AN IMPROVED SYNTHESIS OF ANTI-BENZO[C]PHENANTHRENE-3,4-DIOL 1,2-EPOXIDE VIA 4-METHOXYBENZO[C]PHENANTHRENE

被引:34
作者
MISRA, B [1 ]
AMIN, S [1 ]
机构
[1] AMER HLTH FDN,DIV CHEM CARCINOGENESIS,VALHALLA,NY 10595
关键词
D O I
10.1021/jo00301a054
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzo[c]phenanthrene (1) is a relatively weak carcino-gen1widely distributed in the environment.2Metabolism of 1 on the benzo ring occurs almost exclusively at the 3,4-position to give trans-benzo[c]phenanthrene-3,4-diol3(2), the precursor to the bay region benzo[c]-phenanthrene-3,4-diol 1,2-epoxides (BcPhDE). BcPhDE exists as a pair of diastereoisomers: syn-BcPhDE (3). © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:4478 / 4480
页数:3
相关论文
共 22 条
  • [1] CHEMICAL CHARACTERIZATION OF DNA ADDUCTS DERIVED FROM THE CONFIGURATIONALLY ISOMERIC BENZO[C]PHENANTHRENE-3,4-DIOL 1,2-EPOXIDES
    AGARWAL, SK
    SAYER, JM
    YEH, HJC
    PANNELL, LK
    HILTON, BD
    PIGOTT, MA
    DIPPLE, A
    YAGI, H
    JERINA, DM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) : 2497 - 2504
  • [2] CHROMATOGRAPHIC CONDITIONS FOR SEPARATION OF P-32-LABELED PHOSPHATES OF MAJOR POLYNUCLEAR AROMATIC HYDROCARBON DEOXYRIBONUCLEOSIDE ADDUCTS
    AMIN, S
    MISRA, B
    DESAI, D
    HUIE, K
    HECHT, SS
    [J]. CARCINOGENESIS, 1989, 10 (10) : 1971 - 1974
  • [3] SELECTION OF COHERENCE-TRANSFER PATHWAYS IN NMR PULSE EXPERIMENTS
    BODENHAUSEN, G
    KOGLER, H
    ERNST, RR
    [J]. JOURNAL OF MAGNETIC RESONANCE, 1984, 58 (03) : 370 - 388
  • [4] PHOTOCYCLISATION OF SOME STILBENE ANALOGUES . SYNTHESIS OF DIBENZO [A,L]PYRENE
    CARRUTHERS, W
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (16): : 1525 - +
  • [5] CROISYDELCEY M, 1979, TETRAHEDRON LETT, P2849
  • [6] METABOLISM OF BENZO[C]PHENANTHRENE BY RAT-LIVER MICROSOMES AND BY A PURIFIED MONOOXYGENASE SYSTEM RECONSTITUTED WITH DIFFERENT ISOZYMES OF CYTOCHROME-P-450
    ITTAH, Y
    THAKKER, DR
    LEVIN, W
    CROISYDELCEY, M
    RYAN, DE
    THOMAS, PE
    CONNEY, AH
    JERINA, DM
    [J]. CHEMICO-BIOLOGICAL INTERACTIONS, 1983, 45 (01) : 15 - 28
  • [7] SYNTHESIS OF MONOFLUOROBENZO[C]PHENANTHRENES
    ITTAH, Y
    JERINA, DM
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1980, 16 (02) : 137 - 144
  • [8] JERINA DM, 1982, BIOL REACT INTERMED, V3, P501
  • [9] LEVIN W, 1980, CANCER RES, V40, P3910
  • [10] LEVIN W, 1986, CANCER RES, V46, P2257