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Journal articles on the topic 'Microwave-assisted click reaction'

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Author: Grafiati

Published: 10 March 2023

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1

Munteanu, Maricica, SooWhan Choi, and Helmut Ritter. "Cyclodextrin Methacrylate via Microwave-Assisted Click Reaction." Macromolecules 41, no. 24 (December 23, 2008): 9619–23. http://dx.doi.org/10.1021/ma8018975.

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2

Yamamura, Hatsuo, Kana Isshiki, Yusuke Fujita, Hisato Kato, Takashi Katsu, Kazufumi Masuda, Kayo Osawa, and Atsushi Miyagawa. "Gramicidin S-inspired antimicrobial cyclodextrin to disrupt gram-negative and gram-positive bacterial membranes." MedChemComm 10, no. 8 (2019): 1432–37. http://dx.doi.org/10.1039/c9md00229d.

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3

Halwale, Amool, and B. Yadagiri. "Microwave Assisted Synthesis of Benzoxazole-Triazole Hybrid Derivatives as Antimicrobial Agents." Asian Journal of Chemistry 34, no. 4 (2022): 1015–20. http://dx.doi.org/10.14233/ajchem.2022.23546.

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A series of new 1,3-benzoxazole based 1,2,3-triazoles compounds were synthesized using click reaction under conventional and microwave irradiation methods. The microwave irradiation method gave higher yields, shorter reaction time as compared to conventional method using green solvents, eco-friendly reaction conditions. All the targeted compounds were characterized by IR, 1H, 13C NMR and mass spectral analysis. Furthermore, the titled compounds were screened for their in vitro antimicrobial activity against bacterial strains such as Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae and Escherichia coli as well as fungi such as Aspergillus niger, Aspergillus flavus and Fusarium oxysporum. Most of the compounds displayed good to excellent antimicrobial activity in comparison to standard drugs.

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4

Dharavath, Ravinder, Nalaparaju Nagaraju, M. Ram Reddy, D. Ashok, M. Sarasija, M. Vijjulatha, Vani T, K. Jyothi, and G. Prashanthi. "Microwave-assisted synthesis, biological evaluation and molecular docking studies of new coumarin-based 1,2,3-triazoles." RSC Advances 10, no. 20 (2020): 11615–23. http://dx.doi.org/10.1039/d0ra01052a.

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Coumarin-based 1,4-disubstituted 1,2,3-triazole derivatives were synthesized using a highly efficient, eco-friendly protocol via a copper(i)-catalyzed click reaction between various substituted arylazides and terminal alkynes.

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5

Chavez-Acevedo, Lizbeth, and Luis D. Miranda. "Synthesis of novel tryptamine-based macrocycles using an Ugi 4-CR/microwave assisted click-cycloaddition reaction protocol." Organic & Biomolecular Chemistry 13, no. 15 (2015): 4408–12. http://dx.doi.org/10.1039/c5ob00067j.

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6

Rijkers, Dirk T. S., G. Wilma van Esse, Remco Merkx, Arwin J. Brouwer, Hans J. F. Jacobs, Roland J. Pieters, and Rob M. J. Liskamp. "Efficient microwave-assisted synthesis of multivalent dendrimeric peptides using cycloaddition reaction (click) chemistry." Chemical Communications, no. 36 (2005): 4581. http://dx.doi.org/10.1039/b507975f.

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7

Cintas, Pedro, Katia Martina, Bruna Robaldo, Davide Garella, Luisa Boffa, and Giancarlo Cravotto. "Improved Protocols for Microwave-Assisted Cu(I)-Catalyzed Huisgen 1,3-Dipolar Cycloadditions." Collection of Czechoslovak Chemical Communications 72, no. 8 (2007): 1014–24. http://dx.doi.org/10.1135/cccc20071014.

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The Huisgen 1,3-dipolar cycloaddition of azides and acetylenes catalyzed by Cu(I) salts, leading to 1,2,3-triazoles, is one of the most versatile "click reactions". We have developed a series of optimized protocols and new applications of this reaction starting from several substrates, comparing heterogeneous vs homogeneous catalysis, conventional heating vs microwave irradiation or simultaneous microwave/ultrasound irradiation. Both non-conventional techniques strongly promoted the cycloaddition (bromide → azide → triazole), that could be conveniently performed in a one-pot procedure. This was feasible even with such bulky molecules as functionalized β-cyclodextrins (β-CD), starting from 61-O-tosyl-β-CD or from heptakis[6-O-(tert-butyldimethylsilyl)]-21-O-propargyl-β-CD. "Greener" heterogeneous catalysis with charcoal-supported Cu(II) or Cu(I) (prepared under ultrasound) was advantageously employed.

