Multicomponent click synthesis of new 1,2,3-triazole derivatives of pyrimidine nucleobases: Promising acidic corrosion inhibitors for steel

Molecules

Volumn 18, Issue 12, 2013, Pages 15064-15079

  González Olvera, Rodrigo ^a   Espinoza Vázquez, Araceli ^a   Negrón Silva, Guillermo E ^a   Palomar Pardavé, Manuel E ^a   Romero Romo, Mario A ^a   Santillan, Rosa ^b  

^a UNIVERSIDAD AUTÓNOMA METROPOLITANA   (Mexico)

^b DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

1,2,3 triazoles; Acidic corrosion; Multicomponent reaction; Nucleobases; Steel

Indexed keywords

PYRIMIDINE; PYRIMIDINE DERIVATIVE; STEEL; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLICK CHEMISTRY; CORROSION; IMPEDANCE; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

CLICK CHEMISTRY; CORROSION; ELECTRIC IMPEDANCE; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRIMIDINES; STEEL; TRIAZOLES;

EID: 84890937911     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181215064     Document Type: Article

References (56)

1. Agalave, S.G.; Maujan, S.R.; Pore, V.S. Click chemistry: 1,2,3-triazoles as pharmacophores. Chem. Asian J. 2011, 6, 2696-2718.
2. Ganesh, A. Potential biological activity of 1,4-sustituted-1H-[1,2,3] triazoles. Int. J. Chem. Sci. 2013, 11, 573-578.
3. Rostovtsev, V.V.; Green, L.G.; Fokin, V.V.; Sharpless, K.B. A stepwise Hiusgen cycloaddition process: Copper(I)-catalyzed regioselective "Ligation" of azides and terminal alkynes. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
4. Tornøe, C.W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057-3064.
5. Bock, V.D.; Hiemstra, H.; van Maarseveen, J.H. CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 2006, 1, 51-68.
6. Meldal, M.; Tornøe, C.W. Cu-catalyzed azide-alkyne cycloaddition. Chem. Rev. 2008, 108, 2952-3015.
7. Hein, J.E.; Fokin, V.V. Copper-catalyzed azide-alkyne cycloaddition (cuaac) and beyond: New reactivity of copper(I) acetylides. Chem. Soc. Rev. 2010, 39, 1302-1315.
8. 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.
9. Lallana, E.; Riguera, R.; Fernandez-Mejia, E. Reliable and efficient procedures for the conjugation of biomolecules through Huisgen azide-alkyne cycloadditions. Angew. Chem. Int. Ed. 2011, 50, 8794-8804.
10. Pedersen, D.S.; Abell, A. 1,2,3-Triazoles in peptidomimetic chemistry. Eur. J. Org. Chem. 2011, 2399-2411.
11. Efthymiou, T.; Gong, W.; Desaulniers, J.-P. Chemical architecture and applications of nucleic acid derivatives containing 1,2,3-triazole funtionalities synthesized via click chemistry. Molecules 2012, 17, 12665-12703.
12. Chittepu, P.; Sirivolu, V.R.; Seela, F. Nucleosides and oligonucleotides containing 1,2,3-triazole residues with nucleobase tethers: Synthesis via azide-alkyne "click" reaction. Bioorg. Med. Chem. 2008, 16, 8427-8439.
13. Lolk, L.; Pøhlsgaard, J.; Jepsen, A.S.; Hansen, L.H.; Nielsen, H.; Steffansen, S.I.; Sparving, L.; Nielsen, A.B.; Vester, B.; Nielsen, P. A click chemistry approach to pleuromutilin conjugates with nucleosides or acyclic nucleoside derivatives and their binding to the bacterial ribosome. J. Med. Chem. 2008, 51, 4957-4967.
