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Volumn 17, Issue 1, 2012, Pages 179-190

Synthesis of 1,4-disubstituted mono and bis-triazolocarboacyclonucleoside analogues of 9-(4-hydroxybutyl)guanine by Cu(I)-catalyzed click azide-alkyne cycloaddition

Author keywords

1,2,3 triazole; 1,2,3 bis triazoles; 1,3 dipolar cycloaddition; Antibacterial activities; Click azide alkyne; Microwave assisted synthesis

Indexed keywords

9 (4 HYDROXYBUTYL)GUANINE; 9-(4-HYDROXYBUTYL)GUANINE; ACICLOVIR; ALKYNE; ANTIINFECTIVE AGENT; ANTIVIRUS AGENT; AZIDE; COPPER; DRUG DERIVATIVE;

EID: 84856171086     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17010179     Document Type: Article
Times cited : (24)

References (37)
  • 2
    • 0026523623 scopus 로고
    • HIV inhibitors targeted at the reverse transcriptase
    • Clercq, E.D. HIV inhibitors targeted at the reverse transcriptase AIDS Res. Hum. Retrovirus. 1992, 8, 119-134.
    • (1992) AIDS Res. Hum. Retrovirus. , vol.8 , pp. 119-134
    • Clercq, E.D.1
  • 3
    • 0033406371 scopus 로고    scopus 로고
    • EASL international consensus conference on hepatitis C. Consensus statement
    • EASL International Consensus Conference on Hepatitis C. Consensus Statement. J. Hepatol. 1999, 31, 3-8.
    • (1999) J. Hepatol. , vol.31 , pp. 3-8
  • 4
    • 0029120163 scopus 로고
    • Stereoselective synthesis, chemistry and antiviral evaluation of 1-(2,3-dideoxy-3-C-hydroxymethyl-beta-D-threo-pentofuranosyl)thymine derivatives
    • Wengel, J.; Schinazi, R.F.; Caruthers, M.H. Stereoselective synthesis, chemistry and antiviral evaluation of 1-(2,3-dideoxy-3-C-hydroxymethyl-beta-D- threo-pentofuranosyl)thymine derivatives. Bioorg. Med. Chem. 1995, 3, 1223-1229.
    • (1995) Bioorg. Med. Chem. , vol.3 , pp. 1223-1229
    • Wengel, J.1    Schinazi, R.F.2    Caruthers, M.H.3
  • 5
    • 15444359037 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of novel acyclic nucleosides: Discovery of a cyclopropyl nucleoside with potent inhibitory activity against herpesviruses
    • Sekiyama, T.; Hatsuya, S.; Tanaka, Y.; Uduyama, M.; Ono, N.; Iwayama, S.; Oikawa, M.; Suzuki, K.; Okunishi, M.; Tsuji, T. Synthesis and antiviral activity of novel acyclic nucleosides: Discovery of a cyclopropyl nucleoside with potent inhibitory activity against herpesviruses. J. Med. Chem. 1998, 41, 1248-1298.
    • (1998) J. Med. Chem. , vol.41 , pp. 1248-1298
    • Sekiyama, T.1    Hatsuya, S.2    Tanaka, Y.3    Uduyama, M.4    Ono, N.5    Iwayama, S.6    Oikawa, M.7    Suzuki, K.8    Okunishi, M.9    Tsuji, T.10
  • 6
    • 0024991964 scopus 로고
    • Computer-assisted structure-activity correlations of dideoxynucleoside analogs as potential anti-HIV drugs
    • DOI 10.1016/0166-3542(90)90030-B
    • Nasr, M.; Litterst, C.; McGowan, J. Computer-assisted structure-activity correlations of dideoxynucleoside analogs as potential anti-HIV drugs. Antiviral Res. 1990, 14, 125-148. (Pubitemid 20300731)
    • (1990) Antiviral Research , vol.14 , Issue.3 , pp. 125-148
    • Nasr, M.1    Litterst, C.2    McGowan, J.3
  • 7
    • 0032853663 scopus 로고    scopus 로고
    • Nucleoside synthesis mediated by glycosyl transferring enzymes
    • DOI 10.1006/bioo.1998.1127
    • Prasad, A.K.; Trikha, S.; Parmar, V.S. Nucleoside synthesis mediated by glycosyl transferring enzymes. Bioorg. Chem. 1999, 27, 135-154. (Pubitemid 29434140)