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8

Garska, Bernd, Monir Tabatabai, and Helmut Ritter. "Calix[4]arene-click-cyclodextrin and supramolecular structures with watersoluble NIPAAM-copolymers bearing adamantyl units: “Rings on ring on chain”." Beilstein Journal of Organic Chemistry 6 (August 5, 2010): 784–88. http://dx.doi.org/10.3762/bjoc.6.83.

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We describe the calixarene-cyclodextrin-coupling via click reaction starting from 5,11,17,23-tetra-tert-butyl-25,27-dipropargylether-26,28-hydroxy-calix[4]arene (calix[4]arene-dipropargylether) (2) onto 6I-azido-6I-deoxycyclomaltoheptaose (3) under microwave assisted conditions. The coupling was proven by MALDI-TOF mass spectrometry, 1H NMR and IR-spectroscopy. The pH dependent supramolecular complex formation with poly(NIPAAM) bearing attached adamantyl units was investigated by dynamic light scattering (DLS) and turbidity measurements.

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9

Yan, Lesan, Jianxun Ding, Ruogu Qi, Lixin Yang, Xiuli Hu, Yubin Huang, and Xiabin Jing. "Versatile synthesis of functional biodegradable polymers by ring-opening polymerization and microwave-assisted click reaction." Journal of Controlled Release 152 (November 2011): e249-e250. http://dx.doi.org/10.1016/j.jconrel.2011.09.042.

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10

Librando, Ivy L., Abdallah G. Mahmoud, Sónia A. C. Carabineiro, M. Fátima C. Guedes da Silva, Carlos F. G. C. Geraldes, and Armando J. L. Pombeiro. "Synthesis of a Novel Series of Cu(I) Complexes Bearing Alkylated 1,3,5-Triaza-7-phosphaadamantane as Homogeneous and Carbon-Supported Catalysts for the Synthesis of 1- and 2-Substituted-1,2,3-triazoles." Nanomaterials 11, no. 10 (October 13, 2021): 2702. http://dx.doi.org/10.3390/nano11102702.

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The N-alkylation of 1,3,5-triaza-7-phosphaadamantane (PTA) with ortho-, meta- and para-substituted nitrobenzyl bromide under mild conditions afforded three hydrophilic PTA ammonium salts, which were used to obtain a new set of seven water-soluble copper(I) complexes. The new compounds were fully characterized and their catalytic activity was investigated for the low power microwave assisted one-pot azide–alkyne cycloaddition reaction in homogeneous aqueous medium to obtain disubstituted 1,2,3-triazoles. The most active catalysts were immobilized on activated carbon (AC), multi-walled carbon nanotubes (CNT), as well as surface functionalized AC and CNT, with the most efficient support being the CNT treated with nitric acid and NaOH. In the presence of the immobilized catalyst, several 1,4-disubstituted-1,2,3-triazoles were obtained from the reaction of terminal alkynes, organic halides and sodium azide in moderate yields up to 80%. Furthermore, the catalyzed reaction of terminal alkynes, formaldehyde and sodium azide afforded 2-hydroxymethyl-2H-1,2,3-triazoles in high yields up to 99%. The immobilized catalyst can be recovered and recycled through simple workup steps and reused up to five consecutive cycles without a marked loss in activity. The described catalytic systems proceed with a broad substrate scope, under microwave irradiation in aqueous medium and according to “click rules”.

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11

Librando, Ivy L., Abdallah G. Mahmoud, Sónia A. C. Carabineiro, M. Fátima C. Guedes da Silva, Carlos F. G. C. Geraldes, and Armando J. L. Pombeiro. "Synthesis of a Novel Series of Cu(I) Complexes Bearing Alkylated 1,3,5-Triaza-7-phosphaadamantane as Homogeneous and Carbon-Supported Catalysts for the Synthesis of 1- and 2-Substituted-1,2,3-triazoles." Nanomaterials 11, no. 10 (October 13, 2021): 2702. http://dx.doi.org/10.3390/nano11102702.

