EFFICIENT NEW SYNTHESES OF POLYCYCLIC AROMATIC HYDROCARBON ORTHO-QUINONES AND THEIR 2′-DEOXYRIBONUCLEOSIDE ADDUCTS

REFERENCES

• Harvey , R. G. 1991 . Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity , Cambridge : Cambridge University Press .
   Google Scholar
• Dipple , A. , Moschel , R. C. and Bigger , C. A. H. 1985 . “ Polynuclear Aromatic Carcinogens ” . In Chemical Carcinogenesis , 41 – 163 . Washington, D.C. : American Chemical Society . in
   Google Scholar
• Conney , A. H. 1982 . Induction of Microsomal Enzymes by Foreign Chemicals and Carcinogenesis by Polycyclic Aromatic Hydrocarbons . Cancer Res. , 42 : 4875 – 4917 .
   PubMed Web of Science ®Google Scholar
• Dipple , A. 1994 . “ Reactions of Polycyclic Aromatic Hydrocarbons with DNA ” . In DNA Adducts: Identification and Biological Significance , Edited by: Hemminki , K. 107 – 129 . Lyon : International Agency for Research on Cancer . IARC Scientific Publication no. 125
   Google Scholar
• Jeffrey , A. M. , Weinstein , I. B. , Jennette , K. , Grzeskowiak , K. , Nakanishi , K. , Harvey , R. G. , Autrup , H. and Harris , C. 1977 . Structures of Benzo[a]pyrene-Nucleic Acid Adducts Formed in Human and Bovine Bronchial Explants . Nature (London). , 269 : 348 – 350 .
   PubMed Web of Science ®Google Scholar
• Jennette , K. , Jeffrey , A. M. , Blobstein , S. H. , Beland , F. A. , Harvey , R. G. and Weinstein , I. B. 1977 . Characterization of Nucleoside Adducts from the In Vitro Reaction of Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide or Benzo[a]pyrene-4,5-oxide with Nucleic Acids . Biochemistry , 16 : 932 – 938 .
   PubMed Web of Science ®Google Scholar
• Smithgall , T. E. , Harvey , R. G. and Penning , T. M. 1986 . Regio- and Stereospecificity of Homogeneous 3d-hydroxysteriod-dehydrodiol Dehydrogenase for transDihydrodiol Metabolites of Polycyclic Aromatic Hydrocarbons . J. Biol. Chem. , 261 : 6184 – 6191 .
   PubMed Web of Science ®Google Scholar
• 1988 . Ibid. Oxidation of the trans-3,4-Dihydrodiol Metabolites of the Potent Carcinogen 7,12-Dimethylbenz[a]anthracene and Other Benz[a]anthracene Derivatives by 3a-Hydroxysteroid-Dihydrodiol Dehydrogenase: Effects of Methyl Substitution on Velocity and Stereochemical Course of trans-Dihydrodiol Oxidation . Cancer Res. , 48 : 1227 – 1232 .
   PubMed Web of Science ®Google Scholar
• 1988 . Ibid. Spectroscopic Identification of ortho-Quinones as the Products of Polycyclic Aromatic trans-Dihydrodiol Oxidation Catalyzed by Dihydrodiol Dehydrogenase: A Potential Route of Proximate Carcinogen Metabolism . J. Biol. Chem. , 263 : 1814 – 1820 .
   PubMed Web of Science ®Google Scholar
• Shou , M. , Harvey , R. G. and Penning , T. M. 1993 . Reactivity of Benzo[a]pyrene-7,8-dione with DNA: Evidence for the Formation of Deoxyguanosine Adducts . Carcinogenesis , 14 : 475 – 482 .
   PubMed Web of Science ®Google Scholar
• McCoull , K. D. , Rindgen , D. , Blair , I. A. and Penning , T. M. 1999 . Synthesis and Characterization of Polycyclic Aromatic Hydrocarbon o-Quinone Depurinating N7-Guanine Adducts . Chem. Res. Toxicol. , 12 : 237 – 246 .