    • (1999) Bioorganic Chemistry , vol.27 , Issue.2 , pp. 135-154
    • Prasad, A.K.1    Trikha, S.2    Parmar, V.S.3
  • 8
    • 0022532716 scopus 로고
    • Chemistry and antiviral activities of acyclonucleosides
    • Chu, C.K.; Cutler, S.J.; Chu, C.K.; Cutler, S.J. Chemistry and antiviral activities of acyclonucleosides. J. Heterocycl. Chem. 1986, 23, 289-319. (Pubitemid 16019327)
    • (1986) Journal of Heterocyclic Chemistry , vol.23 , Issue.2 , pp. 289-319
    • Chu, C.K.1    Cutler, S.J.2
  • 9
    • 0025111176 scopus 로고
    • Synthesis of acyclic nucleoside analogs of 6-substituted 2-aminopurines and 2-amino-8-azapurines
    • Parkanyi, C.; Yuan, H.L. Synthesis of acyclic nucleoside analogs of 6-substituted 2-aminopurines and 2-amino-8-azapurines. J. Heterocycl. Chem. 1990, 27, 1409-1413. (Pubitemid 20305928)
    • (1990) Journal of Heterocyclic Chemistry , vol.27 , Issue.5 , pp. 1409-1413
    • Parkanyi, C.1    Yuan, H.L.2
  • 12
    • 33748595818 scopus 로고    scopus 로고
    • Novel synthesis of purine acyclonucleosides possessing a chiral 9-hydroxyalkyl group by sugar modification of 9-D-ribitylpurines
    • Hirota, K.; Monguchi, Y.; Sajiki, H.; Sako, M.; Kitada, Y. Novel synthesis of purine acyclonucleosides possessing a chiral 9-hydroxyalkyl group by sugar modification of 9-Dribitylpurines. J. Chem. Soc. Perkin Trans. 1 1998, 941-946. (Pubitemid 128758132)
    • (1998) Journal of the Chemical Society - Perkin Transactions 1 , Issue.5 , pp. 941-946
    • Hirota, K.1    Monguchi, Y.2    Sajiki, H.3    Sako, M.4    Kitade, Y.5
  • 14
    • 33750826586 scopus 로고    scopus 로고
    • Acyclonucleosides: Part 3. tri-,tetra-,and pentaseco-nucleosides
    • El Ashry, E.S.H.; El Kilany, Y. Acyclonucleosides: Part 3. tri-, tetra-, and pentaseco-nucleosides. Adv. Heterocycl. Chem. 1998, 69, 129-215.
    • (1998) Adv. Heterocycl. Chem. , vol.69 , pp. 129-215
    • El Ashry, E.S.H.1    El Kilany, Y.2
  • 16
  • 17
    • 0031823828 scopus 로고    scopus 로고
    • Acyclo c-nucleoside analogs. Regioselective annellation of a triazole ring to 5-methyl-1,2,4-triazino[5,6-b]indole and formation of certain 3-poly hydroxyalkyl derivatives
    • Rashed, N.; Abdel Hamid, H.; Ramadan, E.S.; El Ashry, E.S.H. Acyclo C-nucleoside analogues. Regioselective anellation of a triazole ring to 5-methyl-1,2,4-triazino[5,6-b]indole and formation of certain 3-poly hydroxyalkyl derivatives. Nucleos. Nucleot. 1998, 17, 1373-1384. (Pubitemid 28332289)
    • (1998) Nucleosides and Nucleotides , vol.17 , Issue.8 , pp. 1373-1384
    • Rashed, N.1    Hamid, H.A.2    Ramadan, E.S.3    El Ashry, E.S.H.4
  • 18
    • 85023029844 scopus 로고
    • Dehydrative ring-closure of 3-substituted 2-quinoxalinones to give fused and nonfused pyrazoloquinoxalines
    • El Ashry, E.S.H.; El Kholy, I.E.; El Kilany, Y. Dehydrative ring-closure of 3-substituted 2-quinoxalinones to give fused and nonfused pyrazoloquinoxalines. Carbohydr. Res 1978, 60, 303-314.
    • (1978) Carbohydr. Res , vol.60 , pp. 303-314
    • El Ashry, E.S.H.1    El Kholy, I.E.2    El Kilany, Y.3
  • 19
    • 0015523596 scopus 로고
    • Broadspectrum antiviral activity of Virazole: 1-beta-D-Ribofuranosyl-1,2, 4-triazole-3-carboxamide
