticles could be easily separated from the reaction mixture by an external magnet and reused in seven reaction cycles without significant loss of activity.
- Amini, Atefeh,Sayyahi, Soheil,Saghanezhad, Seyyed Jafar,Taheri, Narges
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- A Metalloregulated Four-State Nanoswitch Controls Two-Step Sequential Catalysis in an Eleven-Component System
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The nanomechanical switch 1 with its three orthogonal binding motifs—the zinc(II) porphyrin, azaterpyridine, and shielded phenanthroline binding station—is quantitatively and reversibly toggled back and forth between four different switching states by mea
- Gaikwad, Sudhakar,Goswami, Abir,De, Soumen,Schmittel, Michael
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supporting information
p. 10512 - 10517
(2016/08/24)
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- Synthesis of novel 5-[(1,2,3-triazol-4-yl)methyl]-1-methyl-3H-pyridazino[4,5-b]indol-4-one derivatives by click reaction and exploration of their anticancer activity
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A series of pyridazino[4,5-b]indole derivatives containing alkyl-, benzyl- and phenacyl-substituted 1,2,3-triazolylmethyl units was synthesized using click chemistry approach. All 30 compounds of the series were screened in vitro against four cancer cell lines, viz. breast cancer cells MDA-MB-231 and MCF 7, human primary glioblastoma U-87 and human neuroblastoma IMR-32 cell lines. Most of the compounds exhibited potent cancer cell growth inhibition activity at very low micromolar concentrations. The IC50 value of compounds 7v and 7x against human neuroblastoma IMR-32 cell line is 0.07 and 0.04 μM, respectively. Among the tested compounds, ten compounds showed IC50 value less than 1 μM against MDA-MB-231 cells, whereas against IMR-32 cells, nine compounds and, against U-87 cells, six compounds showed similar inhibition activity. Further, these molecules exhibited prominent binding affinity and docking scores in the molecular simulation study with the target enzyme PI3 kinase. Graphical Abstract: This paper illustrates the synthesis of new fused indole-pyridazinone derivatives containing substituted 1,2,3-triazoles via click chemistry approach. Most of the compounds exhibited potent cancer cell growth inhibition activity at very low micromolar concentrations. [Figure not available: see fulltext.]
- Panathur, Naveen,Gokhale, Nikhila,Dalimba, Udayakumar,Koushik, Pulla Venkat,Yogeeswari, Perumal,Sriram, Dharmarajan
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p. 135 - 148
(2016/01/25)
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- Synthesis of ionic liquid-supported hypervalent iodine reagent and its application as a 'catch and release' reagent for α-substituted acetophenones
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A novel imidazolium-based ionic liquid-supported hypervalent iodine reagent has been synthesized and employed for a 'catch and release' strategy with substituted acetophenones to generate various α-substituted acetophenones in good to excellent yields. The use of an ionic liquid-supported hypervalent iodine reagent avoids chromatographic separation for the purification of α-substituted acetophenones and thus makes the method greener.
- Muthyala, Manoj Kumar,Choudhary, Sunita,Kumar, Anil
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p. 14297 - 14303
(2014/04/17)
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- Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles
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As resoluc?o?es cine?ticas de (±)-β- azidofeniletano?is foram realizadas usando a lipase de Candida antarctica fornecendo os compostos enantiomericamente enriquecidos, (R)-β- azidofeniletano?is e acetato de (S)-β-azidofeniletila em bons excessos enantiome
- Rocha, Lenilson C.,Rosset, Isac G.,Melgar, Gliseida Z.,Raminelli, Cristiano,Porto, Andre? L. M.,Jeller, Alex H.
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p. 1427 - 1432
(2013/09/24)
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- Coupling biocatalysis and click chemistry: One-pot two-step convergent synthesis of enantioenriched 1,2,3-triazole-derived diols
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A fully convergent one-pot two-step synthesis of different chiral 1,2,3-triazole-derived diols in high yields and excellent enantio- and diastereoselectivities has been achieved under very mild conditions in aqueous medium by combining a single alcohol dehydrogenase (ADH) with a Cu-catalysed 'click' reaction. The Royal Society of Chemistry 2013.
- Cuetos, Aníbal,Bisogno, Fabricio R.,Lavandera, Iván,Gotor, Vicente
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supporting information
p. 2625 - 2627
(2013/04/23)
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- β-cyclodextrin immobilized onto dowex resin: A unique microvessel and heterogeneous catalyst in nucleophilic substitution reactions
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The catalytic activity of β-cyclodextrin immobilized on Dowex resin as an efficient solid-liquid phase transfer catalyst was developed for the synthesis of alkyl thiocyanates and phenacyl derivatives in water. The nucleophilic substitution reactions were performed under mild reaction condition and gave the products in excellent yields. Furthermore, the catalyst could be recycled by facile separation without any loss of activity.
