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Volumn 70, Issue 9, 2005, Pages 3724-3726

N6-arylation of 2′-deoxyadenosine via copper-catalyzed direct coupling with aryl halides

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; COPPER; DERIVATIVES; ELECTRONIC STRUCTURE;

EID: 17744362897     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040284w     Document Type: Article
Times cited : (29)

References (41)
  • 2
    • 13244296625 scopus 로고    scopus 로고
    • Monographs on the Evaluation of the Carcinogenic Risks to Humans
    • IARC: Lyon, France
    • International Agency for Research on Cancer. Monographs on the Evaluation of the Carcinogenic Risks to Humans. Tobacco Smoke and Involuntary Smoking; IARC: Lyon, France, 2004; Vol. 83.
    • (2004) Tobacco Smoke and Involuntary Smoking , pp. 83
  • 5
    • 0344402706 scopus 로고
    • Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans
    • IARC: Lyon, France
    • International Agency for Research on Cancer. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Polynuclear Aromatic Compounds, Part 1, Chemical, Environmental and Experimental Data; IARC: Lyon, France, 1983; Vol. 32.
    • (1983) Polynuclear Aromatic Compounds, Part 1, Chemical, Environmental and Experimental Data , vol.32
  • 8
    • 0028707724 scopus 로고
    • Hemminki, K., Dipple, A., Segerbäck, D., Kadulbar, F. F., Shuker, D., Bartsch, H., Eds.; IARC Scientific Publication No. 125; IARC: Lyon, France
    • Dipple, A. In DNA Adducts: Identification and Biological Significance; Hemminki, K., Dipple, A., Segerbäck, D., Kadulbar, F. F., Shuker, D., Bartsch, H., Eds.; IARC Scientific Publication No. 125; IARC: Lyon, France, 1994; pp 107-129.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 107-129
    • Dipple, A.1
  • 10
    • 0023835621 scopus 로고
    • Smithgall, T. E.; Harvey, R. G.; Penning, T. M. J. Biol. Chem. 1986, 261, 6184-6191; Cancer Res. 1988, 48, 1227-1232; J. Biol. Chem. 1988, 263, 1814-1820.
    • (1988) Cancer Res. , vol.48 , pp. 1227-1232
  • 11
    • 0023907050 scopus 로고
    • Smithgall, T. E.; Harvey, R. G.; Penning, T. M. J. Biol. Chem. 1986, 261, 6184-6191; Cancer Res. 1988, 48, 1227-1232; J. Biol. Chem. 1988, 263, 1814-1820.
    • (1988) J. Biol. Chem. , vol.263 , pp. 1814-1820
  • 12
    • 0030065647 scopus 로고    scopus 로고
    • Penning, T. M.; Onishi, S. T.; Onishi, T.; Harvey, R. G.; Chem. Res. Toxicol. 1996, 9, 84-92. Flowers, L.; Onishi, S. T.; Penning, T. M. Biochemistry 1997, 36, 8640. Shou, M.; Harvey, R. G.; Penning, T. M. Carcinogenesis 1993, 14, 475-482.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 84-92
    • Penning, T.M.1    Onishi, S.T.2    Onishi, T.3    Harvey, R.G.4
  • 13
    • 0342981512 scopus 로고    scopus 로고
    • Penning, T. M.; Onishi, S. T.; Onishi, T.; Harvey, R. G.; Chem. Res. Toxicol. 1996, 9, 84-92. Flowers, L.; Onishi, S. T.; Penning, T. M. Biochemistry 1997, 36, 8640. Shou, M.; Harvey, R. G.; Penning, T. M. Carcinogenesis 1993, 14, 475-482.
    • (1997) Biochemistry , vol.36 , pp. 8640
    • Flowers, L.1    Onishi, S.T.2    Penning, T.M.3
  • 14
    • 0027281455 scopus 로고
    • Penning, T. M.; Onishi, S. T.; Onishi, T.; Harvey, R. G.; Chem. Res. Toxicol. 1996, 9, 84-92. Flowers, L.; Onishi, S. T.; Penning, T. M. Biochemistry 1997, 36, 8640. Shou, M.; Harvey, R. G.; Penning, T. M. Carcinogenesis 1993, 14, 475-482.
    • (1993) Carcinogenesis , vol.14 , pp. 475-482
    • Shou, M.1    Harvey, R.G.2    Penning, T.M.3
  • 15
    • 0029080079 scopus 로고
    • A third mechanistic pathway that involves activation of PAHs by CYP peroxidase to generate PAH radical-cations that combine with DNA to form unstable adducts lost by depurination has also been proposed: Cavalieri, E. L.; Rogan, E. Xenobiotica 1995, 25, 677. The relevance of this mechanism is disputed: Melendez-Colon, V.; Luch, A.; Seidel, A.; Baird, W. Carcinogenesis 1999, 20, 1885.
    • (1995) Xenobiotica , vol.25 , pp. 677
    • Cavalieri, E.L.1    Rogan, E.2
  • 16
    • 0032832051 scopus 로고    scopus 로고
    • A third mechanistic pathway that involves activation of PAHs by CYP peroxidase to generate PAH radical-cations that combine with DNA to form unstable adducts lost by depurination has also been proposed: Cavalieri, E. L.; Rogan, E. Xenobiotica 1995, 25, 677. The relevance of this mechanism is disputed: Melendez-Colon, V.; Luch, A.; Seidel, A.; Baird, W. Carcinogenesis 1999, 20, 1885.
    • (1999) Carcinogenesis , vol.20 , pp. 1885
    • Melendez-Colon, V.1    Luch, A.2    Seidel, A.3    Baird, W.4
  • 19
    • 17744395054 scopus 로고    scopus 로고
    • note
    • The synthetic route to the PAH quinone adducts of 2′- deoxyribonucleosides entails coupling of protected halogen-substituted derivatives of the PAH quinones (or the corresponding catechols) with dA or dG, or their derivatives, followed by deprotection (and in the case of the catechols reoxidation back to quinones).
  • 28
    • 0008165462 scopus 로고    scopus 로고
    • Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
    • (1999) J. Organomet. Chem. , vol.576 , pp. 125-146
    • Yang, B.H.1    Buchwald, S.L.2
  • 29
    • 0001038733 scopus 로고    scopus 로고
    • Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 805-818
    • Wolfe, J.P.1    Wagaw, S.2    Marcoux, J.-F.3    Buchwald, S.L.4
  • 30
    • 0032541260 scopus 로고    scopus 로고
    • Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2046-2067
    • Hartwig, J.F.1
  • 34
  • 40
    • 0037132666 scopus 로고    scopus 로고
    • Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14844-14845. Xu, G.; Sygula, A.; Marcinow, Z.; Rabideau, P. W. Tetrahedron Lett. 2000, 41, 9931-9934.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 14844-14845
    • Klapars, A.1    Buchwald, S.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.