    • Sidwell, R.W.; Huffman, J.H.; Khare, G.P.; Allen, L.B.; Witkowski, J.T.; Robins, R.K. Broadspectrum antiviral activity of Virazole: 1-beta-D- Ribofuranosyl-1,2,4-triazole-3-carboxamide. Science 1972, 177, 705-706.
    • (1972) Science , vol.177 , pp. 705-706
    • Sidwell, R.W.1    Huffman, J.H.2    Khare, G.P.3    Allen, L.B.4    Witkowski, J.T.5    Robins, R.K.6
  • 21
    • 11544346529 scopus 로고    scopus 로고
    • Asymmetric 1,3-dipolar cycloaddition reactions
    • Gothelf, K.V.; Jørgensen, K.A. Asymmetric 1,3-dipolar cycloaddition reactions. Chem. Rev. 1998, 98, 863-910.
    • (1998) Chem. Rev. , vol.98 , pp. 863-910
    • Gothelf, K.V.1    Jørgensen, K.A.2
  • 23
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
    • Rostovtsev Green, V.V.L.G.; Fokin, V.V.; Sharpless, K.B. Stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes. Angew. Chem. Int. Ed. 2002, 41, 2596-2599. (Pubitemid 34803480)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.14 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 24
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • DOI 10.1021/jo011148j
    • Tornfe, C.W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-talyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057-3064. (Pubitemid 34457265)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.9 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 26
    • 0141518157 scopus 로고    scopus 로고
    • Click linker: Efficient and high-yielding synthesis of a new family of SPOS resins by 1,3-dipolar cycloaddition
    • DOI 10.1021/ol034520l
    • Lober, S.; Rodriguez-Loaiza, P.; Gmeiner, P. Click linker: Efficient and high-yielding synthesis of a new family of SPOS resins by 1,3-dipolar cycloaddition. Org. Lett. 2003, 5, 1753-1755. (Pubitemid 37162021)
    • (2003) Organic Letters , vol.5 , Issue.10 , pp. 1753-1755
    • Lober, S.1    Rodriguez-Loaiza, P.2    Gmeiner, P.3
  • 28
    • 2442698173 scopus 로고    scopus 로고
    • Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited
    • DOI 10.1021/ol0499203
    • Krasinski, A.; Fokin, V.V.; Sharpless, K.B. Direct synthesis of 1,5-disubstituted-4-magnesio- 1,2,3-triazoles, revisited. Org. Lett. 2004, 6, 1237-1240. (Pubitemid 38692031)
    • (2004) Organic Letters , vol.6 , Issue.8 , pp. 1237-1240
    • Krasinski, A.1    Fokin, V.V.2    Sharpless, K.B.3
  • 29
    • 0038541849 scopus 로고    scopus 로고
    • Synthesis of triazoles from nonactivated terminal alkynes via the three-component coupling reaction using a Pd(0)-Cu(I) bimetallic catalyst
    • DOI 10.1021/ja034191s
    • Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. Synthesis of triazoles from nonactivated terminal alkynes via the three-component coupling reaction using a Pd(0)-Cu(I) bimetallic catalyst. J. Am. Chem. Soc. 2003, 125, 7786-7787. (Pubitemid 36782140)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.26 , pp. 7786-7787
    • Kamijo, S.1    Jin, T.2    Huo, Z.3    Yamamoto, Y.4
  • 30
    • 1842451887 scopus 로고    scopus 로고
    • A One-Pot Procedure for the Regiocontrolled Synthesis of Allyltriazoles via the Pd-Cu Bimetallic Catalyzed Three-Component Coupling Reaction of Nonactivated Terminal Alkynes, Allyl Carbonate, and Trimethylsilyl Azide
    • DOI 10.1021/jo035292b
    • Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. A one-pot procedure for the regiocontrolled synthesis of allyltriazoles via the Pd-Cu bimetallic catalyzed three-component coupling reaction of nonactivated terminal alkynes, allyl carbonate, and trimethylsilyl azide. J. Org. Chem. 2004, 69, 2386-2393. (Pubitemid 38419050)
    • (2004) Journal of Organic Chemistry , vol.69 , Issue.7 , pp. 2386-2393
    • Kamijo, S.1    Jin, T.2    Huo, Z.3    Yamamoto, Y.4
  • 31
    • 23944462604 scopus 로고    scopus 로고
    • General synthesis of (1-substituted-1H-1,2,3-triazol-4-ylmethyl)- dialkylamines via a copper(I)-catalyzed three-component reaction in water
    • DOI 10.1016/j.tet.2005.07.060, PII S0040402005012482
    • Yan, Z.Y.; Zhao, Y.B.; Fan, M.J.; Liu, W.M.; M.Liang, Y. General synthesis of (1-substituted- 1H-1,2,3-triazol-4-ylmethyl)-dialkylamines via a copper(I)-catalyzed three-component reaction in water. Tetrahedron 2005, 61, 9331-9337. (Pubitemid 41206493)
    • (2005) Tetrahedron , vol.61 , Issue.39 , pp. 9331-9337
    • Yan, Z.-Y.1    Zhao, Y.-B.2    Fan, M.-J.3    Liu, W.-M.4    Liang, Y.-M.5
  • 32
    • 51449095749 scopus 로고    scopus 로고
    • Nucleosides and oligonucleotides containing 1,2,3-triazole residues with nucleobase tethers: Synthesis via the azide-alkyne 'click' reaction
    • Chittepu, P.; Sirivolu, V.R.; Seela, F. Nucleosides and oligonucleotides containing 1,2,3-triazole residues with nucleobase tethers: Synthesis via the azide-alkyne 'click' reaction. Bioorg. Med. Chem. 2008, 16, 8427-8439.
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 8427-8439
    • Chittepu, P.1    Sirivolu, V.R.2    Seela, F.3
  • 33
    • 35648931013 scopus 로고    scopus 로고
    • Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides
    • DOI 10.1016/j.bmcl.2007.08.077, PII S0960894X07011407
    • El Akri, K.; Bougrin, K.; Balzarini, B.J.; Faraj, A.; Benhida, R. Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides. Bioorg. Med. Chem. Lett. 2007, 17, 6656-6659. (Pubitemid 350030884)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.23 , pp. 6656-6659
    • El Akri, K.1    Bougrin, K.2    Balzarini, J.3    Faraj, A.4    Benhida, R.5
  • 34
    • 77953200029 scopus 로고    scopus 로고
    • Microwave-assisted click chemistry: Synthesis of mono and bis-1,2,3-triazole acyclonucleoside analogues of ACV via copper(I)-catalyzed cycloaddition
    • Krim, J.; Sillahi, B.; Taourirte, M.; Rakib, E.M.; Engels, J.W. Microwave-assisted click chemistry: Synthesis of mono and bis-1,2,3-triazole acyclonucleoside analogues of ACV via copper(I)-catalyzed cycloaddition. ARKIVOC 2009, xiii, 142-152.
    • (2009) ARKIVOC , vol.13 , pp. 142-152
    • Krim, J.1    Sillahi, B.2    Taourirte, M.3    Rakib, E.M.4    Engels, J.W.5
  • 36
    • 0019818628 scopus 로고
    • Enzymatic phosphorylation of acyclic nucleoside analogs and correlations with antiherptetic activities
    • DOI 10.1016/0006-2952(81)90495-0
    • Keller, P.M.; FyfeJ, A.; Beauchamp, L.; Lubbers, C.M.; Furman, P.A.; Schaeffer, H.J.; Elion, G.B. Enzymatic phosphorylation of acyclic nucleoside analogs and correlations with antiherpetic activities. Biochem. Pharmacol. 1981, 30, 3071-3077. (Pubitemid 12229328)
    • (1981) Biochemical Pharmacology , vol.30 , Issue.22 , pp. 3071-3077
    • Keller, P.M.1    Fyfe, J.A.2    Beauchamp, L.3


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