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Zeitschriftenartikel zum Thema „Huisgen 1“

Autor: Grafiati

Veröffentlicht am 4. Juni 2021

Zuletzt aktualisiert am 27. Juli 2025

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1

Watt, Jacinta A., Carlie T. Gannon, Karen J. Loft, Zoran Dinev, and Spencer J. Williams. "'Click' Preparation of Carbohydrate 1-Benzotriazoles, 1,4-Disubstituted, and 1,4,5-Trisubstituted Triazoles and their Utility as Glycosyl Donors." Australian Journal of Chemistry 61, no. 11 (2008): 837. http://dx.doi.org/10.1071/ch08364.

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Glycosyl triazoles can be prepared from readily available anomeric azides through various ‘click’ methodologies: thermal Huisgen cycloaddition with alkynes, strain-promoted Huisgen cycloaddition of benzynes, and CuI-catalyzed azide-alkyne cycloaddition of terminal alkynes (CuAAC reaction). Here we investigate the formation of glycosyl 1-benzotriazoles from anomeric and non-anomeric carbohydrate azides using benzynes derived from substituted anthranilic acids. The reactivity of the resulting anomeric 1-benzotriazoles as glycosyl donors was investigated and compared with 1,4-disubstituted glycos

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2

Blanco-Carapia, Roberto E., Julio C. Flores-Reyes, Yizrell Medina-Martínez, et al. "Synthesis of New bis 1- and 5-Substituted 1H-Tetrazoles via Huisgen-Type 1,3-Dipolar Cycloadditions." Proceedings 9, no. 1 (2019): 32. http://dx.doi.org/10.3390/ecsoc-22-05780.

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The synthesis and characterization of one symmetrical bis-1-substituted-1H-tetrazole (69%) via a Huisgen-type 1,3-dipolar cycloaddition, as well as, one symmetrical aza-linked bis-5-substituted-1H-tetrazole (57%) via a classic Huisgen 1,3-dipolar cycloaddition followed by a reductive aza-coupling under greener reaction conditions are described. The main reason behind these tetrazole-based ligands is to construct novel Metal-Organic Framework (MOF) architectures to evaluate their CO2 capture properties under relative humidity conditions. It is worthy to note that both herein reported products h

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3

Luo, Han, Yong-Feng Lv, Hong Zhang, Jiang-Miao Hu, Hong-Mei Li, and Shou-Jin Liu. "Synthesis and Antitumor Activity of 1-Substituted 1,2,3-Triazole-Mollugin Derivatives." Molecules 26, no. 11 (2021): 3249. http://dx.doi.org/10.3390/molecules26113249.

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A new series of mollugin-1,2,3-triazole derivatives were synthesized using a copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated mollugin with aryl azides. All the compounds were evaluated for their cytotoxicity on five human cancer cell lines (HL-60, A549, SMMC-7721, SW480, and MCF-7) using MTS assays. Among the synthesized series, most of them showed cytotoxicity and most of all, compounds 14 and 17 exhibited significant cytotoxicity of all five cancer cell lines.

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4

Kroņkalne, Rasma, Rūdolfs Beļaunieks, and Māris Turks. "Synthesis of 4-(tert-Butyldimethylsilyl)-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine." Molbank 2022, no. 3 (2022): M1427. http://dx.doi.org/10.3390/m1427.

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SN2 rection between 4-(tert-butyldimethylsilyl)hex-5-yn-1-yl 4-methylbenzenesulfonate and NaN3 in DMF at 80 °C provided (6-azidohex-1-yn-3-yl)(tert-butyl)dimethylsilane intermediate, which underwent in situ intramolecular thermal Huisgen azide–alkyne cycloaddition reaction. This one-pot process gave 4-(tert-butyldimethylsilyl)-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine in 78% yield.

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5

M, Heravi; Majid, M. Dehghani, V. Zadsirjan, and M. Ghanbarian. "Alkynes as privileged synthons in selected organic name reactions." Current Organic Synthesis 16, no. 2 (2019): 205–43. https://doi.org/10.2174/1570179416666190126100744.

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Alkynes are actually basic chemicals, serving as privileged synthons for planning new organic reactions for assemblage of a reactive motif, which easily undergoes a further desirable transformation. Name reactions, in organic chemistry are referred to those reactions which are well-recognized and reached to such status for being called as their explorers, discoverers or developers. Alkynes have been used in various name reactions. In this review, we try to underscore the applications of alkynes as privileged synthons in prevalent name reactions such as Huisgen 1,3-dipolar cycloaddtion via Clic

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6

Zaki, Mohamed, Abdelouahd Oukhrib, Ahmed El Hakmaoui, Marie-Aude Hiebel, Sabine Berteina-Raboin, and Mohamed Akssira. "Synthesis of novel 1,2,3-triazole-substituted tomentosins." Zeitschrift für Naturforschung B 74, no. 3 (2019): 273–81. http://dx.doi.org/10.1515/znb-2018-0225.

