메뉴 건너뛰기




Volumn 29, Issue 5, 2009, Pages 282-288

A facile synthesis of 11,12-dimethoxydibenzo[def,p]chrysene, a preferred precursor for the synthesis of the proximate and ultimate carcinogens of dibenzo[def,p]chrysene (DBC)

Author keywords

Carcinogenesis; Dibenzo def,p chrysene; Polycyclic aromatic hydrocarbons; Suzuki cross coupling reaction

Indexed keywords

CARCINOGENS; CHEMICAL REACTIONS; POTASSIUM COMPOUNDS;

EID: 72149115397     PISSN: 10406638     EISSN: 15635333     Source Type: Journal    
DOI: 10.1080/10406630903299561     Document Type: Article
Times cited : (3)

References (21)
  • 1
    • 0015447058 scopus 로고
    • A novel synthesis and carcinogenicity of dibenzo[a,l]pyrene
    • Masuda, Y., and R. Kagawa. 1972. A novel synthesis and carcinogenicity of dibenzo[a,l]pyrene. Chem. Pharm. Bull. 20:2736-2737.
    • (1972) Chem. Pharm. Bull. , vol.20 , pp. 2736-2737
    • Masuda, Y.1    Kagawa, R.2
  • 2
    • 0027159541 scopus 로고
    • Tumor-initiating activity and carcinogenicity of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene at low doses in mouse skin
    • Higginbotham, S., N. V. S. RamaKrishna, S. L. Johansson, E. G. Rogan, and E. L. Cavalieri. 1993. Tumor-initiating activity and carcinogenicity of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene at low doses in mouse skin. Carcinogenesis (Lond.) 14: 875-878.
    • (1993) Carcinogenesis (lond.) , vol.14 , pp. 875-878
    • Higginbotham, S.1    Ramakrishna, N.V.S.2    Johansson, S.L.3    Rogan, E.G.4    Cavalieri, E.L.5
  • 3
    • 0027328275 scopus 로고
    • Exceptional tumor-initiating activity of 4-fluorobenzo[j]fluoranthene on mouse skin: Compar- ison with benzo[j]fluoranthene, 10-fluoro-benzo[j]fluoranthene, benzo[a]pyrene, dibenzo[a,l]pyrene and 7,12-dimethylbenz[a]anthracene
    • LaVoie, E. J., Z.-M. He, R. L. Meegalla, and E. H. Weyand, 1993. Exceptional tumor-initiating activity of 4-fluorobenzo[j]fluoranthene on mouse skin: compar- ison with benzo[j]fluoranthene, 10-fluoro-benzo[j]fluoranthene, benzo[a]pyrene, dibenzo[a,l]pyrene and 7,12-dimethylbenz[a]anthracene. Cancer Lett. 70:7-14.
    • (1993) Cancer Lett. , vol.70 , pp. 7-14
    • Lavoie, E.J.1    He, Z.-M.2    Meegalla, R.L.3    Weyand, E.H.4
  • 4
    • 0026002897 scopus 로고
    • Comparative dose-response tumori- genicity studies of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene, benzo[a]pyrene and two dibenzo[a,l]pyrene dihydrodiols in mouse skin and rat mammary gland
    • Cavalieri, E. L., S. Higginbotham, N. V. S. RamaKrishna, P. D. Devanesan, R. Todorovic, E. G. Rogan, and S. Salmasi. 1991. Comparative dose-response tumori- genicity studies of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene, benzo[a]pyrene and two dibenzo[a,l]pyrene dihydrodiols in mouse skin and rat mammary gland. Carcinogenesis (Lond.). 12:1939-1944.
    • (1991) Carcinogenesis (lond.) , vol.12 , pp. 1939-1944
    • Cavalieri, E.L.1    Higginbotham, S.2    Ramakrishna, N.V.S.3    Devanesan, P.D.4    Todorovic, R.5    Rogan, E.G.6    Salmasi, S.7
  • 5
    • 84941386774 scopus 로고
    • The identification of high molecular weight polynuclear aromatic hydrocarbons in a biologically active fraction of cigarette smoke condensate
    • Snook, M. E., Severson, R. F., Arrendale, R. F., Higman, H. C., and Chortyk, O. T. 1977. The identification of high molecular weight polynuclear aromatic hydrocarbons in a biologically active fraction of cigarette smoke condensate. Beitr. Tabakforsch. 9:79-101.
    • (1977) Beitr. Tabakforsch , vol.9 , pp. 79-101
    • Snook, M.E.1    Severson, R.F.2    Arrendale, R.F.3    Higman, H.C.4    Chortyk, O.T.5
  • 6
    • 0023305989 scopus 로고
    • Indoor air sampling and mutagenicity studies of emissions from unvented coal combustion
