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Volumn 53, Issue , 2012, Pages 220-228

Synthesis and antiviral evaluation of C5-substituted-(1,3-diyne)-2′- deoxyuridines

Author keywords

Anti VZV activity; Diyne scaffold; Nickel copper catalyzed C H activation; Nucleoside

Indexed keywords

5 (4 PHENYLBUTA 1,3 DIYNYL) 2' DEOXYURIDINE; 5 (6 HYDROXYHEPTA 1,3 DIYNYL) 2'' DEOXYURIDINE; 5 [4 (3 AMINOPHENYL)BUTA 1,3 DIYNYL] 2'' DEOXYURIDINE; 5 [4 (3,5 DIMETHOXYPHENYL)BUTA 1,3 DIYNYL] 2'' DEOXYURIDINE; 5 [4 (4 AMINOPHENYL)BUTA 1,3 DIYNYL] 2'' DEOXYURIDINE; 5 [4 (4 FLUORO 3 METHYLPHENYL)BUTA 1,3 DIYNYL] 2'' DEOXYURIDINE; 5 [4 (4 HEXYLPHENYL)BUTA 1,3 DIYNYL] 2'' DEOXYURIDINE; 5 [4 (4 NITROPHENYL)BUTA 1,3 DIYNYL] 2'' DEOXYURIDINE; 5 [4 (4 PROPYLPHENYL)PHENYLBUTA 1,3 DIYNYL] 2'' DEOXYURIDINE; 5 [4 (4 TRIFLUOROMETHOXYPHENYL)BUTA 1,3 DIYNYL] 2' DEOXYURIDINE; 5 [4 (CYCLOPROPYL)BUTA 1,3 DIYNYL] 2'' DEOXYURIDINE; 5 [4 (PYRIDIN 2 YL)BUTA 1,3 DIYNYL] 2'' DEOXYURIDINE; 5 [5 CYCLOPENTYLPENTA 1,3 DIYNYL] 2'' DEOXYURIDINE; 5 [5 HYDROPENTA1,3 DIYNYL] 2'' DEOXYURIDINE; 5 ETHYNYLDEOXYURIDINE; ALKYNE DERIVATIVE; ANTIVIRUS AGENT; C5 SUBSTITUTED(1,3 DIYNE) 2' DEOXYURIDINE; COPPER; DEOXYURIDINE DERIVATIVE; NICKEL; UNCLASSIFIED DRUG;

EID: 84861581552     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.04.001     Document Type: Article
Times cited : (18)