14. Ganesen, M.; Muraleedharan, K.M. Synthesis of β-Hydroxyphosphonate and 1,2-Dihydroxy Acyclic Nucleoside Analogs via 1,3-Dipolar Cycloaddition Strategy. Nucleos. Nucleot. Nucleic Acids 2010, 29, 91-96.
15. Trakossas, S.; Coutouli-Argyropoulou, E.; Hadjipavlou-Litina, D.J. Synthesis of modified triazole nucleosides possessing one or two base moieties via a click chemistry approach. Tetrahedron Lett. 2011, 52, 1673-1676.
16. Jørgensen, A.S.; Shaikh, K.I.; Enderlin, G.; Ivarsen, E.; Kumar, S.; Nielsen, P. The synthesis of double-headed nucleosides by the cuaac reaction and their effect in secondary nucleic acid structures. Org. Biomol. Chem. 2011, 9, 1381-1388.
17. Parmenopoulou, V.; Chatzileontiadou, D.S.M.; Manta, S.; Bougiatioti, S.; Maragozidis, P.; Gkaragkouni, D.-N.; Kaffesaki, E.; Kantsadi, A.L.; Skamnaki, V.T.; Zographos, S.E.; et al. Triazole pyrimidine nucleosides as inhibitors of ribonuclease A. Synthesis, Biochemical, and structural evaluation. Bioorg. Med. Chem. 2012, 20, 7184-7193.
18. Krim, J.; Taourirte, M.; Grunewald, C.; Krstic, I.; Engels, J.W. Microwave-assisted click chemistry for nucleoside functionalization: useful derivatives for analytical and biological applications. Synthesis 2013, 45, 396-405.
19. Elayadi, H.; Smietana, M.; Pannecouque, C.; Leyssen, P.; Neyts, J.; Vasseur, J.-J.; Lazrek, H.B. Straightforward synthesis of triazoloacyclonucleotide phosphonates as potential hcv inhibitors. Bioorg. Med. Chem. Lett. 2010, 20, 7365-7368.
20. Glowacka, I.E.; Balzarini, J.; Wróblewski, A.E. Design, Synthesis, Antiviral, and cytotoxic evaluation of novel phosphonylated 1,2,3-triazoles as acyclic nucleotide analogues. Nucleos. Nucleot. Nucleic Acids 2012, 31, 293-318.
21. Piotrowska, D.G.; Balzarini, J.; Glowacka, I.E. Design, Synthesis, Antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a 1,2,3-triazole linker. Eur. J. Med. Chem. 2012, 47, 501-509.
22. Diab, S.A.; De Schutter, C.; Muzard, M.; Plantier-Royon, R.; Pfund, E.; Lequeux, T. Fluorophosphonylated nucleoside derivatives as new series of thymidine phosphorylase multisubstrate inhibitors. J. Med. Chem. 2012, 55, 2758-2768.
23. Glowacka, I.E.; Balzarini, J.; Wróblewski, A.E. Synthesis and biological evaluation of novel 1,2,3-triazolonucleotides. Arch. Pharm. Chem. 2013, 346, 278-291.
24. Soltani Rad, M.N.; Asrari, Z.; Behrouz, S.; Hakimelahi, G.H.; Khalafi-Nezhad, A. "Click Synthesis" of 1H-1,2,3-Triazolyl-Based Oxiconazole (=(1Z)-1-(2,4-Dichlorophenyl)-2-(1Himidazol-1-yl)ethanone O-[(2,4-Dichlorophenyl)methyl] oxime) Analogs. Helv. Chim. Acta 2011, 94, 2194-2206.
25. Kramer, R.A.; Bleicher, K.H.; Wennemers, H. Design and synthesis of nucleoproline amino acids for the straightforward preparation of chiral and conformationally constrained nucleopeptides. Helv. Chim. Acta 2012, 95, 2621-2634.
26. Wang, P.; Leung, C.-H.; Ma, D.-L.; Lu, W.; Che, C.-M. Organoplatinum(II) complexes with nucleobases motifs as inhibitors of human topoisomerase II catalytic activity. Chem. Asian J. 2010, 5, 2271-2280.
27. Noel, O.; Xie, J. Synthesis of nucleo aminooxy acid derivatives. Synthesis 2013, 45, 134-140.
28. Lu, J.; Hu. J.; Song, Y.; Ju, Y. A new dual-responsive organogel based on uracil-appended glycyrrhetinic acid. Org. Lett. 2011, 13, 3372-3375.