   PubMed Web of Science ®Google Scholar
• Cavalieri , E. L. and Rogan , E. G. 1995 . Central Role of Radical Cations in Metabolic Activation of Polycyclic Aromatic Hydrocarbons . Xenobiotica , 25 : 677 – 688 .
   PubMed Web of Science ®Google Scholar
• Melendez-Colon , V. , Luch , A. , Seidel , A. and Baird , W. 1999 . Cancer Initiation by Polycyclic Aromatic Hydrocarbons Results from Formation of Stable DNA Adducts Rather than Apurinic Sites . Carcinogenesis , 20 : 1885 – 1891 . The role of the radical-cation pathway is controversial
   PubMed Web of Science ®Google Scholar
• Zhang , F.-J. , Cortez , C. and Harvey , R. G. 2000 . New Synthetic Approaches to Polycyclic Aromatic Hydrocarbons and Their Carcinogenic Oxidized Metabolites: Derivatives of Benzo[s]picene, Benzo[rst]pentaphene, and Dibenz[b,def]chrysene . J. Org. Chem. , 65 : 3952 – 3960 .
   PubMedGoogle Scholar
• Kumar , S. 2001 . Synthesis of trans-3,4-Dihydroxy-3,4- dihydrophenanthro[3,2-b]-[1] benzothiophene, a Potentially Carcinogenic Metabolite of Sulfur Heterocyclic Phenanthro[3,2-b]benzothiophene . J. Chem. Soc. Perkin Trans. , 1 : 1018 – 1023 .
   Google Scholar
• Mataka , S. , Liu , G.-B. , Sawada , T. , Kurisu , M. and Tashiro , M. 1994 . Photothermal Side-Chain Bromination of Methyl-, Dimethyl-, and Trimethylbenzenes with NBromosuccinimide . Bull. Chem. Soc. Jpn. , 67 : 1113 – 1119 .
   Google Scholar
• Makasza , M. and Owczarczyk , Z. 1989 . Dihaloarylation of Nitroarenes via Vicarious Nucleophilic Substitution of Hydrogen with Trihalomethyl Carbanions . J. Org. Chem. , 54 : 5094 – 5100 .
   Google Scholar
• Mataka , S. , Liu , G.-B. , Sawada , T. , Tori-I , A. and Tashiro , M. 1995 . Preparation of Benzene-1,3-dicarbaldehyde . J. Chem. Res. (Synopses) , : 410 – 411 .
   Google Scholar
• Mallory , F. B. and Mallory , C. W. 1988 . Photocyclization of Stilbenes and Related Molecules . Org. Reactions , 30 : 1 – 456 .
   Google Scholar
• Sukumaran , K. B. and Harvey , R. G. 1980 . Synthesis of o-Quinones and Dihydrodiols of Polycyclic Aromatic Hydrocarbons from the Corresponding Phenols . J. Org. Chem. , 45 : 4407 – 4413 .
   Web of Science ®Google Scholar
• Zimmer , H. , Lankin , D. C. and Horgan , S. W. 1971 . Oxidation with Potassium Nitrosodisulfonate (Fremy's radical): Teuber Reaction . Chem. Rev. , 71 : 229 – 246 .
   Web of Science ®Google Scholar
• Nicolaou , K. C. , Montagnon , T. , Baran , P. S. and Zhong , Y.-L. 2002 . Iodine (V) Reagents in Organic Synthesis: IV. o-Iodoxybenzoic Acid as a Chemospecific Tool for Single Electron Transfer-Based Oxidation Processes . J. Am. Chem. Soc. , 124 : 2245 – 2258 .
   PubMed Web of Science ®Google Scholar
• Magdziak , D. , Rodriguez , A. A. , Van De Water , R. W. and Pettus , T. R. R. 2001 . Regioselective Oxidation of Phenols to o-Quinones with o-Iodoxybenzoic Acid (IBX) . Org. Lett. , 4 : 284 – 288 .