References (25)
  • 2
    • 0019184111 scopus 로고
    • Antiviral and antitumor activities of 5-substituted 2′- deoxyuridines
    • (review)
    • E. De Clercq Antiviral and antitumor activities of 5-substituted 2′-deoxyuridines Methods Find. Exp. Clin. Pharmacol. 2 1980 253 267 (review)
    • (1980) Methods Find. Exp. Clin. Pharmacol. , vol.2 , pp. 253-267
    • De Clercq, E.1
  • 3
    • 0035901674 scopus 로고    scopus 로고
    • High-density labelling of DNA: Preparation and characterization of the target material for single-molecule sequencing
    • S. Brakmann, and S. Lobermann High-density labelling of DNA: preparation and characterization of the target material for single-molecule sequencing Angew. Chem., Int. Ed. 40 2001 1427 1429
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 1427-1429
    • Brakmann, S.1    Lobermann, S.2
  • 4
    • 0037705457 scopus 로고    scopus 로고
    • Incorporation of reporter molecule-labeled nucleotides by DNA polymerases. I. Chemical synthesis of various reporter group-labeled 2′-deoxyribonucleoside-5′-triphosphates
    • G. Giller, T. Tasara, B. Angerer, K. Mühlegger, M. Amacker, and H. Winter Incorporation of reporter molecule-labeled nucleotides by DNA polymerases. I. Chemical synthesis of various reporter group-labeled 2′-deoxyribonucleoside-5′-triphosphates Nucleic Acids Res. 31 2003 2630 2635
    • (2003) Nucleic Acids Res. , vol.31 , pp. 2630-2635
    • Giller, G.1    Tasara, T.2    Angerer, B.3    Mühlegger, K.4    Amacker, M.5    Winter, H.6
  • 5
    • 0032122430 scopus 로고    scopus 로고
    • Hybridization properties of base-modified oligonucleotides within the double and triple helix motif
    • I. Luyten, and P. Herdewijn Hybridization properties of base-modified oligonucleotides within the double and triple helix motif Eur. J. Med. Chem. 33 1998 515 576
    • (1998) Eur. J. Med. Chem. , vol.33 , pp. 515-576
    • Luyten, I.1    Herdewijn, P.2
  • 6
    • 4444234581 scopus 로고    scopus 로고
    • Stabilizing or destabilizing oligodeoxynucleotide duplexes containing single 2′-deoxyuridine residues with 5-alkynyl substituents
    • T. Kottysch, C. Ahlborn, F. Brotzel, and C. Richert Stabilizing or destabilizing oligodeoxynucleotide duplexes containing single 2′-deoxyuridine residues with 5-alkynyl substituents Chem. Eur. J. 10 2004 4017 4028
    • (2004) Chem. Eur. J. , vol.10 , pp. 4017-4028
    • Kottysch, T.1    Ahlborn, C.2    Brotzel, F.3    Richert, C.4
  • 7
    • 7544248773 scopus 로고    scopus 로고
    • Discovery and development of BVDU (brivudin) as a therapeutic for the treatment of herpes zoster
    • (review)
    • E. De Clercq Discovery and development of BVDU (brivudin) as a therapeutic for the treatment of herpes zoster Biochem. Pharmacol. 68 2004 2301 2315 (review)
    • (2004) Biochem. Pharmacol. , vol.68 , pp. 2301-2315
    • De Clercq, E.1
  • 9
    • 0141545111 scopus 로고    scopus 로고
    • Substrate properties of C5-substituted pyrimidine 2′- deoxynucleoside 5′-triphosphates for thermostable DNA polymerases during PCR
    • M. Kuwahara, Y. Takahata, A. Shoji, A.N. Ozaki, H. Ozaki, and H. Sawai Substrate properties of C5-substituted pyrimidine 2′-deoxynucleoside 5′-triphosphates for thermostable DNA polymerases during PCR Bioorg. Med. Chem. Lett. 13 2003 3735 3738
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 3735-3738
    • Kuwahara, M.1    Takahata, Y.2    Shoji, A.3    Ozaki, A.N.4    Ozaki, H.5    Sawai, H.6
  • 10
    • 27444434251 scopus 로고    scopus 로고
    • Design and studies of novel 5-substituted alkynylpyrimidine nucleosides as potent inhibitors of mycobacteria
    • D. Rai, M. Johar, T. Manning, B. Agrawal, D.Y. Kunimoto, and R. Kumar Design and studies of novel 5-substituted alkynylpyrimidine nucleosides as potent inhibitors of mycobacteria J. Med. Chem. 48 2005 7012 7017
    • (2005) J. Med. Chem. , vol.48 , pp. 7012-7017
    • Rai, D.1    Johar, M.2    Manning, T.3    Agrawal, B.4    Kunimoto, D.Y.5    Kumar, R.6
  • 11
    • 33947141062 scopus 로고    scopus 로고
    • 5-Alkynyl-2′-deoxyuridines: Chromatography-free synthesis and cytotoxicity evaluation against human breast cancer cells
    • S. Meneni, I. Ott, C.D. Sergeant, A. Sniady, R. Gust, and R. Dembinski 5-Alkynyl-2′-deoxyuridines: chromatography-free synthesis and cytotoxicity evaluation against human breast cancer cells Bioorg. Med. Chem. 15 2007 3082 3088
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 3082-3088
    • Meneni, S.1    Ott, I.2    Sergeant, C.D.3    Sniady, A.4    Gust, R.5    Dembinski, R.6
  • 12
    • 0037944068 scopus 로고    scopus 로고
    • Palladium-assisted routes to nucleosides
    • (review)
    • I. Gillaizeau, Y. Saito, and L.A. Agrofoglio Palladium-assisted routes to nucleosides Chem. Rev. 103 2003 1875 1916 (review)