29. Negrón-Silva, G.E.; González-Olvera, R.; Angeles-Beltrán, D.; Maldonado-Carmona, N.; Espinoza-Vázquez, A.; Plomar-Pardavé, M.E.; Romero-Romo, M.A.; Santillan, R. Synthesis of New 1,2,3-Triazole Derivatives of Uracil and Thymine with Potential Inhibitory Activity against Acidic Corrosion of Steels. Molecules 2013, 18, 4613-4627.
30. Tourabi, M.; Nohair, K.; Traisnel, M.; Jama, C.; Bentiss, F. Electrochemical and XPS studies of the corrosion inhibition of carbon steel in hydrochloric acid pickling solutions by 3,5-bis(2-thiehylmethyl)-4-amino-1,2,4- triazole. Corros. Sci. 2013, 75, 123-133.
31. Ouici, H.B.; Benali, O.; Harek, Y.; Larabi, L.; Hammouti, B.; Guendouzi, A. Inhibition of mild steel corrosion in 5% HCl solution by 5-(2-hydroxyphenyl)- 1,2,4-triazole-3-thione. Res. Chem. Intermed. 2013, 39, 2777-2793.
32. John, S.; Joseph, A. Electro analytical, surface morphological and theoretical studies on the corrosion inhibition behavior of different 1,2,4-triazole precursors on mild steel in 1M hydrochloric acid. Mater. Chem. Phys. 2012, 133, 1083-1091.
33. Ansari, K.R.; Yadav, D.K.; Ebenso, E.E.; Quraishi, M.A. Novel and effective pyridyl substituted 1,2,4-triazole as corrosion inhibitor for mild steel in acid solution. Int. J. Electrochem. Sci. 2012, 7, 4780-4799.
34. Mert, B.D.; Mert, M.E.; Kardas, G.; Yazici, B. Experimental and theoretical investigation of 3-amino-1,2,4-triazole-5-thiol as a corrosion inhibitor for carbon steel in HCl medium. Corros. Sci. 2011, 53, 4265-4272.
35. Zhang, T.; Cao, S.; Quan, H.; Huang, Z.; Xu, S. Synthesis and corrosion inhibition performance of alkyl triazole derivatives. Res. Chem. Intermed. 2013, doi: 10.1007/s11164-013-1381-z.
36. Deng, Q.; Ding, N.-N.; Wei, X.-L.; Cai, L.; He, X.-P.; Long, Y.-T.; Chen, G.-R.; Chen, K. Identification of diverse 1,2,3-triazole-connected benzyl glycoside-serine/threonine conjugates as potent corrosion inhibitors for mild steel in HCl. Corros. Sci. 2012, 64, 64-73.
37. Deng, Q.; Shi, H.-W.; Ding, N.-N.; Chen, B.-Q.; He, X.-P.; Liu, G.; Tang, Y.; Long, Y.-T.; Chen, G.-R. Novel triazolyl bis-amino acid derivatives readily synthesized via click chemistry as potential corrosion inhibitors for mild steel in HCl. Corros. Sci. 2012, 57, 220-227.
38. Zhang, H.-L.; He, X.-P.; Deng, Q.; Long, Y.-T.; Chen, G.-R.; Chen, K. Research on the structuresurface adsorptive activity relationships of triazolyl glycolipid derivatives for mild steel in HCl. Carbohydr. Res. 2012, 354, 32-39.
39. Malki Alaoui, L.; Hammouti, B.; Bellaouchou, A.; Benbachir, A.; Guenbour, A.; Kertit, S. Corrosion inhibition and adsorption properties of 3-amino-1,2,3-triazole on mild steel in H3PO4. Pharm. Chem. 2011, 3, 353-360.
40. Espinoza-Vázquez, A.; Negrón-Silva G.E.; Angeles-Beltrán, D.; Palomar-Pardavé, M.E.; Romero-Romo, M.A.; Herrera-Hernández, H. Electrochemical impedance evaluation of uracil and thymine pyrimidine derivatives and its nucleosides compounds as a non-toxic corrosion inhibitors of steels in 1M HCl. ECS Trans. 2011, 36, 217-228.
41. Lazrek, H.B.; Taourirte, M.; Oulih, T.; Kabbaj, Y.; Barascut, J.L.; Imbach, J.L.; Almasoudi, N.A.; Pfleiderer, W. Synthesis of 3′-deoxy-3' and 5′-deoxy-5′-[4-(purin-9-yl/pyrimidin-1-yl)methyl-1,2,3-triazol-1- yl]thymidine via 1,3-dipolar cycloaddition. Nucleo. Nucleot. 1997, 16, 1073-1077.
