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Synthesis, Physico-Chemical and Spectroscopic Properties of PAC and Metabolites

Synthesis of the Diol Epoxide Metabolites of Carcinogenic PAH

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Pages 43-50 | Published online: 22 Sep 2006

References

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  • Structural assignment of 13 was consistent with its 300 MHz proton NMR spectrum (DMSO-d6); δ 3. 99 (s, 2, CH2), 4. 52 (br s, 1, H2), 4. 86 (t, 1, H1), 5. 19 (d, 1, OH), 5. 50 (d, 1, OH), 5. 90 (d, 1, H3), 7. 57–7. 62 (m, 2, H7, 8), 7. 64 (s, 1, H5), 7. 69 (d, 1, H11), 7. 97 (dd, 1, H6), 8. 41 (d, 1, H10), 8. 68 (d, 1, H9); J 1, 2 = 6, J 2, 3 = 1. 6, J 8, 9 = 7. 2, J 6, 7 = 7. 5, J 6, 8 = 1. 6, J10, 11 = 8. 2 Hz
  • Reference 1, Chap. 13
  • Amin , S. , Camnzo , J. , Huie , K. and Hecht , S. S. 1984 . J. Org. Chem. , 49 : 381
  • Liu , L. B. , Yang , B. W. , Katz , T. J. and Poindexter , M. K. 1991 . J. Org. Chem. , 56 : 3769
  • The proton NMR spectrum of 19 agrees with its assigned structure (300MHz in DMSO-d6); δ 4. 36 (m, 3, H4, 7), 4. 81 (dd, 1, H6), 5. 25 (d, 1, OH), 5. 62 (d, 1, OH), 6. 11 (dd, 1, H8), 7. 26 (dd, 1, H9), 7. 65 (dd, 1, H2), 7. 75 (d, 1, H2), 7. 87 (d, 1, H1), 7. 90 (d, 1, H11), 7. 99 (s, 1, H5), 8. 12 (d, 1, H10); J 1, 2 = 8. 0, J 2, 3 = 7. 0, J 6, 7 = 10, J 8, 9 = 10, J 10, 11 = 9 Hz
  • Glatt , H. , Piée , A. , Pauly , K. , Steinbrecher , T. , Schrode , R. , Oesch , F. and Seidel , A. 1991 . Cancer Res. , 51 : 1659
  • Clar , E. , McAndrew , B. A. and Stephen , J. F. 1970 . Tetrahedron , 26 : 5465
  • Clar reported benzo[s]picene to be an oil. However, we obtained it as a crystalline solid with a melting point of 195. 5–197. 5°C
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  • The proton NMR spectrum of 28 fully agreed with its assignment (300 MHz in DMSO-d6/D2O): δ 4. 75 (d, 1, H3), 4. 84 (d, 1, H4), 6. 46 (dd, 1, H2), 7. 38 (dd, 1, H1), 7. 86–7. 95 (m, 4, H10, 11, 14, 15), 8. 15 (d, 1, H5), 8. 34 (d, 2, H7, 8) 8. 61 (d, 1, H6), 8. 90–9. 07(m, 3, H12, 13, 16); J 1, 2 = 10. 4, J 1, 3 = 1. 7, J 2, 3 = 2. 0, J 3, 4 = 10. 84 Hz

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