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The N-alkylation of 1,3,5-triaza-7-phosphaadamantane (PTA) with ortho-, meta- and para-substituted nitrobenzyl bromide under mild conditions afforded three hydrophilic PTA ammonium salts, which were used to obtain a new set of seven water-soluble copper(I) complexes. The new compounds were fully characterized and their catalytic activity was investigated for the low power microwave assisted one-pot azide–alkyne cycloaddition reaction in homogeneous aqueous medium to obtain disubstituted 1,2,3-triazoles. The most active catalysts were immobilized on activated carbon (AC), multi-walled carbon nanotubes (CNT), as well as surface functionalized AC and CNT, with the most efficient support being the CNT treated with nitric acid and NaOH. In the presence of the immobilized catalyst, several 1,4-disubstituted-1,2,3-triazoles were obtained from the reaction of terminal alkynes, organic halides and sodium azide in moderate yields up to 80%. Furthermore, the catalyzed reaction of terminal alkynes, formaldehyde and sodium azide afforded 2-hydroxymethyl-2H-1,2,3-triazoles in high yields up to 99%. The immobilized catalyst can be recovered and recycled through simple workup steps and reused up to five consecutive cycles without a marked loss in activity. The described catalytic systems proceed with a broad substrate scope, under microwave irradiation in aqueous medium and according to “click rules”.

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12

Appukkuttan, Prasad, Wim Dehaen, Valery V. Fokin, and Erik Van der Eycken. "A Microwave-Assisted Click Chemistry Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via a Copper(I)-Catalyzed Three-Component Reaction." Organic Letters 6, no. 23 (November 2004): 4223–25. http://dx.doi.org/10.1021/ol048341v.

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13

Chavez-Acevedo, Lizbeth, and Luis D. Miranda. "ChemInform Abstract: Synthesis of Novel Tryptamine-Based Macrocycles Using an Ugi 4-CR/Microwave Assisted Click-Cycloaddition Reaction Protocol." ChemInform 46, no. 32 (July 24, 2015): no. http://dx.doi.org/10.1002/chin.201532154.

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14

Li, Yan, Jun Wang, and Chengzhi Cai. "Rapid Grafting of Azido-Labeled Oligo(ethylene glycol)s onto an Alkynyl-Terminated Monolayer on Nonoxidized Silicon via Microwave-Assisted “Click” Reaction." Langmuir 27, no. 6 (March 15, 2011): 2437–45. http://dx.doi.org/10.1021/la104060j.

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15

Mahmoud, Abdallah G., M. Fátima C. Guedes da Silva, Jerzy Sokolnicki, Piotr Smoleński, and Armando J. L. Pombeiro. "Hydrosoluble Cu(i)-DAPTA complexes: synthesis, characterization, luminescence thermochromism and catalytic activity for microwave-assisted three-component azide–alkyne cycloaddition click reaction." Dalton Transactions 47, no. 21 (2018): 7290–99. http://dx.doi.org/10.1039/c8dt01232f.

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16

Bardts, Mareike, and Helmut Ritter. "Microwave Assisted Synthesis of Thiol Modified Polymethacrylic acid and Its Cross-Linking with Allyl Modified Polymethacrylic acid via Thiol-ene “Click” Reaction." Macromolecular Chemistry and Physics 211, no. 7 (January 28, 2010): 778–81. http://dx.doi.org/10.1002/macp.200900608.

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17

Haensch, Claudia, Tina Erdmenger, Martin W. M. Fijten, Stephanie Hoeppener, and Ulrich S. Schubert. "Fast Surface Modification by Microwave Assisted Click Reactions on Silicon Substrates." Langmuir 25, no. 14 (July 21, 2009): 8019–24. http://dx.doi.org/10.1021/la901140f.

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18

Sameut, Asmaâ, Sarah Yasmine Zanndouche, Chaimaa Boumaza, Chaima Dikes, and Borhane Eddine Cherif Ziani. "Chemical Synthesis and Hemi-Synthesis of Novel Benzimidazole Derivatives Using Microwave-Assisted Process: Chemical Characterization, Bioactivities and Molecular Docking." Chemistry Proceedings 3, no. 1 (November 14, 2020): 71. http://dx.doi.org/10.3390/ecsoc-24-08306.