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AbstractA series of 1,2,3-triazole-containing tomentosin scaffolds was obtained from tomentosin 1. The synthesis involved a Michael addition of trimethylsilylazide on the α-methylene-γ-lactone function of the natural sesquiterpene lactone 1 to give the diastereoisomers 2 and 3, which were readily separated by column chromatography. These compounds underwent copper-catalyzed Huisgen 1,3-dipolar cycloaddition with various terminal alkynes to provide compounds 4a–h and 5a–h in good yields.

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7

Kumar, K. S. Santhosh, B. Sreelakshmi, and C. P. Reghunadhan Nair. "Polytriazole-based shape memory composite by Huisgen 1, 3 dipolar polycycloaddition reaction." Materials Letters 137 (December 2014): 315–18. http://dx.doi.org/10.1016/j.matlet.2014.09.015.

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8

Arigela, Rajesh K., Sudhir K. Sharma, Brijesh Kumar, and Bijoy Kundu. "Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles." Beilstein Journal of Organic Chemistry 9 (February 19, 2013): 401–5. http://dx.doi.org/10.3762/bjoc.9.41.

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A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide–internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields.

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9

Jansa, Petr, Petr Špaček, Ivan Votruba, et al. "Efficient one-pot synthesis of polysubstituted 6-[(1H-1,2,3-triazol-1-yl)methyl]uracils through the “click” protocol." Collection of Czechoslovak Chemical Communications 76, no. 9 (2011): 1121–31. http://dx.doi.org/10.1135/cccc2011074.

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The preparation of several triazolo acyclic nucleosides and triazolo acyclic nucleoside phosphonates is described. The synthetic methodology has been developed as an efficient one-pot Cu(I)-catalyzed azide alkyne Huisgen “click” cycloaddition. A novel Cu(I)-catalyzed decarboxylation reaction of 1-substituted 1H-1,2,3-triazole-4-carboxylic acids at room temperature was observed and used for the preparation of 1-substituted 1H-1,2,3-triazoles. As congeners of TPI (Taiho pharmaceutical inhibitor), the prepared compounds were screened as potential inhibitors of human thymidine phosphorylase, but n

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Shkineva, T. K., O. V. Serushkina, I. A. Vatsadze, T. E. Khoranyan, and I. L. Dalinger. "Synthesis of 2,5-disubstituted pyrazolyl-1,3,4-oxadiazoles by the Huisgen reaction." Russian Chemical Bulletin 71, no. 8 (2022): 1737–44. http://dx.doi.org/10.1007/s11172-022-3584-1.

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11

Ritu, Mamgain, Atheaya Himanshu, I. Khan Shabana, Manohar Sunny, and S. Rawat Diwan. "Synthesis of novel 1,2,3-triazole incorporated quinoline derivatives via click chemistry and evaluation of their antimalarial activity." Journal of Indian Chemical Society Vol. 91, Aug 2014 (2014): 1443–50. https://doi.org/10.5281/zenodo.5728668.

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Department of Chemistry, University of Delhi, Delhi-110 007, India <em>E-mail </em>: dsrawat@chemistry.du.ac.in <em>Fax</em> : 91-11-27667501 b National Centre for Natural Products Research, University of Mississippi, Oxford, MS 38677, USA <em>Manuscript received 05 January 2014, accepted 15 January 2014</em> A series of structurally diverse novel 1,2,3-triazole incorporated quinoline derivatives (7a-g and 8a-l) were prepared via simple and efficient click chemistry involving Cu<sup>I</sup> catalyzed intermolecular Huisgen [3+2] cycloaddition reaction in good to excellent yields. All the synth

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12

Coghi, Paolo, Jerome P. L. Ng, Ali Adnan Nasim, and Vincent Kam Wai Wong. "N-[7-Chloro-4-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl]quinoline]-acetamide." Molbank 2021, no. 2 (2021): M1213. http://dx.doi.org/10.3390/m1213.

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The 1,2,3-triazole is a well-known biologically active pharmacophore constructed by the copper-catalyzed azide–alkyne cycloaddition. We herein reported the synthesis of 4-amino-7-chloro-based [1,2,3]-triazole hybrids via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of 4-azido-7-chloroquinoline with an alkyne derivative of acetaminophen. The compound was fully characterized by Fourier-transform infrared (FTIR), proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV) and high-resolution mass

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13

Gonçalves, Azambuja, Davi, et al. "Ethyl 6-Methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate." Molbank 2019, no. 3 (2019): M1076. http://dx.doi.org/10.3390/m1076.

