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Synthesis 2001(10): 1459-1461
DOI: 10.1055/s-2001-16096
DOI: 10.1055/s-2001-16096
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis and Characterization of Model Ultimate Carcinogens/Metabolites Derived from Lead Tetraacetate Oxidation of Arylnitrones: 2′-Deoxyguanosine Adducts
Weitere Informationen
Received
9 March 2001
Publikationsdatum:
29. September 2004 (online)
Publikationsverlauf
Publikationsdatum:
29. September 2004 (online)
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Abstract
The synthesis of model reactive metabolites 4a-c by lead tetraacetate (LTA) oxidation of arylnitrones 3a-c is described. Compounds 4a-c react with deoxyguanosine (dG) to give N-benzoylated C8-adducts 5a-c. Following debenzoylation with the heterogeneous system (sodium carbonate/methanol) leads to the corresponding C8-adducts 6a-c.
Key words
model ultimate carcinogens - reactive metabolites - LTA oxidation - arylnitrones - debenzoylation - 2"-deoxyguanosine adducts
-
1a
Bartsch H.Dworkin M.Miller JA.Miller EC. Biochim. Biophys. Acta. 1972, 286: 272 -
1b
Miller EC.Sandin RB.Miller JA.Rusch HP. Cancer Res. 1956, 16: 525 -
1c
Bouck N.Demayorca G. Nature 1976, 264: 722 -
1d
Brookers P.Lawley PD. Nature 1964, 202: 781 -
1e
American Chemical Society Monograph
No. 173:
Clayson DB.Garner RC.Searle CE. ACS; Washington: 1976. p.366 -
f
Heidelberger C. Ann. Rev. Biochem. 1975, 44: 79 -
1g
Kadlubar FF.Miller JA.Miller EC. Cancer Res. 1977, 37: 805 -
1h
Kinosita R. Gann. 1936, 30: 423 -
1i
Berwald Y.Sachs L. Nature 1963, 200: 1182 - 2
Padwa A. Intermolecular 1,3-Dipolar Cycloaddtions, In Comprehensive Organic Synthesis Vol. 4:Semmelhack MF. Pergamon Press; Oxford: 1991. p.1069 - 3
Butler RN.Scott FL.O"Mahony AF. Chem. Rev. 1973, 73: 93 - 4
Hamer J.Macaluso A. Chem. Rev. 1964, 64: 470 -
5a
Ohta A.Ochai E. Chem. Pharm. Bull. 1962, 10: 1260 -
5b
Ohta A.Ochai E. Chem. Pharm. Bull. 1963, 11: 1586 -
6a
Evans CA. Aldrichim. Acta. 1979, 12: 23 -
6b
Janzen EG. Acc. Chem. Res. 1971, 4: 31 -
7a
Barton DHR.Beaton JM. J. Am. Chem. Soc. 1960, 82: 2641 -
7b
Barton DHR.Beaton JM. J. Am. Chem. Soc. 1961, 83: 4083 -
8a
Demeunynck M.Lhomme M.-F.Mellor JM.Lhomme J. J. Org. Chem. 1989, 54: 399 -
8b
Demeunynck M.Tohme N.Lhomme M.-F.Mellor JM.Lohme J. J. Org. Chem. 1989, 54: 405 -
9a
Novak M.Rangappa KS. J. Org. Chem. 1992, 57: 1285 -
9b
Novak M.Rangappa KS.Manitsas RK. J. Org. Chem. 1993, 58: 7813 -
9c
Novak M.Helmick JS.Oberlies N.Rangappa KS.Clark WM.Swenton JS. J. Org. Chem. 1993, 58: 867 -
10a
Splitter JS.Calvin M. J. Org. Chem. 1958, 23: 651 -
10b
Kamlet MJ.Kaplan LA. J . Org. Chem. 1957, 22: 576 -
10c
Shindo H.Umezawa B. Chem. Pharm. Bull. 1962, 10: 492 - 11
Tamagak S.Oae S. Bull. Chem. Soc. Jpn. 1970, 43: 1573 - 12
Galtin L.Davis JC. J. Am. Chem. Soc. 1962, 84: 1464 - 13
Underwood GR.Price MF.Shapiro R. Carcinogenesis 1988, 9: 1817 - 14
Famulok M.Boche G. Angew. Chem., Int. Ed. Engl. 1989, 28: 468 - 15
Meier C.Boche G. Chem. Ber. 1990, 123: 1699 -
16a
Meier C.Boche G. Tetrahedron Lett. 1990, 31: 1685 -
16b
Meier C.Boche G. Chem. Ber. 1990, 123: 1991 -
16c
Meier C.Boche G. Tetrahedron Lett. 1990, 31: 1693 -
17a
Patrick TB.Schield J.Kirchner DG. J. Org. Chem. 1974, 39: 1758 -
17b
Rondestvedt CS.Johnson TA. Synth. Commun. 1977, 7: 850 -
18a
Wheeler OH.Gore PH. J. Am. Chem. Soc. 1956, 78: 3363 -
18b
Beckmann E. Liebigs Ann. Chem. 1909, 367: 273 - 19
Utzinger GE. Liebigs Ann. Chem. 1944, 556: 50 - 20
Kriek E.Miller JA.Juhl U.Miller EC. Biochemistry 1967, 6: 177