Design, synthesis, and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs

Medicinal Chemistry Research

Volumn 23, Issue 3, 2014, Pages 1501-1511

  De Lourdes G Ferreira, Maria ^a   Pinheiro, Luiz C S ^a   Santos Filho, Osvaldo A ^a   Peçanha, Marta D S ^a   Sacramento, Carolina Q ^a   Machado, Viviane ^a   Ferreira, Vitor F ^b   Souza, Thiago Moreno L ^a   Boechat, Núbia ^a  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

^b FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

Author keywords

1,2,3 Triazole; Antiviral; Influenza A; Reverse transcriptase; Ribavirin

Indexed keywords

EID: 84893736370     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0762-6     Document Type: Article

References (59)

1. Aher NG, Pore VS, Mishra NN, Kumar A, Shukla PK, Sharma A, Bhat MK (2009) Synthesis and antifungal activity of 1,2,3-triazole containing fluconazole analogues. Bioorg Med Chem Lett 19(3):759-763
2. Amblard F, Cho JH, Schinazi RF (2009) Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry. Chem Rev 109(9):4207-4220
3. Ankati H, Biehl E (2009) Microwave-assisted benzyne-click chemistry: preparation of 1H-benzo[d][1,2,3]triazoles. Tetrahedron Lett 50:4677-4682
4. Boechat N, Ferreira MLG, Bastos MM, Camilo ALS, Wardell SMSV, Wardell JL, Tiekink ERT (2010) Crystal and molecular structures of two triazole derivatives: 4-cyclopropyl-4,5-dihydro-1H-1,2,3-triazole and methyl 1-benzyl-1H-1,2,3-triazole-4-carboxylate. J Chem Crystallogr 40(12):1137-1141
5. Boechat N, Ferreira VF, Ferreira SB, Ferreira MLG, Silva FC, Bastos MM, Costa MS, Lourenco MCS, Pinto AC, Krettli AU, Aguiar AC, Teixeira BM, Silva NV, Martins PRC, Bezerra FAFM, Camilo ALS, Silva GP, Costa CCP (2011a) Novel 1,2,3-triazole derivatives for use against Mycobacterium tuberculosis H37Rv (ATCC 27294) strainz. J Med Chem 54(17):5988-5999
6. Boechat N, Pinheiro LCS, Santos-Filho OA, Silva IC (2011b) Design and synthesis of new N-(5-trifluoromethyl)-1H-1,2,4-triazol-3-yl benzenesulfonamides as possible antimalarial prototypes. Molecules 16(9):8083-8097
7. Campbell-Verduyn LS, Mirfeizi L, Dierckx RA, Elsinga PH, Feringa BL (2009) Phosphoramidite accelerated copper(I)-catalyzed [3 + 2] cycloadditions of azides and alkynes. Chem Commun 16:2139-2141
8. Chrysina ED, Bokor E, Alexacou KM, Charavgi MD, Oikonomakos GN, Zographos SE, Leonidas DD, Oikonomakos NG, Laszlo S (2009) Amide-1,2,3-triazole bioisosterism: the glycogen phosphorylase case. Tetrahedron 20(6-8):733-740
9. Coghi P, Vaiana N, Pezzano MG, Rizzi L, Kaiser M, Brun R, Romeo S (2008) Parallel synthesis and antileishmanial activity of ether-linked phospholipids. Bioorg Med Chem Lett 18(16):4658-4660
10. Das K, Martinez SE, Bauman JD, Arnold E (2012) HIV-1 reverse transcriptase complex with DNA and nevirapine reveals non-nucleoside inhibition mechanism. Nat Struct Mol Biol 19(2):253-259
11. De Clercq E (2004) Antiviral drugs in current clinical use. J Clin Virol 30(2):115-133
12. Denizot F, Lang R (1986) Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Methods 89(2):271-277
13. Dias R, Azebedo WF Jr (2008) Molecular docking algorithms. Curr Drug Targets 9(12):1040-1047