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The Biginelli reaction is an acid-catalyzed, three-component reaction between an aldehyde, a hydrogen methylene active compound, and urea (or its analogue) and constitutes a rapid and easy synthesis of highly functionalized heterocycles. Synthesis of ethyl 6-methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate, identified by our laboratory code LaSOM® 293, was achieved using the Biginelli reaction as the key step, followed by the Huisgen 1,3-dipolar cycloaddition in a convergent four-step route. The product LaSOM® 293 was obtained with a

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14

Schollmeyer, Dieter, and Heiner Detert. "3-(4-Hexyloxyphenyl)-1,2,4-triazolo[3,4-b]benzothiazole." Acta Crystallographica Section E Structure Reports Online 70, no. 3 (2014): o247. http://dx.doi.org/10.1107/s1600536814002153.

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The title compound, C20H21N3OS, was prepared by Huisgen reaction of 5-(4-hexyloxyphenyl)tetrazole and chlorobenzothiazole. The essentially planar benzothiazolotriazole framework [maximum deviation from the mean plane of 0.077 (1) Å for the bridgehead N atom] and the phenyl ring form a dihedral angle of 53.34 (5)°. The hexyloxy chain adopts agauche–all-anti conformation. The intracentroid separation of 3.7258 (8) Å between the triazole and benzene rings is the closest contact between individual molecules in the crystal.

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15

Fall, Serigne Abdou Khadir, Sara Hajib, Oumaima Karai, et al. "Tetramethyl 1,1′-(2-[{4,5-bis(Methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate)." Molbank 2021, no. 1 (2021): M1186. http://dx.doi.org/10.3390/m1186.

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A new compound tetramethyl 1,1′-(2-[{4,5-bis(methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate) (3) was prepared in two steps starting from 2-((4-methylphenyl)sulfonamido)-2-((tosyloxy)methyl)propane-1,3-diylbis(4-methylbenzenesulfonate) (1), with an overall yield of 74%. The key step being the copper-free Huisgen cycloaddition between N-(1,3-diazido-2-(azidomethyl)propan-2-yl)-4-methylbenzenesulfonamide (2) and commercially available dimethyl acetylenedicarboxylate. The chemical structure of compound 3 was de

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Bhaskar, Srijanani, Kyung-Ho Roh, Xuwei Jiang, Gregory L. Baker, and Joerg Lahann. "Spatioselective Modification of Bicompartmental Polymer Particles and Fibers via Huisgen 1, 3-Dipolar Cycloaddition." Macromolecular Rapid Communications 29, no. 24 (2008): 1973. http://dx.doi.org/10.1002/marc.200800652.

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17

Liu, Wujun, Shuhua Hou, and Zongbao Kent Zhao. "Synthesis and electrochemical behavior of triazole-containing nicotinamide adenine dinucleotide analogs." Canadian Journal of Chemistry 88, no. 1 (2010): 35–41. http://dx.doi.org/10.1139/v09-145.

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The coupling of 2′,3′-di-O-acetyl nicotinamide mononucleotide with 3-butyn-1-ol in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride quantitatively afforded a terminal alkyne-containing intermediate. Furthermore, copper(I)-mediated Huisgen [3 + 2] cycloaddition with a series of azido compounds in a two-phase solvent system gave eight triazole-containing nicotinamide adenine dinucleotide analogs with yields over 88%. The cyclic voltammetric behaviors of these novel analogs were investigated with a glassy carbon electrode, and structural features of these analogs on their electrochemica

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18

Karbasi, Mohadeseh, Peyman Salehi, Atousa Aliahmadi, Morteza Bararjanian, and Farzaneh Zandi. "Synthesis of novel menthol derivatives containing 1,2,3-triazole group and their in vitro antibacterial activities." Journal of the Serbian Chemical Society, no. 00 (2023): 6. http://dx.doi.org/10.2298/jsc220813006k.

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New N-substituted ?-aminonitrile derivatives from menthol were synthesized by consecutive succinic ester formation, propargylation, 1,3-dipolar Huisgen cycloaddition and Strecker reaction. The structures of the synthesized compounds were confirmed by diverse spectroscopic techniques including 1HNMR, 13C-NMR, ESI-MS, and IR. The novel synthesized compounds were evaluated for their in vitro antibacterial activities against Staphylococcus aureus as Gram-positive and Escherichia coli as Gram-negative bacteria. These compounds demonstrated a strong inhibitory effect against S. aureus with the minim

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Amel Diab, Sonia, Antje Hienzch, Cyril Lebargy, Stéphane Guillarme, Emmanuel Pfund, and Thierry Lequeux. "Synthesis of fluorophosphonylated acyclic nucleotide analogues via copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition." Organic & Biomolecular Chemistry 7, no. 21 (2009): 4481. http://dx.doi.org/10.1039/b912724k.

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Kolyachkina, Svetlana V., Vitali I. Tararov, Cyril S. Alexeev, et al. "N6-substituted adenosines. Cytokinin and antitumor activities." Collection of Czechoslovak Chemical Communications 76, no. 11 (2011): 1361–78. http://dx.doi.org/10.1135/cccc2011114.