    • Mumford, J. L., D. B. Harris, K. Williams, J. C. Chuang, and M. Cooke. 1987. Indoor air sampling and mutagenicity studies of emissions from unvented coal combustion. Environ. Sci. Technol. 21:308-311.
    • (1987) Environ. Sci. Technol , vol.21 , pp. 308-311
    • Mumford, J.L.1    Harris, D.B.2    Williams, K.3    Chuang, J.C.4    Cooke, M.5
  • 7
    • 0023522958 scopus 로고
    • Concentrations of polycyclic hydrocarbons in airborne particles in Netherlands and their correlation with mutagenicity
    • DeRatt, W. K., S. A. L. M. Kooijman, and J. W. J. Gielen.1987. Concentrations of polycyclic hydrocarbons in airborne particles in Netherlands and their correlation with mutagenicity. Sci. Technol. Environ. 66: 95-114.
    • (1987) Sci. Technol. Environ , vol.66 , pp. 95-114
    • Deratt, W.K.1    Kooijman, S.A.L.M.2    Gielen, J.W.J.3
  • 8
    • 0000815212 scopus 로고
    • Direct determination of dibenzo[a,l]pyrene in crude extracts of environmental samples by laser excited Shpol'skii spectroscopy
    • Kozin, I. S., C. Gooijer, and N. H. Velthorst. 1995. Direct determination of dibenzo[a,l]pyrene in crude extracts of environmental samples by laser excited Shpol'skii spectroscopy. Anal. Chem. 67:1623-1626.
    • (1995) Anal. Chem. , vol.67 , pp. 1623-1626
    • Kozin, I.S.1    Gooijer, C.2    Velthorst, N.H.3
  • 9
    • 0028268392 scopus 로고
    • The potent carcinogen dibenzo[a,l]pyrene is metabolically activated to fjord-region 11,12-diol 13,14-epoxide in human mammary carcinoma MCF-7 cell cultures
    • Ralston, S. L., H. H. S. Lau, A. Seidel, A. Luch, K. L. Platt, and W. M. Baird. 1994. The potent carcinogen dibenzo[a,l]pyrene is metabolically activated to fjord-region 11,12-diol 13,14-epoxide in human mammary carcinoma MCF-7 cell cultures. Cancer Res. 54:887-890.
    • (1994) Cancer Res. , vol.54 , pp. 887-890
    • Ralston, S.L.1    Lau, H.H.S.2    Seidel, A.3    Luch, A.4    Platt, K.L.5    Baird, W.M.6
  • 10
    • 0028061909 scopus 로고
    • Synthesis and mutagenicity of the diastereomeric fjord-region 11,12-dihydrodiol 13,14-epoxides of dibenzo[a,l]pyrene
    • Luch, A., H. Glatt, K. L. Platt, F. Oesch, and A. Seidel. 1994. Synthesis and mutagenicity of the diastereomeric fjord-region 11,12-dihydrodiol 13,14-epoxides of dibenzo[a,l]pyrene. Carcinogenesis (Lond.). 15:2507-2516.
    • (1994) Carcinogenesis (lond.) , vol.15 , pp. 2507-2516
    • Luch, A.1    Glatt, H.2    Platt, K.L.3    Oesch, F.4    Seidel, A.5
  • 11
    • 0028887082 scopus 로고
    • Tumorigenicity in newborn mice of fjord region and other sterically hindered diol epoxides of benzo[g]chrysene, dibenzo[a,l]pyrene (dibenzo[def,p]chrysene), 4H-cyclopenta[def]chrysene and fluoranthene
    • Amin, S., D. Desai, W. Dai, R. G. Harvey, and S. S. Hecht. 1995. Tumorigenicity in newborn mice of fjord region and other sterically hindered diol epoxides of benzo[g]chrysene, dibenzo[a,l]pyrene (dibenzo[def,p]chrysene), 4H-cyclopenta[def]chrysene and fluoranthene. Carcinogenesis (Lond.). 16:2813-2817.
    • (1995) Carcinogenesis (lond.) , vol.16 , pp. 2813-2817
    • Amin, S.1    Desai, D.2    Dai, W.3    Harvey, R.G.4    Hecht, S.S.5
  • 12
    • 0029142955 scopus 로고
    • Mammary carcinogenicity in female CD rats of fjord region diol epoxides of benzo[c]phenanthrene, benzo[g]chrysene and dibenzo[a,l]pyrene
    • Amin, S., J. Krzeminski, A. Rivenson, C. Kurtzke, S. S. Hecht, and K. El-Bayoumy. 1995. Mammary carcinogenicity in female CD rats of fjord region diol epoxides of benzo[c]phenanthrene, benzo[g]chrysene and dibenzo[a,l]pyrene. Carcinogenesis (Lond.). 16:1971-1974.
    • (1995) Carcinogenesis (lond.) , vol.16 , pp. 1971-1974