    • (2003) Chem. Rev. , vol.103 , pp. 1875-1916
    • Gillaizeau, I.1    Saito, Y.2    Agrofoglio, L.A.3
  • 14
    • 0141869063 scopus 로고    scopus 로고
    • A versatile modification of on-column oligodeoxynucleotides using a copper-catalyzed oxidative acetylenic coupling reaction
    • N. Minakawa, Y. Ono, and A. Matsuda A versatile modification of on-column oligodeoxynucleotides using a copper-catalyzed oxidative acetylenic coupling reaction J. Am. Chem. Soc. 125 2003 11545 11552
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 11545-11552
    • Minakawa, N.1    Ono, Y.2    Matsuda, A.3
  • 15
    • 33947227876 scopus 로고    scopus 로고
    • Naphthalenyl- and anthracenyl-ethynyl dT analogues as base discriminating fluorescent nucleosides and intramolecular energy transfer donors in oligonucleotide probes
    • Q. Xiao, R.T. Ranasinghe, AM.P. Tang, and T. Brown Naphthalenyl- and anthracenyl-ethynyl dT analogues as base discriminating fluorescent nucleosides and intramolecular energy transfer donors in oligonucleotide probes Tetrahedron 63 2007 3483 3490
    • (2007) Tetrahedron , vol.63 , pp. 3483-3490
    • Xiao, Q.1    Ranasinghe, R.T.2    Tang, A.P.3    Brown, T.4
  • 16
    • 0001155298 scopus 로고
    • Beiträge zur kenntniss des acetenylbenzols
    • C. Glaser Beiträge zur kenntniss des acetenylbenzols Ber. Dtsch. Chem. Ges 2 1869 422 424
    • (1869) Ber. Dtsch. Chem. Ges , vol.2 , pp. 422-424
    • Glaser, C.1
  • 17
    • 33947476790 scopus 로고
    • Oxidative coupling of acetylenes
    • A.S. Hay Oxidative coupling of acetylenes J. Org. Chem. 27 1962 3320 3321
    • (1962) J. Org. Chem. , vol.27 , pp. 3320-3321
    • Hay, A.S.1
  • 18
    • 37049049306 scopus 로고
    • Macrocyclic acetylenic compounds. Part I. Cyclotetradeca-1: 3-diyne and related compounds
    • G. Eglinton, and A.R. Galbraith Macrocyclic acetylenic compounds. Part I. Cyclotetradeca-1: 3-diyne and related compounds J. Chem. Soc. 1959 889 896
    • (1959) J. Chem. Soc. , pp. 889-896
    • Eglinton, G.1    Galbraith, A.R.2
  • 19
    • 78650913520 scopus 로고    scopus 로고
    • Consecutive one-pot Sonogashira-Glaser coupling sequence - Direct preparation of symmetrical diynes by sequential Pd/Cu catalysis
    • E. Merkul, D. Urselmann, and T.J.J. Müller Consecutive one-pot Sonogashira-Glaser coupling sequence - direct preparation of symmetrical diynes by sequential Pd/Cu catalysis Eur. J. Org. Chem. 2 2011 238 242
    • (2011) Eur. J. Org. Chem. , vol.2 , pp. 238-242
    • Merkul, E.1    Urselmann, D.2    Müller, T.J.J.3
  • 20
    • 33846358874 scopus 로고    scopus 로고
    • Cyclopalladated ferrocenylimines: Efficient catalysts for homocoupling and Sonogashira reaction of terminal alkynes
    • F. Yang, X. Cui, Y. Li, J. Zhang, G. Ren, and Y. Wu Cyclopalladated ferrocenylimines: efficient catalysts for homocoupling and Sonogashira reaction of terminal alkynes Tetrahedron 63 2007 1963 1969
    • (2007) Tetrahedron , vol.63 , pp. 1963-1969
    • Yang, F.1    Cui, X.2    Li, Y.3    Zhang, J.4    Ren, G.5    Wu, Y.6
  • 21
    • 0034604562 scopus 로고    scopus 로고
    • Acetylenic coupling: A powerful tool in molecular construction
    • (review)
    • P. Siemsen, R.C. Livingston, and F. Diederich Acetylenic coupling: a powerful tool in molecular construction Angew. Chem., Int. Ed. 39 2000 2632 (review)
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2632
    • Siemsen, P.1    Livingston, R.C.2    Diederich, F.3
  • 22
    • 0001938260 scopus 로고
    • Coupling of Acetylenes
    • H.G. Viehe, Marcel Dekker New York
    • P. Cadiot, and W. Chodkiewicz Coupling of Acetylenes H.G. Viehe, Chemistry of Acetylenes 1969 Marcel Dekker New York 597 647
    • (1969) Chemistry of Acetylenes , pp. 597-647
    • Cadiot, P.1    Chodkiewicz, W.2
  • 24
    • 35348991749 scopus 로고    scopus 로고
    • Ligand- and base-free synthesis of 1,3-diynes catalyzed by low loading of heterogeneous Pd/C and CuI
    • T. Kurita, M. Abe, T. Maegawa, Y. Monguchi, and H. Sajiki Ligand- and base-free synthesis of 1,3-diynes catalyzed by low loading of heterogeneous Pd/C and CuI Synlett 16 2007 2521 2524
    • (2007) Synlett , vol.16 , pp. 2521-2524
    • Kurita, T.1    Abe, M.2    Maegawa, T.3    Monguchi, Y.4    Sajiki, H.5
  • 25
    • 60849127613 scopus 로고    scopus 로고
    • 2 as the oxidant at room temperature: Facile syntheses of unsymmetric 1,3-diynes
    • 2 as the oxidant at room temperature: facile syntheses of unsymmetric 1,3-diynes Org. Lett. 11 2009 709 712
    • (2009) Org. Lett. , vol.11 , pp. 709-712
    • Yin, W.1    He, C.2    Chen, M.3    Zhang, H.4    Lei, A.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.