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A series of N6-adenosine derivatives were synthesized by alkylation of N6-acetyl-2′,3′,5′-tri-O-acetyladenosine (1) with alkyl halides and alcohols. It was shown that propargyl derivative 2a is a good substrate for copper(I) catalyzed Huisgen [3+2] cycloaddition with azides. This click-reaction can be used for preparation of the libraries of 1,2,3-triazolyl modified adenosines. Biological activities of N6-adenosines were studied in two plant and six human cancer cell assays. The remarkable parallel between cytokinin and cytotoxic activities was found. The most cytokinin active compounds 3c–3e

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El-Sheref, Essmat M., Mohammed A. I. Elbastawesy, Alan B. Brown, et al. "Design and Synthesis of (2-oxo-1,2-Dihydroquinolin-4-yl)-1,2,3-triazole Derivatives via Click Reaction: Potential Apoptotic Antiproliferative Agents." Molecules 26, no. 22 (2021): 6798. http://dx.doi.org/10.3390/molecules26226798.

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A mild and versatile method based on Cu-catalyzed [2+3] cycloaddition (Huisgen-Meldal-Sharpless reaction) was developed to tether 3,3’-((4-(prop-2-yn-1-yloxy)phenyl)methylene)bis(4-hydroxyquinolin-2(1H)-ones) with 4-azido-2-quinolones in good yields. This methodology allowed attaching three quinolone molecules via a triazole linker with the proposed mechanism. The products are interesting precursors for their anti-proliferative activity. Compound 8g was the most active one, achieving IC50 = 1.2 ± 0.2 µM and 1.4 ± 0.2 µM against MCF-7 and Panc-1 cell lines, respectively. Moreover, cell cycle an

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Yavari, Issa, Reza Hosseinpour, Ramin Pashazadeh, and Stavroula Skoulika. "ChemInform Abstract: Novel Synthesis of Functionalized Indolizine Derivatives from Huisgen′s Zwitterions and 1-Methylimidazole/Dichloroketene Adduct." ChemInform 43, no. 51 (2012): no. http://dx.doi.org/10.1002/chin.201251133.

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Saravanan, Nagarajan, Maruthapillai Arthanareeswari, Palanisamy Kamaraj, and Bitragunta Sivakumar. "Efficient synthesis via azide–alkyne Huisgen [3+2] cycloaddition reaction and antifungal activity studies of novel triazoloquinolines." Research on Chemical Intermediates 41, no. 8 (2014): 5379–88. http://dx.doi.org/10.1007/s11164-014-1638-1.

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Diz, Paula M., Alberto Coelho, Abdelaziz El Maatougui, et al. "Copper-Catalyzed Huisgen 1,3-Dipolar Cycloaddition under Oxidative Conditions: Polymer-Assisted Assembly of 4-Acyl-1-Substituted-1,2,3-Triazoles." Journal of Organic Chemistry 78, no. 13 (2013): 6540–49. http://dx.doi.org/10.1021/jo400800j.

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McCarroll, Andrew J., Charles S. Matthews, Geoffrey Wells, Tracey D. Bradshaw, and Malcolm F. G. Stevens. "Synthesis of antitumour (1H-1,2,3-triazol-4-yl)-4-hydroxycyclohexa-2,5-dien-1-ones by copper-catalysed Huisgen cycloadditions." Organic & Biomolecular Chemistry 8, no. 9 (2010): 2078. http://dx.doi.org/10.1039/b920039h.

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Kouznetsov, Vladimir V., Daniela Calderón Lamus, and Carlos E. Puerto Galvis. "Synthesis and Characterization of New Functionalized 1,2,3-Triazole-Based Acetaminophen Derivatives via Click Chemistry from Expired Commercial Acetaminophen Tablets." Reactions 4, no. 3 (2023): 329–41. http://dx.doi.org/10.3390/reactions4030020.

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We hereby describe an efficient method for the preparation of a series of new 1-substituted 1,2,3-triazole-based acetaminophen derivatives through a clean, good-yielding, simple, and expeditious procedure based on the O-propargylation reaction of the acetaminophen (APAP) obtained from expired commercial tablets and the CuBr(PPh3)3-catalyzed Huisgen reaction between O-propargylated APAP and diverse organoazides prepared from commercially available anilines as available starting reagents. An interesting nitric oxide-releasing 1,2,3-triazole hybrid of APAP was also obtained easily using the devel

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Khasiyatullina, Nadezhda R., Tamara A. Baronova, Ekaterina V. Mironova, et al. "Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes." Organic Chemistry Frontiers 5, no. 21 (2018): 3113–28. http://dx.doi.org/10.1039/c8qo00915e.

