One-pot tandem copper-catalyzed library synthesis of 1-thiazolyl-1,2,3- triazoles as anticancer agents

ACS Combinatorial Science

Volumn 13, Issue 1, 2011, Pages 72-78

  Li, Wen Tai ^a   Wu, Wan Hsun ^a   Tang, Chien Hsiang ^a   Tai, Ready ^a   Chen, Shui Tein ^a,b  

^a INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

1 thiazolyl 1,2,3 triazole; CuAAC reaction; Cytotoxic activity; One pot synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; COPPER; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; FLUORESCENCE; SCANNING ELECTRON MICROSCOPY; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CATALYSIS; COPPER; FLUORESCENCE; MICROSCOPY, ELECTRON, SCANNING; TRIAZOLES;

EID: 78651465356     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co1000234     Document Type: Article

References (33)

1. Akritopoulou-Zanze, I. Isocyanide-based multicomponent reactions in drug discovery Curr. Opin. Chem. Biol. 2008, 12, 324-331
2. Shaabani, A.; Maleki, A.; Mofakham, H.; Khavasi, H. R. Novel isocyanide-based three-component one-pot synthesis of cyanophenylamino-acetamide derivatives J. Comb. Chem. 2008, 10, 883-885
3. Janvier, P.; Sun, X.; Bienaymé, H.; Zhu, J. Ammonium chloride-promoted four-component synthesis of pyrrolo[3,4- b ]pyridin-5-one J. Am. Chem. Soc. 2002, 124, 2560-2567
4. Volonterio, A.; Zanda, M. Multicomponent, one-pot sequential synthesis of 1,3,5- and 1,3,5,5-substituted barbiturates J. Org. Chem. 2008, 73, 7486-7497
5. Maiti, S.; Biswas, S.; Jana, U. Iron(III)-catalyzed four-component coupling reaction of 1,3-dicarbonyl compounds, amines, aldehydes, and nitroalkanes: a simple and direct synthesis of functionalized pyrroles J. Org. Chem. 2010, 75, 1674-1683
6. Tu, S.-J.; Zhang, X.-H.; Han, Z.-G.; Cao, X.-D.; Wu, S.-S.; Yan, S.; Hao, W.-J.; Zhang, G.; Ma, N. Synthesis of isoxazolo[5,4- b ]pyridines by microwave-assisted multi-component reactions in water J. Comb. Chem. 2009, 11, 428-432
7. Yermolayev, S. A.; Gorobets, N. Y.; Desenko, S. M. Rapid three-step one-pot microwave-assisted synthesis of 2,5-dioxo-1,2,5,6,7,8-hexahydro-3- quinolinecarbonitrile library J. Comb. Chem. 2009, 11, 44-46
8. Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. Programmable one-pot oligosaccharide synthesis J. Am. Chem. Soc. 1999, 121, 734-753
9. Zhang, W.; Luo, Z.; Chen, C. H.-T.; Curran, D. B. Solution-phase preparation of a 560-compound library of individual pure mappicine analogues by fluorous mixture synthesis J. Am. Chem. Soc. 2002, 124, 10443-10450
10. Ghahremanzadeh, R.; Shakibaei, G. I.; Ahadi, S.; Bazgir, A. One-pot, pseudo four-component synthesis of a spiro[diindeno[1,2- b:2′,1′- e ]pyridine-11,3′-indoline]-trione library J. Comb. Chem. 2010, 12, 191-194
11. Zhang, Q.; Wang, D.; Wang, X.; Ding, K. (2-Pyridyl)acetone-promoted Cu-catalyzed O-arylation of phenols with aryl iodides, bromides, and chlorides J. Org. Chem. 2009, 74, 7187-7190
12. Amblard, F.; Cho, J. H.; Schinazi, R. F. Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry Chem. Rev. 2009, 109, 4207-4220
13. Meldal, M.; Torn-e, C. W. Cu-catalyzed azide-alkyne cycloaddition Chem. Rev. 2008, 108, 2952-3015
14. Bae, I.; Han, H.; Chang, S. Highly efficient one-pot synthesis of N -sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine J. Am. Chem. Soc. 2005, 127, 2038-2039
15. Ma, D.; Cai, Q. Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles Acc. Chem. Res. 2008, 41, 1450-1460
16. NAR reactions: direct amination of electron deficient aryl halides with sodium azide and the synthesis of arylthioethers under Cu(II)-ascorbate redox system Tetrahedron 2010, 66, 7642-7650