14. El Akri K, Bougrin K, Balzarini J, Faraj A, Benhida R (2007) Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl- nucleosides. Bioorg Med Chem Lett 17(23):6656-6659
15. 7 catalyzed azide-alkyne 1,3-dipolar cycloaddition. ARKIVOC viii:76-89
16. Estermam H, Seebach D (1988) Diastereoselektive alkylierung von 3-aminobutansäure in der 2-stellung. Helv Chim Acta 71(7):1824-1839
17. Fernandez-Larsson R, Patterson JL (1990) Ribavirin is an inhibitor of human immunodeficiency virus reverse transcriptase. Mol Pharmacol 38(6):766-770
18. Ferreira SB, Costa MS, Boechat N, Bezerra SRJ, Genestra MS, Canto-Cavalheiro MM, Kover WB, Ferreira VF (2007) Synthesis and evaluation of new difluoromethyl azoles as antileishmanial agents. Eur J Med Chem 42(11-12):1388-1395
19. Ferreira ML, Souza MVN, Wardell SMSV, Wardell JL, Vasconcelos TRA, Ferreira VF, Lourenço MCS (2010a) Synthesis and antitubercular evaluation of new bis-1,2,3-triazoles derived from d-mannitol. J Carbohydr Chem 29(6):265-274
20. Ferreira SB, Sodero ACR, Cardoso MFC, Lima ES, Kaiser CR, Silva FP Jr, Ferreira VF (2010b) Synthesis, biological activity, and molecular modeling studies of 1H-1,2,3-triazole derivatives of carbohydrates as α-glucosidases inhibitors. J Med Chem 53(6):2364-2375
21. Hou S, Liu W, Ji D, Zhao Z (2011) Efficient synthesis of triazole moiety-containing nucleotide analogs and their inhibitory effects on a malic enzyme. Bioorg Med Chem Lett 21(6):1667-1669
22. Huang Q, Zheng M, Yang S, Kuang C, Yu C, Yang Q (2011) Structure-activity relationship and enzyme kinetic studies on 4-aryl-1H-1,2,3-triazoles as indoleamine 2,3-dioxygenase (IDO) inhibitors. Eur J Med Chem 46(11):5680-5687
23. Jordão AK, Afonso PP, Ferreira VF, Souza MCBV, Almeida MCB, Beltrame CO, Paiva DP, Wardell SMSV, Wardell JL, Tiekink ERT, Damaso CR, Cunha AC (2009) Antiviral evaluation of N-amino-1,2,3-triazoles against Cantagalo virus replication in cell culture. Eur J Med Chem 44(9):3777-3783
24. Jordão AK, Ferreira VF, Souza TML, Faria GGS, Machado V, Abrantes JL, Souza MCBV, Cunha AC (2011a) Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives. Bioorg Med Chem 19(6):1860-1865
25. Jordão AK, Sathler PC, Ferreira VF, Campos VR, Souza MCBV, Castro HC, Lannes A, Lourenco A, Rodrigues CR, Bello ML, Lourenco MCS, Carvalho GSL, Almeida MCB, Cunha AC (2011b) Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides. Bioorg Med Chem 19(18):5605-5611
26. Júnior ENS, Moura MABF, Pinto AV, Pinto MCFR, Souza MCBV, Araújo AJ (2009) Cytotoxic, trypanocidal activities and physicochemical parameters of nor-β-lapachone-based 1,2,3-triazoles. J Braz Chem Soc 20(4):635-643
27. Kacprzak K (2005) Efficient one-pot synthesis of 1,2,3-triazoles from benzyl and alkyl halides. Synlett 6:943-946
28. Kharb R, Yar MS, Sharma PC (2011) Recent advances and future perspectives of triazole analogs as promising antiviral agents. Mini Rev Med Chem 11(1):84-96