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Piškor, Martina, Astrid Milić, Sanja Koštrun, et al. "Synthesis, Antiproliferative Activity, and ADME Profiling of Novel Racemic and Optically Pure Aryl-Substituted Purines and Purine Bioisosteres." Biomolecules 15, no. 3 (2025): 351. https://doi.org/10.3390/biom15030351.

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The aim of this study was to synthesize new racemic and optically pure aryl-substituted purine bioisosteres using ultrasound-assisted Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition. Regioselective synthesis of α-azido alcohols was applied to afford heterocycles with a 2-hydroxyeth-1-yl linker. Catalytic asymmetric synthesis using halohydrin dehalogenase in the ring-opening of epoxides gave enantioenriched azido alcohols, which subsequently afforded R- and S-enantiomers of purine and pyrrolo[2,3-d]pyrimidines with a 1-hydroxyeth-2-yl linker. The newly synthesized compounds were evaluated in

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Pršir, Kristina, Ema Horak, Marijeta Kralj, et al. "Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl Derivatives." Molecules 27, no. 3 (2022): 637. http://dx.doi.org/10.3390/molecules27030637.

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In this work, a series of novel 1,2,3-triazolyl-coumarin hybrid systems were designed as potential antitumour agents. The structural modification of the coumarin ring was carried out by Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition of 7-azido-4-methylcoumarin and terminal aromatic alkynes to obtain 1,4-disubstituted 1,2,3-triazolyl-coumarin conjugates 2a–g, bis(1,2,3-triazolyl-coumarin)benzenes 2h–i and coumarin-1,2,3-triazolyl-benzazole hybrids 4a–b. The newly synthesised hybrid molecules were investigated for in vitro antitumour activity against five human cancer cell lines, colon carcin

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Özdemir, Zulal, Uladzimir Bildziukevich, Martina Čapková, et al. "Triterpenoid–PEG Ribbons Targeting Selectivity in Pharmacological Effects." Biomedicines 9, no. 8 (2021): 951. http://dx.doi.org/10.3390/biomedicines9080951.

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(1) Background: To compare the effect of selected triterpenoids with their structurally resembling derivatives, designing of the molecular ribbons was targeted to develop compounds with selectivity in their pharmacological effects. (2) Methods: In the synthetic procedures, Huisgen 1,3-dipolar cycloaddition was applied as a key synthetic step for introducing a 1,2,3-triazole ring as a part of a junction unit in the molecular ribbons. (3) Results: The antimicrobial activity, antiviral activity, and cytotoxicity of the prepared compounds were studied. Most of the molecular ribbons showed antimicr

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Canseco-González, Daniel, José Luis Rodríguez de la O, and José Enrique Herbert-Pucheta. "Combined XRD-paramagnetic 13C NMR spectroscopy of 1,2,3-triazoles for revealing copper traces in a Huisgen click-chemistry cycloaddition. A model case." Heterocyclic Communications 25, no. 1 (2019): 98–106. http://dx.doi.org/10.1515/hc-2019-0018.

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AbstractCopper-catalyzed Alkyne-Azide Cycloaddition (CuAAC) click chemistry robustness has been demonstrated over recent years to produce 1,2,3-triazoles with excellent yields at mild conditions with simple purification methods. However, the consequences of having copper paramagnetic traces in final products, which complicate spectroscopic assignments and can produce inaccurate conclusions, has been scarcely discussed. Herein we present a strategy that combines X-Ray Diffraction (XRD) with 13C- paramagnetic Nuclear Magnetic Resonance spectroscopy, in order to demonstrate the presence of parama

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Mamat, Constantin, Marc Pretze, Matthew Gott, and Martin Köckerling. "Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling." Beilstein Journal of Organic Chemistry 12 (November 21, 2016): 2478–89. http://dx.doi.org/10.3762/bjoc.12.242.

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Novel, functionalized piperazine derivatives were successfully synthesized and fully characterized by 1H/13C/19F NMR, MS, elemental analysis and lipophilicity. All piperazine compounds occur as conformers resulting from the partial amide double bond. Furthermore, a second conformational shape was observed for all nitro derivatives due to the limited change of the piperazine chair conformation. Therefore, two coalescence points were determined and their resulting activation energy barriers were calculated using 1H NMR. To support this result, single crystals of 1-(4-nitrobenzoyl)piperazine (3a,

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Pucci, Alessandra, Gianluigi Albano, Matteo Pollastrini, et al. "Supported Tris-Triazole Ligands for Batch and Continuous-Flow Copper-Catalyzed Huisgen 1,3-Dipolar Cycloaddition Reactions." Catalysts 10, no. 4 (2020): 434. http://dx.doi.org/10.3390/catal10040434.