   Google Scholar
• Sharma , P. K. 1993 . A New Synthesis of trans-3,4-Dihydroxy-anti-1,2-epoxy-1,2,3,4- tetrahydro-7,12-dimethylbenz(a)anthracene . Syn. Commun. , 23 : 389 – 394 .
   Web of Science ®Google Scholar
• Sharma , A. K. , Amin , S. and Kumar . 2002 . An Abbreviated Synthesis of 7,12-Dimethylbenz[a]anthracene and Benzo[c]chrysene Metabolites Using the Suzuki Reaction . Polycyclic Arom. Compds. , 22 : 277 – 288 .
   Web of Science ®Google Scholar
• Washburn , R. M. , Levens , E. , Albright , C. F. and Billig , F. A. 1963 . Benzeneboronic Anhydride . Org. Syn., coll. , vol. 4 : 68 – 72 .
   Google Scholar
• Harmata , M. and Kahraman , M. 1999 . Preparation of 2,8-Dihydroxy 5,6,11,12- tetrahydro 5,11-epoxydibenzo[a,e]cycloctene, an Analogue of Kagan's Ether . J. Org. Chem. , 64 : 4949 – 4952 .
   PubMedGoogle Scholar
• Léo , P.-M. , Morin , C. and Philouze , C. 2002 . Structure Revision of Medermycin/Lactoquinomycin A and of Related C-8 Glycosylated Naphthoquinones . Org. Lett. , 4 : 2711 – 2714 .
   PubMed Web of Science ®Google Scholar
• Kumar , S. 1998 . A New Efficient Route to the Phenolic Derivatives of Chrysene and 5-Methylchrysene, Precursors to Dihydrodiol and Diol Epoxide Methabolites of Chrysene and 5-Methylchrysene, Through Suzuki Cross-Coupling Reaction . J. Chem. Soc. Perkin Trans. , 1 : 3157 – 3162 .
   Google Scholar
• Lee , H. and Harvey , R. G. 1986 . Synthesis of the Active Diol Epoxide Metabolites of the Potent Carcinogenic Hydrocarbon 7,12-Dimethylbenz[a]anthracene . J. Org. Chem. , 51 : 3502 – 3507 .
   Google Scholar
• Newman , M. S. , Khanna , J. M. , Khanna , V. K. and Kanakarajan , K. 1979 . Syntheses of 7,12-Dimethylbenz[a]anthracene-3,4 and 1,4-diones . J. Org. Chem. , 44 : 4994 – 4995 .
   Web of Science ®Google Scholar
• Konieczny , M. and Harvey , R. G. 1979 . Efficient Reduction of Polycyclic Quinones, Hydroquinones, and Phenols to Polycyclic Aromatic Hydrocarbons with Hydroiodic Acid . J. Org. Chem. , 44 : 4813 – 4816 .
   Web of Science ®Google Scholar
• Harvey , R. G. 1997 . Polycyclic Aromatic Hydrocarbons , New York : Wiley-VCH .
   Google Scholar
• Cho , H. and Harvey , R. G. 1976 . Synthesis of Hydroquinone Diacetates from Polycyclic Aromatic Quinones . J. Chem. Soc. Perkin Trans. , 1 : 836 – 839 .
   Google Scholar
• Husu , B. , Kafka , S. , Kadunc , Z. and Tisler , M. 1988 . Amination of Naphthoquinones with Azidotrimethylsilane . Monat. Chem. , 119 : 215 – 222 .
   Google Scholar
• Wolfe , J. P. , Tomori , H. , Sadighi , J. P. , Yin , J. and Buchwald , S. L. 2000 . Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates . J. Org. Chem. , 65 : 1158 – 1174 .
   PubMed Web of Science ®Google Scholar