29. Kim WY, Young Suh G, Huh JW, Kim SH, Kim MJ, Kim YS, Kim HR, Ryu YJ, Han MS, Ko YG, Chon GR, Lee KH, Choi SH, Hong SB, Korean Society of Critical Care Medicine H1N1 Collaborative (2011) Triple-combination antiviral drug for pandemic H1N1 influenza virus infection in critically ill patients on mechanical ventilation. Antimicrob Agents Chemother 55(12):5703-5709
30. Kirschberg TA, Balakrishnan M, Huang W, Hluhanich R, Kutty N, Liclican AC, McColl DJ, Squires NH, Lansdon EB (2008) Triazole derivatives as non-nucleoside inhibitors of HIV-1 reverse transcriptase-structure-activity relationships and crystallographic analysis. Bioorg Med Chem Lett 18(3):1131-1134
31. Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed Engl 40(11):2004-2021
32. Kornev AB, Peregudov AS, Martynenko VM, Balzarini J, Hoorelbeke B, Troshin PA (2011) Synthesis and antiviral activity of highly water-soluble polycarboxylic derivatives of [70]fullerene. Chem Commun 47(29):8298-8300
33. Krilov LR (2011) Respiratory syncytial virus disease: update on treatment and prevention. Expert Rev Anti Infect Ther 9(1):27-32
34. Kuo YC, Chen CC, Tsai WJ, Ho YH (2001) Regulation of herpes simplex virus type 1 replication in Vero cells by Psychotria serpens: relationship to gene expression, DNA replication, and protein synthesis. Antiviral Res 51(2):95-109
35. Lu Y, Gervay-Hague J (2007) Synthesis of C-4 and C-7 triazole analogs of zanamivir as multivalent sialic acid containing scaffolds. Carbohydr Res 342(12-13):1636-1650
36. Magden J, Kääriäinen L, Ahola T (2005) Inhibitors of virus replication: recent developments and prospects. Appl Microbiol Biotechnol 66(6):612-621
37. Markland W, McQuaid TJ, Jain J, Kwong AD (2000) Broad-spectrum antiviral activity of the IMP dehydrogenase inhibitor VX-497: a comparison with ribavirin and demonstration of antiviral additivity with alpha interferon. Antimicrob Agents Chemother 44(4):859-866
38. Matta AD, Bernardino AMR, Romeiro GA, Oliveira MRP, Souza MCBV, Ferreira VF (1996) Nucleosides having quinolones derivatives as nitrogenated base: regiospecific and stereospecific ribosylation of 3-carbethoxy-1,4-dihydro-4- oxoquinoline. Nucleosides Nucleotides 15(4):889-898
39. Matta AD, Santos CVB, Pereira HS, Frugulhetti ICPP, Oliveira MRP, Souza MCBV, Moussatché N, Ferreira VF (1999) Synthesis of novel nucleosides of 4-oxoquinoline-3-carboxylic acid analogues. Heteroatom Chem 10(3):197-202
40. Molegro Virtual Docker/4.0 Molegro ApS: Aarhus, Denmark, 2009
41. Pagliai F, Pirali T, Gross ED, Brisco RD, Tron GC, Sorba G, Genazzani AA (2006) Rapid synthesis of triazole-modified resveratrol analogues via click chemistry. J Med Chem 49(2):467-470
42. Pasman L (2012) The complication of coinfection. Yale J Biol Med 85(1):127-132
43. Pérez-Castro I, Caamano O, Fernández F, García MD, López C, De Clercq E (2007) Synthesis of 4-substituted-1,2,3-triazole carbanucleoside analogues of ribavirin via click chemistry. Org Biomol Chem 5:3805-3813
44. Piotrowska DG, Balzarini J, Glowacka IE (2012) Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a 1,2,3-triazole linker. Eur J Med Chem 47:501-509
45. Rocha DR, Santos WC, Lima ES, Ferreira VF (2012) Synthesis of 1,2,3-triazole glycoconjugates as inhibitors of α-glucosidases. Carbohydr Res 350:14-19