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The lack of supported versions of the tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) ligand, suitable for flow-chemistry applications at scale, prompted us to develop a new route for the immobilization of such tris-triazole chelating units on highly cross-linked polystyrene resins. With this aim, the preparation of the known TBTA-type monomer 3 was optimized to develop a high-yield synthetic sequence, devoid of chromatographic purifications at any stage. Then, bead-type (P7) and monolithic (M7) functional resins were obtained by the easy and scalable suspension- or mold-copolymerizat

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Tripathi, Rama P., Amit Kumar Yadav, Arya Ajay, Surendra Singh Bisht, Vinita Chaturvedi, and Sudhir Kumar Sinha. "Application of Huisgen (3+2) cycloaddition reaction: Synthesis of 1-(2,3-dihydrobenzofuran-2-yl-methyl [1,2,3]-triazoles and their antitubercular evaluations." European Journal of Medicinal Chemistry 45, no. 1 (2010): 142–48. http://dx.doi.org/10.1016/j.ejmech.2009.09.036.

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35

Ting, S. R. Simon, Anthony M. Granville, Damien Quémener, Thomas P. Davis, Martina H. Stenzel, and Christopher Barner-Kowollik. "RAFT Chemistry and Huisgen 1,3-Dipolar Cycloaddition: A Route to Block Copolymers of Vinyl Acetate and 6-O-Methacryloyl Mannose?" Australian Journal of Chemistry 60, no. 6 (2007): 405. http://dx.doi.org/10.1071/ch07089.

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The present communication explores a novel avenue to glycopolymer-block-poly(vinyl acetate) polymers by a combination of reversible addition fragmentation chain transfer (RAFT) chemistry and Huisgen 1,3-dipolar cycloaddition (i.e., so-called ‘click’ chemistry) under mild reaction conditions. Such block copolymers are—because of the strongly disparate reactivity of the two monomers—otherwise not obtainable. Poly(vinyl acetate) that has an azide end group (Mn 6800 g mol–1, PDI 1.15) was treated with poly(6-O-methacryloyl mannose) (Mn 7600 g mol–1, PDI 1.11) in the presence of 1,8-diaza[5,4,0]bic

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Yamasaki, Shota, Yuri Kamon, Linlin Xu, and Akihito Hashidzume. "Synthesis of Dense 1,2,3-Triazole Polymers Soluble in Common Organic Solvents." Polymers 13, no. 10 (2021): 1627. http://dx.doi.org/10.3390/polym13101627.

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Aiming at synthesis of dense 1,2,3-triazole polymers soluble in common organic solvents, a new 3-azido-1-propyne derivative, i.e., t-butyl 4-azido-5-hexynoate (tBuAH), was synthesized and polymerized by copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) and Huisgen cycloaddition (HC). CuAAC polymerization produced poly(tBuAH) composed of 1,4-disubstituted 1,2,3-triazole units (1,4-units), whereas HC polymerization gave poly(tBuAH) composed of 1,4- and 1,5-disubstituted 1,2,3-triazole units (1,4- and 1,5-units). In HC polymerization, the fraction of 1,4-unit (f1,4) decreased with the permit

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Zhang, Yagang, and Steven C. Zimmerman. "Azobenzene dye-coupled quadruply hydrogen-bonding modules as colorimetric indicators for supramolecular interactions." Beilstein Journal of Organic Chemistry 8 (April 2, 2012): 486–95. http://dx.doi.org/10.3762/bjoc.8.55.

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The facile coupling of azobenzene dyes to the quadruply hydrogen-bonding modules 2,7-diamido-1,8-naphthyridine (DAN) and 7-deazaguanine urea (DeUG) is described. The coupling of azobenzene dye 2 to mono-amido DAN units 4, 7, and 9 was effected by classic 4-(dimethylamino)pyridine (DMAP)-catalyzed peptide synthesis with N-(3-dimethylaminopropyl)-N’-ethyl carbodiimide hydrochloride (EDC) as activating agent, affording the respective amide products 5, 8, and 10 in 60–71% yield. The amide linkage was formed through either the aliphatic or aromatic ester group of 2, allowing both the flexibility an

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Dabiri, Minoo, Siyavash Kazemi Movahed, and David Ian MaGee. "One-pot synthesis of 2,4,5-triaryl-1H-imidazoles linked 1,4-disubstituted 1,2,3-triazoles based on a merging multicomponent condensation with Huisgen 1,3-dipolar cycloaddition in ionic liquid." Research on Chemical Intermediates 41, no. 6 (2013): 3335–47. http://dx.doi.org/10.1007/s11164-013-1436-1.

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39

Matulis, Vitaly E., Ekaterina G. Ragoyja, Alexander V. Zuraev, Yuri V. Grigoriev, and Oleg A. Ivashkevich. "Theoretical and infrared spectroscopy study of the structure of copper(II) poly-5-vinyltetrazolate and the products of its thermolysis." Journal of the Belarusian State University. Chemistry, no. 1 (March 5, 2020): 19–31. http://dx.doi.org/10.33581/2520-257x-2020-1-19-31.

