Synthesis of the possible carcinogenic dihydrodiol and diol epoxide of phthalazine

Tetrahedron

Volumn 61, Issue 6, 2005, Pages 1545-1550

  Özer, Galip ^a   Saracoglu, Nurullah ^a   Menzek, Abdullah ^a   Balci, Metin ^b  

^a ATATÜRK UNIVERSITY   (Turkey)

^b MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Cycloaddition; Dihydrodiol; Epoxydiol; Photooxygenation; Phthalazine; Tetrazine

Indexed keywords

1,4 DIHYDROPYRIDAZINE; ALCOHOL DERIVATIVE; ALKADIENE; ALKENE DERIVATIVE; BENZENE; CARCINOGEN; DICARBOXYLIC ACID DERIVATIVE; DIHYDRODIOL; DIMETHYL 1,2,4,5 TETRAZINE 3,6 DICARBOXYLATE; DIOL EPOXIDE; HYDROXYL GROUP; MANGANESE OXIDE; PHTHALAZINE DERIVATIVE; PYRIDAZINE DERIVATIVE; TETRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CARCINOGENICITY; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; DIELS ALDER REACTION; OXIDATION KINETICS; PHOTOOXIDATION; PRIORITY JOURNAL;

BETULACEAE;

EID: 12344277636     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.11.071     Document Type: Article

References (37)

1. (a) Review: R.G. Harvey Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity 1991 Cambridge University Cambridge, England Chapters 3 and 4
2. D.H. Phillips Nature 303 1983 468 472
3. R.G. Harvey, and F.B. Dunne Nature (London) 273 1978 566
4. C.B. Huggins, J. Pataki, and R.G. Harvey Proc. Natl. Acad. Sci. U.S.A. 58 1967 2253
5. D.R. Bushman, J.M. Sayer, D.R. Boyd, and D.M. Jerina J. Am. Chem. Soc. 111 1989 2688 2691
6. R.E. Lehr, A.W. Wood, W. Levin, A.H. Conney, and D.M. Jerina S.K. Yang B.D. Silverman Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships 1988 CRC Boca Raton, FL 31 58
7. S.K. Agarwal, D.R. Boyd, H.P. Porter, W.B. Jennings, S.J. Grossman, and D.M. Jerina Tetrahedron Lett. 27 1986 4253 4256
8. W. Levin, A.W. Wood, R.L. Chang, S. Kumar, H. Yagii, D.M. Jerina, R.E. Lehr, and A.H. Conney Cancer Res. 43 1983 4625 4628
9. D.M. Jerina, J.W. Daly, B. Witkop, P. Zaltman-Nirenberg, and S. Udenfriend J. Am. Chem. Soc. 90 1968 6525 6527
10. T.K. Kato, Y.K. Saeki, and A. Hakura Mutat. Res. 439 1999 149 157
11. S. Kumar, P. Kole, S.K. Balani, and D.M. Jerina J. Org. Chem. 57 1992 2784 2787
12. E.J. Lavoie, E.A. Adams, A. Shigematsu, and D. Hoffmann Carcinogenesis 4 1983 1169 1173
13. A. Dipple, R.C. Moschel, and C.A. Bigger E.C. Searle Chemical Carcinogens 2nd ed. ACS Monograph 182 Vol. 2 1984 American Chemical Society Washington, DC 41 163
14. S. Kumar, and N.L. Agarwal J. Org. Chem. 51 1986 2445 2449
15. M. Nordquist, D.R. Thakker, H. Yagi, R.E. Lehr, A.W. Wood, W. Lewin, A.H. Conney, and D.M. Jerina R.S. Bhatnagar Molecular Basis of Environmental Toxicity 1980 Ann Arbor Science Ann Arbor, MI 329 357
16. J.M. Sayer, R.E. Lehr, D.L. Whalen, H. Yagi, and D.M. Jerina Tetrahedron Lett. 23 1982 4431 4434
17. R.E. Lehr, and D.M. Jerina Tetrahedron Lett. 24 1983 27 30
18. I.A. Smith, and P.G. Seybold J. Heterocycl. Chem. 14 1979 421
19. R.E. Lehr, A.W. Wood, W. Levin, A.H. Conney, and D.M. Jerina S.K. Yang B.D. Silverman Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships 1988 CRC Boca Raton, FL 31 58
20. R.E. Lehr, and D.M. Jerina Tetrahedron Lett. 24 1983 27 30
21. I.A. Smith, and P.G. Seybold J. Heterocycl. Chem. 16 1979 421 425
22. (a) For a review see: L. Dale, and D.L. Boger Tetrahedron 39 1983 2869 2939
23. M. Balci, N. Saraçoǧlu, and A. Menzek Tetrahedron Lett. 37 1996 921 924
24. G. Özer, N. Saraçoǧlu, and M. Balci Heterocycles 53 2000 761 764
25. G. Özer, N. Saraçoǧlu, and M. Balci J. Org. Chem. 68 2003 7009 7015
26. D.R. Boyd, N.D. Sharma, S.A. Barr, H. Dalton, J. Chima, G. Whited, and R. Seemayer J. Am. Chem. Soc. 116 1994 1147 1148
27. H. Seçen, S. Gültekin, Y. Sütbeyaz, and M. Balci Synth. Commun. 24 1994 2103 2108
28. P.E. Manni, and J.E. Sinsheimer J. Pharm. Sci. 54 1965 1541
29. S.V. Ley, and A.J. Redgrave Synlett 7 1990 393 394
30. K. Hayakawa, M. Aso, and K. Kanematsu J. Org. Chem. 50 1985 2036 2040
31. Y. Tamura, T. Yakura, H. Tohma, K. Kikuchi, and Y. Kita Synthesis 1989 126 127
32. A. Varvoglis Tetrahedron 53 1997 1179 1255
33. J.W. Keller, and C. Heidelberger J. Am. Chem. Soc. 98 1976 2328 2335
34. P.Y. Bruice, T.C. Bruice, P.M. Dansette, H.G. Selander, H. Yagi, and D.M. Jerina J. Am. Chem. Soc. 98 1976 2965 2969
35. R.G. Harvey, S.H. Goh, and C. Cortez J. Am. Chem. Soc. 97 1975 3468
36. P.P. Fu, R.G. Harvey, and F.A. Beland Tetrahedron 34 1978 857 866
37. A. Maraş, H. Seçen, Y. Sütbeyaz, and M. Balci Turk. J. Chem. 20 1996 341 344