42. Lazrek, H.B.; Taourirte, M.; Oulih, T.; Barascut, J.L.; Imbach, J.L.; Pannecouque, C.; Witrouw, M.; de Clercq, E. Synthesis and anti-hiv activity of new modified 1,2,3-triazole acyclonucleosides. Nucleo. Nucleot. Nucleic Acids 2001, 20, 1949-1960.
43. Hakimelahi, G.H.; Gassanov, G.S.; Hsu, M.-H.; Hwu, J.R.; Hakimelahi, S. A novel approach towards studying non-genotoxic enediynes as potential anticancer therapeutics. Bioorg. Med. Chem. 2002, 10, 1321-1328.
44. Ubasawa, M.; Takashima, H.; Sekiya, K. A convenient one-pot synthesis of acyclonucleosides. Chem. Pharm. Bull. 1995, 43, 142-143.
45. Lindsell, W.E.; Murray, C.; Preston, P.N.; Woodman, T.A.J. Synthesis of 1,3-diynes in the purine, pyrimidine, 1,3,5-triazine and acridine series. Tetrahedron 2000, 56, 1233-1245.
46. Hamon, F.; Violeau, B.; Turpin, F.; Bellot, M.; Bouteiller, L.; Djedaini-Pilard, F.; Len, C. Potential supramolecular cyclodextrin dimers using nucleobase pairs. Synlett 2009, 2875-2879.
47. Appukkuttan, P.; Dehaen, W.; Fokin, V.V.; van der Eycken, E. A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(i)-catalyzed three-component reaction. Org. Lett. 2004, 6, 4223-4225.
48. Chandrasekhar, S.; Basu, D.; Rambabu, Ch. Three-component coupling of alkynes, Baylis-Hillman adducts and sodium azide: A new synthesis of substituted triazoles. Tetrahedron Lett. 2006, 47, 3059-3063.
49. Malnuit, V.; Duca, M.; Manout, A.; Bougrin, K.; Benhida, R. Tandem azide-alkyne 1,3-dipolar cycloaddition/electrophilic addition: A concise three-component route to 4,5-disubstituted triazolyl-nucleosides. Synlett 2009, 2123-2128.
50. Zhang, J.; Wu, J.; Shen, L.; Jin, G.; Cao, S. Novel synthesis of difluoromethyl-containing 1,4-disubstituted 1,2,3-triazoles via a click-multicomponent reaction and desulfanylation strategy. Adv. Synth. Catal. 2011, 353, 580-584.
51. Mendoza-Espinosa, D.; Negrón-Silva, G.E.; Lomas-Romero, L.; Gutiérrez-Carrillo, A.; Soto-Castro, D. Efficient multicomponent synthesis of mono-, bis-, and tris-1,2,3-triazoles supported by hydroxybenzene scaffolds. Synthesis 2013, 45, 2431-2437.
52. Creary, X.; Anderson, A.; Brophy, C.; Crowell, F.; Funk, Z. Method for assigning structure of 1,2,3-triazoles. J. Org. Chem. 2012, 77, 8756-8761.
53. Yan, Y.; Wang, X.; Zhang, Y.; Wang, P.; Zhang, J. Theoretical evaluation of inhibition performance of purine corrosion inhibitors. Mol. Simulat. 2013, 39, 1034-1041.
54. Cruz-Gonzalez, D.Y.; Negrón-Silva, G.; Angeles-Beltrán, D.; Palomar-Pardavé, M.; Romero-Romo, M.; Herrera-Hernández, H. Adenine and guanine derivative bases of purines and their corresponding nucleosides as corrosion inhibitors in 1M hydrochloric acid. ECS Trans. 2011, 36, 179-185.
55. Yan, Y.; Li, W.; Cai, L.; Hou, B. Electrochemical and quantum chemical study of purines as corrosion inhibitors for mild steel in 1M HCl solution. Electrochim. Acta 2008, 53, 5953-5960.
56. Elayadi, H.; Ali, M.A.; Mehdi, A.; Lazrek, H.B. Nanoscrystalline CuO: Synthesis and application as an efficient catalyst for the preparation of 1,2,3-triazole acyclic nucleosides via 1,3-dipolar cycloaddition. Catal. Commun. 2012, 26, 155-158.