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The structure of copper(II) poly-5-vinyltetrazolate and the products of its thermolysis has been studied by means of density functional theory and infrared spectroscopy. Copper(II) poly-5-vinyltetrazolate has been obtained and subsequently subjected to thermolysis. Infrared spectra of copper(II) poly-5-vinyltetrazolate and the products of its thermolysis have been recorded. The possible ways of coordination of copper(II) ions with tetrazole-containing ligands were established by analyzing the calculated molecular electrostatic potential distribution and comparing the calculated IR-spectra of t

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Özdemir, Zülal, Michaela Rybková, Martin Vlk, David Šaman, Lucie Rárová, and Zdeněk Wimmer. "Synthesis and Pharmacological Effects of Diosgenin–Betulinic Acid Conjugates." Molecules 25, no. 15 (2020): 3546. http://dx.doi.org/10.3390/molecules25153546.

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The target diosgenin–betulinic acid conjugates are reported to investigate their ability to enhance and modify the pharmacological effects of their components. The detailed synthetic procedure that includes copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition (click reaction), and palladium-catalyzed debenzylation by hydrogenolysis is described together with the results of cytotoxicity screening tests. Palladium-catalyzed debenzylation reaction of benzyl ester intermediates was the key step in this synthetic procedure due to the simultaneous presence of a 1,4-disubstituted 1,2,3-triazole ring

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Zaki, Mohamed, Mohammed Loubidi, Tuğçe Bilgiç, et al. "Design, Synthesis, and Biological Evaluation of Novel Tomentosin Derivatives in NMDA-Induced Excitotoxicity." Pharmaceuticals 15, no. 4 (2022): 421. http://dx.doi.org/10.3390/ph15040421.

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N-methyl-D-aspartate (NMDA) receptor stimulation may lead to excitotoxicity, which triggers neuronal death in brain disorders. In addition to current clinical therapeutic approaches, treatment strategies by phytochemicals or their derivatives are under investigation for neurodegenerative diseases. In the present study, novel amino and 1,2,3-triazole derivatives of tomentosin were prepared and tested for their protective and anti-apoptotic effects in NMDA-induced excitotoxicity. Amino-tomentosin derivatives were generated through a diastereoselective conjugate addition of several secondary amin

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Maroto, Alicia, Ricard Boqué, Dany Jeanne Dit Fouque, and Antony Memboeuf. "Energy-Resolved Mass Spectrometry and Mid-Infrared Spectroscopy for Purity Assessment of a Synthetic Peptide Cyclised by Intramolecular Huisgen Click Chemistry." Methods and Protocols 7, no. 6 (2024): 97. https://doi.org/10.3390/mps7060097.

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Cyclic peptides have higher stability and better properties as therapeutic agents than their linear peptide analogues. Consequently, intramolecular click chemistry is becoming an increasingly popular method for the synthesis of cyclic peptides from their isomeric linear peptides. However, assessing the purity of these cyclic peptides by mass spectrometry is a significant challenge, as the linear and cyclic peptides have identical masses. In this paper, we have evaluated the analytical capabilities of energy-resolved mass spectrometry (ER MS) and mid-infrared microscopy (IR) to address this cha

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Prasch, Jürgen, Eva Bernhart, Helga Reicher, et al. "Myeloperoxidase-Derived 2-Chlorohexadecanal Is Generated in Mouse Heart during Endotoxemia and Induces Modification of Distinct Cardiomyocyte Protein Subsets In Vitro." International Journal of Molecular Sciences 21, no. 23 (2020): 9235. http://dx.doi.org/10.3390/ijms21239235.

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Sepsis is a major cause of mortality in critically ill patients and associated with cardiac dysfunction, a complication linked to immunological and metabolic aberrations. Cardiac neutrophil infiltration and subsequent release of myeloperoxidase (MPO) leads to the formation of the oxidant hypochlorous acid (HOCl) that is able to chemically modify plasmalogens (ether-phospholipids) abundantly present in the heart. This reaction gives rise to the formation of reactive lipid species including aldehydes and chlorinated fatty acids. During the present study, we tested whether endotoxemia increases M

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Kashina, Anna V., Tamara K. Meleshko, Natalia N. Bogorad, Viktor K. Lavrentyev та Alexander V. Yakimansky. "Molecular Brushes with a Polyimide Backbone and Poly(ε-Caprolactone) Side Chains by the Combination of ATRP, ROP, and CuAAC". Polymers 13, № 19 (2021): 3312. http://dx.doi.org/10.3390/polym13193312.

