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Synthesis of 1-(2-naphthoyl) benzotriazoles as photoactivated DNA cleaving agents

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References Cited

  1. Danishefsky, S. J., Shair, M. D., Yoon, T., Total synthesis of (+)-Dynemicin A,Angew. Chem. Int. Ed. Engl., 34, 1721–1723 (1995).

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  3. Goldberg, I. H., Chin, D-H, Identification of the active species responsible for Holo-Neocarzinostatin-Induced DNA Cleavage.J. Am. Chem. Soc., 115, 9341–9342 (1993).

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  6. Saito, I., Takayama, M., Skurai, T., Photogeneration of Carbocation via Intramolecular Electron Transfer: Photoinduced DNA Alkylation,J. Am. Chem. Soc., 116, 2653–2654 (1994).

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  8. Wender, P. A., Kelly, R. C., Beckham, S., Miller, B. L., Studies on DNA-cleaving agents: computer modeling analysis of the mechanism of activation and cleavage of dynemicin-oligonucleotide complexes,Proc. Natl. Acad. Sci. USA, 88, 8835–8839 (1991).

  9. Spectral data of2;1H NMR (CDCl3): 8.88 (s, 1H), 8. 46 (d, J=8.4, 1H), 8.24 (dd, J=8.4, 1.8, 1H), 8.21 (d, J=8.4, 1H), 8.05 (d, 6 Hz, 1H), 8.03 (d, J=8.1, 1H), 7.96 (d, J=8.4, 1H), 7.78–7.56 (m, 4H)

  10. Spectral data of4;1H NMR (DMSO-d6): 8.57 (s, 1H), 8.04 (d, J=8.7, 1H), 7.99 (d, J=8.7, 1H) 4.34 (t, J=6. 3, 2H), 3.48 (t, J=6.3, 2H), 1.80 (m, 2H), 1.59 (m, 2H)

  11. Spectral data of5;1H NMR (CDCl3): 8.76 (s, 1H), 8. 16 (d, J=8.7, 1H), 7.95 (d, J=8.7, 1H), 4.45 (t, J=6.0, 2H), 4.32 (t, J=6, 2H), 4.12 (s, 2H), 1.92 (m, 4H)

  12. Spectral data of7;1H NMR (CDCl3): 8.91 (s, 1H, 4), 8.90 (d, J=0.6, 1H, 11), 8.50 (dd, J=8.1, J=0.6, 1H, 6), 8.42 (dd, J-8.7, J=1.5, 1H, 7), 8.24 (dd, J=8.7, J =1.8, 1H, 3′), 8.06 (d, J=7.5, 1H, 8′), 8.05 (d, J=8.4, 1H, 4′), 7.97 (d, J=7.8), 7.70–7.61 (m, 2H, 6′, 7′), 4. 47 (t, J=6, 2H, 1″), 4.32 (t, J=6, 2H, 4″), 4.10 (s, 2H, ClCH2−) 1.95–1.91 (m 4H, 2″, 3″)

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Correspondence to Jae Wook Yang.

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Yang, J.W., Wender, P.A. Synthesis of 1-(2-naphthoyl) benzotriazoles as photoactivated DNA cleaving agents. Arch. Pharm. Res. 20, 197–199 (1997). https://doi.org/10.1007/BF02974011

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Key words

  • benzotriazole
  • benzotriazole-5-carboxylic acid
  • photoactivated DNA cleaving agents