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Benzimidazole derivatives represent a class of heterocyclic compounds that exhibit a wide range of pharmaceutical properties. The present study aimed to investigate the in-vitro antioxidant and antimicrobial activities of newly synthesized benzimidazole derivatives. Compound 1b (2-(1H-1,3-benzodiazol-2-yl) phenol) was synthesized by reacting o-phenylenediamine (OPA) with chemical salicylaldehyde, while compounds 2b (2-(2-[(1E)-2-phenylethenyl]-1H-1,3-benzodiazole) and 3b (2-[(1E)-2,6-dimethylhepta-1,5-dien-1-yl]-1H-1,3-benzodiazole) were obtained through a hemi-synthesis process of, respectively, the cinnamon (cinnamaldehyde, 90.54%) and lemongrass (cis-citral, 43.9%) essential oils previously characterized by GC/MS. Compounds 4b (2-phenyl-1H-benzimidazole) and 5b (5-(1H-benzimidazol-2-yl)benzene-1,2,3-triol) were synthesized with a click chemistry method by reacting the OPA with benzoic acid and gallic acid directly in ethanol under microwave irradiation (MW) at 400 MHz. The structure/purity of the synthesized compounds was clarified by spectroscopy, ATR-FTIR and NMR 1H. Compounds 1b–5b were screened for their antioxidant activity by using four complementary in-vitro assays: DPPH scavenging activity, ferric ion reducing power, β-carotene bleaching inhibition, and Thiobarbituric Acid Reactive Substance Assay (TBARS) formation inhibition. All the tested compounds showed antioxidant potential, with varying performance. Antimicrobial activity was investigated against American Type Culture Collection (ATCC) strains (three Gram- bacteria: Escherichia coli, Salmonella typhi, and Pseudomonas aeruginosa; one Gram+ bacteria: Staphylococcus aureus, and one yeast strain: Candida albicans) through the determination of the Minimum Inhibitory Concentration (MIC) and the Minimum Bactericidal Concentration (MBC) by using the microdilution method and rapid colorimetric test of p-iodonitrotetrazolium chloride (INT). Compound 5b exhibited the highest potential, especially against S. aureus (MIC = 0.156 mg·mL−1) followed by S. typhi and C. albicans (MIC = 0.3125 mg·mL−1) and then by E. coli and P. aeruginosa. Compound 1b also showed great potential against S. aureus and C. albicans (MIC ˂ 0.3125 mg·mL−1), followed by E. coli and S. typhi (MIC = 0.3125 mg·mL−1) and P. aeruginosa (MIC = 0.625 mg·mL−1). Further molecular docking was conducted using AutoDock Vina 1.1.2 software on S. aureus thymidylate kinase (TMK) protein to highlight the structure–activity relationship of the potent molecules.

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19

"Microwave-Assisted Click Reaction Using Copper(I) Iodide on Alumina." Synfacts 11, no. 12 (November 17, 2015): 1330. http://dx.doi.org/10.1055/s-0035-1560886.

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20

Appukkuttan, Prasad, Wim Dehaen, Valery V. Fokin, and Erik Van der Eycken. "A Microwave-Assisted Click Chemistry Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via a Copper(I)-Catalyzed Three-Component Reaction." ChemInform 36, no. 10 (March 8, 2005). http://dx.doi.org/10.1002/chin.200510134.

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21

Ribeiro, Rayssa, Mariana Alves Eloy, Carla Santana Francisco, Clara Lirian Javarini, Gabriela Miranda Ayusso, Victor Da Rocha Fonseca, Wanderson Romão, et al. "Flavonoid derivatives targeting BCR-ABL kinase: Semisynthesis, Molecular dynamic simulations and Enzymatic inhibition." Current Topics in Medicinal Chemistry 21 (July 5, 2021). http://dx.doi.org/10.2174/1568026621666210705170047.

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Background: Natural products have been universally approached in the research of novel trends useful to detail the essential paths of the life sciences and as a strategy for pharmacotherapeutics. Objective: This work focuses on further modification to the 6-hydroxy-flavanone building block aiming to obtain improved BCR-ABL kinase inhibitors. Methods: Ether derivatives were obtained from Williamson synthesis and triazole from Microwave-assisted click reaction. Chemical structures were finely characterized through IR, 1H and 13C NMR and HRMS. They were tested for their inhibitory activity against BCR-ABL kinase. Results: Two inhibitors bearing a triazole ring as a pharmacophoric bridge demonstrated the strongest kinase inhibition at IC50 value of 364 nM (compound 3j) and 275 nM (compound 3k). Conclusion: 6-hydroxy-flavanone skeleton can be considered as a promising core for BCR-ABL kinase inhibitors.

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