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An approach to the synthesis of the novel molecular brushes with a polyimide (PI) backbone and poly(ε-caprolactone) (PCL) side chains was developed. To obtain such copolymers, a combination of various synthesis methods was used, including polycondensation, atom transfer radical polymerization (ATRP), ring opening polymerization (ROP), and Cu (I)-catalyzed azide-alkyne Huisgen cycloaddition (CuAAC). ATRP of 2-hydroxyethyl methacrylate (HEMA) on PI macroinitiator followed by ROP of ε-caprolactone (CL) provided a “brush on brush” structure PI-g-(PHEMA-g-PCL). For the synthesis of PI-g-PCL two syn

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Nguyen, Duy Trinh, Nguyen Phu Thuong Nhan, Tran Thien Hien, Nguyen Dai Hai, Dai Viet N. Vo, and Long Giang Bach. "A Simple Approach for Immobilization of Fe-Core/Au-Shell Magnetic Nanoparticles on Multi-Walled Carbon Nanotubes via Cu(I) Huisgen Cycloaddition: Preparation and Characterization." Solid State Phenomena 279 (August 2018): 187–91. http://dx.doi.org/10.4028/www.scientific.net/ssp.279.187.

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In this report, we demonstrated a novel efficient a simple strategy route for the preparation of smart hybrid Fe-core/Au-shell magnetic onto multi-walled carbon nanotubes (CNT) sidewalls via Cu (I)-catalyzed 1, 3-dipolar cycloaddition (“click” coupling). The fabrication of gold-coated iron nanoparticles (Fe@AuNPs) is initially achieved by employing a two-step reverse micelle process. A new azide terminated ligand was first synthesized to change Fe@AuNPs by ligand exchange reaction. The Fe@Au NPs decorated MWNTs (MWNTs-Fe@Au) nanohybrids were synthesized by the reaction of an azide-containing F

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Sharma, Richa, Lalit Yadav, Ali Adnan Nasim, et al. "Chemo-/Regio-Selective Synthesis of Novel Functionalized Spiro[pyrrolidine-2,3′-oxindoles] under Microwave Irradiation and Their Anticancer Activity." Molecules 28, no. 18 (2023): 6503. http://dx.doi.org/10.3390/molecules28186503.

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A novel series of nitrostyrene-based spirooxindoles were synthesized via the reaction of substituted isatins 1a–b, a number of α-amino acids 2a–e and (E)-2-aryl-1-nitroethenes 3a–e in a chemo/regio-selective manner using [3+2] cycloaddition (Huisgen) reaction under microwave irradiation conditions. The structure elucidation of all the synthesized spirooxindoles were done using 1H and 13C NMR and HRMS spectral analysis. The single crystal X-ray crystallographic study of compound 4l was used to assign the stereochemical arrangements of the groups around the pyrrolidine ring in spiro[pyrrolidine-

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Silva, Bianca N. M., Policarpo A. Sales Junior, Alvaro J. Romanha, et al. "Synthesis of New Thiosemicarbazones and Semicarbazones Containing the 1,2,3-1H-triazole-isatin Scaffold: Trypanocidal, Cytotoxicity, Electrochemical Assays, and Molecular Docking." Medicinal Chemistry 15, no. 3 (2019): 240–56. http://dx.doi.org/10.2174/1573406414666180912120502.

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Background: Chagas disease, also known as American trypanosomiasis, is classified as one of the 17 most important neglected diseases by the World Health Organization. The only drugs with proven efficacy against Chagas disease are benznidazole and nifurtimox, however both show adverse effects, poor clinical efficacy, and development of resistance. For these reasons, the search for new effective chemical entities is a challenge to research groups and the pharmaceutical industry. Objective: Synthesis and evaluation of antitrypanosomal activities of a series of thiosemicarbazones and semicarbazone

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Gupta, Manjulla, Monika Gupta, Satya Paul, Rajni Kant, and Vivek K. Gupta. "One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles via Huisgen 1,3-dipolar cycloaddition catalysed by SiO2–Cu(I) oxide and single crystal X-ray analysis of 1-benzyl-4-phenyl-1H-1,2,3-triazole." Monatshefte für Chemie - Chemical Monthly 146, no. 1 (2014): 143–48. http://dx.doi.org/10.1007/s00706-014-1285-7.

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Gupta, Manjulla, Monika Gupta, Satya Paul, Rajni Kant, and Vivek K. Gupta. "ChemInform Abstract: One-Pot Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Huisgen 1,3-Dipolar Cycloaddition Catalyzed by SiO2-Cu(I) Oxide and Single Crystal X-Ray Analysis of 1-Benzyl-4-phenyl-1H-1,2,3-triazole." ChemInform 46, no. 21 (2015): no. http://dx.doi.org/10.1002/chin.201521161.

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MURAOKA, O., B. Z. ZHENG, K. OKUMURA, E. TABATA, G. TANABE, and M. KUBO. "ChemInform Abstract: Tandem Beckmann and Huisgen-White Rearrangement of the 9-Azabicyclo(3. 3.1)nonan-3-one System. Part 2. The Second Mode of the Rearrangement Leading to 6-(Prop-1-enyl)piperidin-2-ylacetic Acid, a Versatile Intermediate for the Synthese." ChemInform 28, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.199724229.

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