46. Rosa M, Kim HW, Gunic E, Jenket C, Boyle U, Koh Y, Korboukh I, Allan M, Zhang W, Chen H, Xu W, Nilar S, Yao N, Hamatake R, Lang SA, Hong Z, Zhang Z, Girardet J-L (2006) Tri-substituted triazoles as potent non-nucleoside inhibitors of the HIV-1 reverse transcriptase. Bioorg Med Chem Lett 16(17):4444-4449
47. Saladino R, Barontini M, Crucianelli M, Nencioni L, Sgarbanti R, Palamara AT (2010) Current advances in anti-influenza therapy. Curr Med Chem 17(20):2101-2140
48. Sarrazin C, Hézode C, Zeuzem S, Pawlotsky JM (2012) Antiviral strategies in hepatitis C virus infection. J Hepatol 56(1):S88-S100
49. Shawali AS (2010) Tandem in situ generation and 1,5-electrocyclization of N-hetaryl nitrilimines. A facile methodology for synthesis of annulated 1,2,4-triazoles and their acyclo C-nucleosides. ARKIVOC i:33-97
50. Silva EN Jr, Menna-Barreto RFS, Pinto MCFR, Silva RFS, Teixeira DV, Souza MCBV, Simone CA, Castro SL, Ferreira VF, Pinto AV (2008) Naphthoquinoidal [1,2,3]-triazole, a new structural moiety active against Trypanosoma cruzi. Eur J Med Chem 43(8):1774-1780
51. Silva FC, Souza MCBV, Frugulhetti ICPP, Castro HC, Souza SLO, Souza TML, Rodriques DQ, Souza AMT, Abreu PA, Passamani F, Rodrigues CR, Ferreira VF (2009) Synthesis, HIV-RT inhibitory activity and SAR of 1-benzyl-1H-1,2,3-triazole derivatives of carbohydrates. Eur J Med Chem 44(1):373-383
52. Souza TM, Rodrigues DQ, Ferreira VF, Marques IP, Santos FC, Cunha AC, Souza MC, Frugulhetti ICPP, Bou-Habib DC, Fontes CF (2009) Characterization of HIV-1 enzyme reverse transcriptase inhibition by the compound 6-chloro-1,4-dihydro-4-oxo-1-(beta-d-ribofuranosyl) quinoline-3-carboxylic acid through kinetic and in silico studies. Curr HIV Res 7(3):327-335
53. Souza TM, Salluh JI, Bozza FA, Mesquita M, Soares M, Motta FC, Pitrowsky MT, Oliveira ML, Mishin VP, Gubareva LV, Whitney A, Rocco SA, Gonçalves VM, Marques VP, Velasco E, Siqueira MM (2010) H1N1pdm influenza infection in hospitalized cancer patients: clinical evolution and viral analysis. PLoS One 5(11):e14158
54. Stierand K, Rarey M (2010) Drawing the PDB: protein-ligand complexes in two dimensions. ACS Med Chem Lett 1(9):540-545
55. Thomsen R, Christensen MH (2006) MolDock: a new technique for high-accuracy molecular docking. J Med Chem 49(11):3315-3321
56. Wang X-L, Wan K, Zhou C-H (2010) Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities. Eur J Med Chem 45(10):4631-4639
57. World Health Organization (2009) CDC protocol of realtime RTPCR for influenza A(H1N1) http://www.who.int/csr/resources/publications/swineflu/ CDCRealtimeRTPCR-SwineH1Assay-2009-20090430.pdf. Accessed 30 Apr 2009
58. Yan S-J, Liu Y-J, Chen Y-L, Liu L, Lin J (2010) An efficient one-pot synthesis of heterocycle-fused 1,2,3-triazole derivatives as anti-cancer agents. Bioorg Med Chem Lett 20(17):5225-5228
59. Zhan P, Chen X, Li X, Li D, Tian Y, Chen W, Pannecouque C, De Clercq E, Liu X (2011) Arylazolylthioacetanilide. Part 8: Design, synthesis and biological evaluation of novel 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N- arylacetamides as potent HIV-1 inhibitors. Eur J Med Chem 46(10):5039-5045