- Kiasat, Ali Reza,Zarinderakht, Nasrollah,Sayyahi, Soheil
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experimental part
p. 699 - 702
(2012/05/05)
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- Cis-1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate as an efficient reagent for the synthesis of phenacyl thiocyanates and phenacyl azides
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Styrenes efficiently undergo thiocyanation and azidation with cis-1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate at 0C to furnish the corresponding thiocyanatoketones and azidoketones. This method is a direct, one-pot synthesis under mild condition using methanol as solvent.
- Badri, Rashid,Gorjizadeh, Maryam
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experimental part
p. 2058 - 2066
(2012/06/04)
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- An efficient method for synthesis of phenacyl derivatives under homogeneous phase transfer catalyst condition in aqueous media
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In this letter, a mild and efficient procedure for synthesis of phenacyl derivatives under homogenous catalysis in the presence of tetrabutylammonium bromide in aqueous media is described. The nucleophilic substitution reactions were performed under ecofriendly conditions and gave the corresponding products in high yields and short reaction times.
- Sayyahi, Soheil,Saghanezhad, Jafar
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experimental part
p. 300 - 302
(2012/01/14)
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- A simple and efficient PTT-mediated synthesis of a-azidoketones in [bmim][BF4] ionic liquid
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A simple and efficient one-pot method has been described for the direct synthesis of α-azidoketones from various ketones possessing a-hydrogen by reaction with phenyltrimethylammonium tribromide (PTT) and subsequent treatment with NaN3 in ionic liquid. The procedure gives high yield and the ionic liquid can be reused.
- Kumar, Anil,Ahmed, Israr,Rao,Patel, Gautam,Kumar, Dalip
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experimental part
p. 611 - 616
(2009/12/06)
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- Synthesis of optically pure 2-azido-1-arylethanols with isolated enzymes and conversion to triazole-containing β-blocker analogues employing click chemistry
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(Chemical Equation Presented) Both antipodes of 2-azido-1-arylethanols were synthesized with excellent optical purity via enzymatic reduction of the corresponding α-azidoacetophenone derivatives catalyzed by a recombinant carbonyl reductase from Candida m
- Ankati, Haribabu,Yang, Yan,Zhu, Dunming,Biehl, Edward R.,Hua, Ling
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p. 6433 - 6436
(2008/12/22)
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- Synthesis, monoamine transporter binding, properties, and functional monoamine uptake activity of 3β-[4-methylphenyl and 4-chlorophenyl]- 2β-[5-(substituted phenyl)thiazol-2-yl]tropanes
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Synthetic methods were developed for the synthesis of the 3β-(4-substituted phenyl)-2β-[5-(substituted phenyl)thiazol-2-yl] tropanes (4a-s). The compounds were evaluated for their monoamine transporter binding and monoamine uptake inhibition properties using both rat brain tissue and cloned transporter assays. In general, the compounds showed higher dopamine transporter (DAT) affinity relative to the serotonin and norepinephrine transporters (SERT and NET, respectively) and greater [3H]dopamine uptake inhibition potency relative to [3H]serotonin and [ 3H]norepinephrine uptake inhibition. Several compounds were DAT selective relative to the SERT and NET in the monoamine transporter binding assays. The most potent and selective analog in the functional monoamine uptake inhibition test was 3β-(4-methylphenyl-2β-[5-(3-nitrophenyl)thiazol-2- yl]tropane (4p).
- Gong, Paul K.,Blough, Bruce E.,Brieaddy, Lawrence E.,Huang, Xiaodong,Kuhar, Michael J.,Navarro, Hernán A.,Carroll, F. Ivy
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p. 3686 - 3695
(2008/02/10)
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- A fast procedure for the preparation of vicinal azidoalcohols using polymer supported reagents
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Several vicinal azidoalcohols were prepared in good to high yield and purity, starting from aryl α-haloketones, using reagents supported on a macroporous ion exchange resin. This is a fast and new approach to aryl azidoalcohols.
- Souza Brenelli, Eugênia Cristina,Brenelli, José Afranio,Laranjeira Pinto, Raquel Cristina
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p. 4531 - 4533
(2007/10/03)
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- Base-induced coupling of α-azido ketones with aldehydes -an easy and efficient route to trifunctionalized synthons 2-azido-3-hydroxy ketones, 2-acylaziridines, and 2-acylspiroaziridines
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An improved synthesis of a-azido ketones under phase-transfer conditions has been developed. The transformation of α-azido ketones into acyclic and heterocyclic 2-azido-3-hydroxy ketones has been demonstrated and the relative configurations of the chroman
- Patonay, Tamas,Juhasz-Toth, Eva,Benyei, Attila
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p. 285 - 295
(2007/10/03)
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