17. Amblard, F.; Cho, J. H.; Schinazi, R. F. Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry Chem. Rev. 2009, 109, 4207-4220
18. Dirks, A. J.; Cornelissen, J. L. M.; Nolte, R. J. M. Monitoring protein-polymer conjugation by a fluorogenic Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition Bioconjugate Chem. 2009, 20, 1129-1138
19. Meldal, M.; Torn-e, W. T. Cu-catalyzed azide-alkyne cycloaddition Chem. Rev. 2008, 108, 2952-3015
20. Cintas, P.; Barge, A.; Tagliapietra, S.; Boffa, L.; Cravotto, G. Alkyne-azide click reaction catalyzed by metallic copper under ultrasound Nat. Protoc. 2010, 5, 607-616
21. Orski, S. V.; Poloukhtine, A. A.; Arumugam, S.; Mao, L.; Popik, V. V.; Locklin, J. High density orthogonal surface immobilization via photoactivated copper-free click chemistry J. Am. Chem. Soc. 2010, 132, 11024-11026
22. Jakobsen, U.; Shelke, S. A.; Vogel, S.; Sigurdsson, S. T. Site-directed spin-labeling of nucleic acids by click chemistry: detection of abasic sites in duplex DNA by EPR spectroscopy J. Am. Chem. Soc. 2010, 132, 10424-10428
23. Ferreira, S. B.; Sodero, A. C. R.; Cardoso, M. F. C.; Lima, E. S.; Kaiser, C. R.; Silva, F. P.; Ferreira, V. F. Synthesis, biological activity, and molecular modeling studies of 1 H -1,2,3-triazole derivatives of carbohydrates as α-glucosidases inhibitors J. Med. Chem. 2010, 53, 2364-2375
24. Yuldasheva, K.; Dzhuraev, A. D.; Makhsumov, A. G.; Amanov, N. Antimicrobial activity of bis(1,2,3-triazole) derivatives Pharm. Chem. J. 1991, 25, 728-730
25. Cho, J. H.; Bernard, D. L.; Sidwell, R. W.; Kern, E. R.; Chu, C. K. Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS J. Med. Chem. 2006, 49, 1140-1148
26. Giffin, M. J.; Heaslet, H.; Brik, A.; Lin, Y.-C.; Cauvi, G.; Wong, C.-H.; McRee, D. E.; Elder, J. H.; Stout, C. D.; Torbett, B. E. A copper(I)-catalyzed 1,2,3-triazole azide-alkyne click compound is a potent inhibitor of a multidrug-resistant HIV-1 protease variant J. Med. Chem. 2008, 51, 6263-6270
27. Reck, F.; Zhou, F.; Girardot, M.; Kern, G.; Eyermann, C. J.; Hales, N. J.; Ramsay, R. R.; Gravestock, M. B. Identification of 4-substituted 1,2,3-triazoles as novel oxazolidinone antibacterial agents with reduced activity against monoamine oxidase A J. Med. Chem. 2005, 48, 499-506
28. Li, W.-T.; Hwang, D.-R.; Song, J.-S.; Chen, C.-P.; Chuu, J.-J.; Hu, C.-B.; Lin, C.-C.; Lin, H.-L.; Wang, H.-S.; Shen, C.-C.; Huang, C.-L.; Tseng, H.-Y.; Huang, C.-Y.; Chen, T.-W.; Lin, C.-H.; Chang, C.-M.; Chao, Y.-S.; Chen, C.-T. Synthesis and biological activities of 2-amino-1-arylidenamino imidazoles as orally active anticancer agents J. Med. Chem. 2010, 53, 2409-2417
29. Li, W.-T.; Hwang, D.-R.; Song, J.-S.; Chen, C.-P.; Chen, T.-W.; Lin, C.-H.; Chuu, J.-J.; Lien, T.-W.; Hsu, T.-A.; Huang, C.-L.; Tseng, H.-Y.; Lin, C.-C.; Lin, H.-L.; Chang, C.-M.; Chao, Y.-S.; Chen, C.-T. Synthesis and biological evaluation of 2-amino-1-thiazolyl imidazoles as orally active anticancer agents. Unpublished results.
30. Giovannini, R.; Petrini, M. Ruthenium tetroxide catalyzed oxidations of 3-alkyl-4-(2-furyl)-4-oxobutanenitriles: Synthesis of methyl 2-alkyl-3-cyanopropanoates Tetrahedron Lett. 1997, 38, 3781-3784
31. Dotsenko, V. V.; Krivokolysko, S. G.; Chernega, A. N.; Litvinovc, V. P. A new stereoselective synthesis of 2-amino-4,5-dihydrothiophene-3-carbonitrile derivatives Russ. Chem. Bul. 2007, 56, 1431-1436
32. Delbecq, F.; Cordonnier, G.; Pommery, N.; Barbrya, D.; He′nichart, J.-P. New heteroarylbenzenesulphonamides as matrix metalloproteinase inhibitors Bioorg. Med. Chem. Lett. 2004, 14, 1119-1121
33. There is a byproduct, 2-amino-4-(2-furyl)thiazole, generated in this step. This byproduct was contributed from the reduction of 2-azido-4-(2-furyl) thiazole.