    • Amin, S.1    Krzeminski, J.2    Rivenson, A.3    Kurtzke, C.4    Hecht, S.S.5    El-Bayoumy, K.6
  • 13
    • 0027959934 scopus 로고
    • Synthesis and tumor-initiating activity in mouse skin of dibenzo[a,l]pyrene syn- and anti-fjord-region diolepoxides
    • Gill, H. S., P. L. Kole, J. C. Wiley, K.-M. Li, S. Higginbotham, E. G. Rogan, E. L. Cavalieri. 1994. Synthesis and tumor-initiating activity in mouse skin of dibenzo[a,l]pyrene syn- and anti-fjord-region diolepoxides. Carcinogenesis (Lond.). 15:2455-2460.
    • (1994) Carcinogenesis (lond.) , vol.15 , pp. 2455-2460
    • Gill, H.S.1    Kole, P.L.2    Wiley, J.C.3    Li, K.-M.4    Higginbotham, S.5    Rogan, E.G.6    Cavalieri, E.L.7
  • 14
    • 0031041812 scopus 로고    scopus 로고
    • NMR solution structures of stereomeric covalent polycyclic aromatic carcinogen-DNA adducts: Principle, pattern and diversity
    • Geacintov, N. E., M. Cosman, B. E. Hingerty, S. Amin, S. Broyde, and D. J. Patel. 1997. NMR solution structures of stereomeric covalent polycyclic aromatic carcinogen-DNA adducts: Principle, pattern and diversity. Chem. Res. Toxicol. 10:111-146.
    • (1997) Chem. Res. Toxicol , vol.10 , pp. 111-146
    • Geacintov, N.E.1    Cosman, M.2    Hingerty, B.E.3    Amin, S.4    Broyde, S.5    Patel, D.J.6
  • 15
    • 0028707724 scopus 로고
    • IARC Scientific Publication No. 125; Hemminki, K., A. Dipple, D. E. G. Shuker, F. F. Kadlubar, D. Segerback, H. Bartsch, Eds. International Agency for Research on Cancer: Lyon, France
    • Dipple, A. 1994. DNA Adducts: Identification and Biological Significance; IARC Scientific Publication No. 125; Hemminki, K., A. Dipple, D. E. G. Shuker, F. F. Kadlubar, D. Segerback, H. Bartsch, Eds. International Agency for Research on Cancer: Lyon, France. pp 107-129.
    • (1994) Dna Adducts: Identification and Biological Significance , pp. 107-129
    • Dipple, A.1
  • 16
    • 2442665320 scopus 로고    scopus 로고
    • A highly abbreviate synthesis of dibenzo[def,p]chrysene and its 12-methoxy derivative, a key precursor for the synthesis of the proximate and ultimate carcinogens of dibenzo[def,p]chrysene
    • Sharma, A. K., S. Kumar, and S. Amin. 2004. A highly abbreviate synthesis of dibenzo[def,p]chrysene and its 12-methoxy derivative, a key precursor for the synthesis of the proximate and ultimate carcinogens of dibenzo[def,p]chrysene. J. Org. Chem. 69:3979.
    • (2004) J. Org. Chem. , vol.69 , pp. 3979
    • Sharma, A.K.1    Kumar, S.2    Amin, S.3
  • 17
    • 0033555382 scopus 로고    scopus 로고
    • Syntheses of oxidized metabolites implicated as active forms of the highly potent carcinogenic hydrocarbon dibenzo[def,p]chrysene
    • Zhang, J.-T., and R. G. Harvey. 1999. Syntheses of oxidized metabolites implicated as active forms of the highly potent carcinogenic hydrocarbon dibenzo[def,p]chrysene. Tetrahedron. 55:625-636.
    • (1999) Tetrahedron , vol.55 , pp. 625-636
    • Zhang, J.-T.1    Harvey, R.G.2
  • 18
    • 0032514452 scopus 로고    scopus 로고
    • A versatile synthesis of fully aromatic benzo[c]phenanthridine alkaloids
    • Geen, G. R., I. S. Mann, and M. V. Mullane. 1998. A versatile synthesis of fully aromatic benzo[c]phenanthridine alkaloids. Tetrahedron. 54:9875-9894.
    • (1998) Tetrahedron , vol.54 , pp. 9875-9894
    • Geen, G.R.1    Mann, I.S.2    Mullane, M.V.3
  • 21
    • 33947092250 scopus 로고
    • Abnormal products in the Siegrist recation involving ortho-fluorinated intermediates
    • Newman, M. S., B. Dhawan, and S. Kumar. 1976. Abnormal products in the Siegrist recation involving ortho-fluorinated intermediates. J. Org. Chem. 41:524-525.
    • (1976) J. Org. Chem. , vol.41 , pp. 524-525
    • Newman, M.S.1    Dhawan, B.2    Kumar, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.