[1S,(-)]-1,2,3,4-四氢-1a,2a-环氧苯并[a]蒽-3b,4a-二醇 | 80433-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: [1S,(-)]-1,2,3,4-四氢-1a,2a-环氧苯并[a]蒽-3b,4a-二醇
• 英文名称: r-3,t-4-dihydroxy-t-1,2-epoxy-1,2,3,4-tetrahydrobenzanthracene
• 英文别名: anti-benz[a]anthracene-trans-3,4-dihydrodiol-1,2-epoxide；rel-(1aR,2S,3R,11cS)-1a,2,3,11c-Tetrahydrotetrapheno[1,2-b]oxirene-2,3-diol；(3S,5R,6S,7R)-4-oxapentacyclo[9.8.0.02,8.03,5.013,18]nonadeca-1(19),2(8),9,11,13,15,17-heptaene-6,7-diol
• CAS: 80433-78-9
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: JNQSJMYLVFOQBK-VSZNYVQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1S,(-)]-1,2,3,4-四氢-1a,2a-环氧苯并[a]蒽-3b,4a-二醇 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 r-1,t-2,3-c-4-tetrahydroxy-1,2,3,4-tetrahydrobenzanthracene
  参考文献：
  名称：

  通过气相色谱-质谱法和-3H-CH3I后标记释放的四醇检测多核芳烃二醇环氧化物的DNA和球蛋白加合物。

  摘要：

  气相色谱-负离子化学电离质谱法-选择性离子监控（GC-NICI-MS-SIM）用于检测DNA水解形成的四醇的四甲醚衍生物和衍生自苯并[a]-的二醇环氧化物的球蛋白加合物BP（BP）和其他多核芳香烃（PAH）。四甲基醚衍生物也可以通过[3H] CH3I后标记进行检测。该方法包括以下步骤：（1）分离DNA或球蛋白；（2）在真空下温和的酸水解；（3）分离得到的四醇，并使用甲基亚磺酰基碳负离子和未标记的或3H标记的CH 3 I衍生化为相应的四甲基醚；（4）通过GC-NICI-MS-SIM或具有无线电流检测功能的HPLC分析。探索了加合物水解和所得四醇衍生化的最佳条件，以及这种方法在小鼠和人类中检测PAH加合物的可行性。使用可以在水解由r-7，t-8-二羟基-t-9,10-环氧-7,8,9,10-四氢苯并[a] formed（抗BPDE）或r-7，t-8-二羟基-c-9,10-环氧-7,8,9,10-四氢苯并[a]

  DOI：

  10.1021/tx950165z
• 作为产物：
  描述：

  (1S,2R,3S,4R)-2-bromo-1,2,3,4-tetrahydrobenzo[a]anthracene-1,3,4-triol 以85%的产率得到
  参考文献：
  名称：

  YAGI, HARUHIKO;VYAS, KAMLESH, P.;TADA, MASAO;THAKKER, D. R.;JERINA, D. M., J. ORG. CHEM., 1982, 47, N 6, 1110-1117

  摘要：

  DOI：

文献信息

• Conformational effects in the hydrolyses of benzo-ring diol epoxides that have bay-region diol groups
  作者：J. M. Sayer、D. L. Whalen、S. L. Friedman、A. Paik、H. Yagi、K. P. Vyas、D. M. Jerina

  DOI：10.1021/ja00313a044

  日期：1984.1

  Etude realisee sur des diol epoxydes des benzo [a] anthracene, triphenylene et benzo [e] pyrene dans lesquels les equilibres entre les conformations alignees et non alignees sont modifies par la localisation du groupe diol dans une region baie de la molecule

  Etude realisee sur des diolepoxydes benzo [a] anthracene, triphenylene et benzo [e] pyrene dans lesquels les equilibres entre les 构象 alignees et non alignees sont 修改 par la localization du groupe diol dans une region baie de la 分子
• Synthesis of the enantiomeric bay-region diol epoxides of benz[a]anthracene and chrysene
  作者：Haruhiko Yagi、Kamlesh P. Vyas、Masao Tada、Dhiren R. Thakker、Donald M. Jerina

  DOI：10.1021/jo00345a043

  日期：1982.3
• Structures of covalent nucleoside adducts formed from adenine, guanine, and cytosine bases of DNA and the optically active bay-region 3,4-diol 1,2-epoxides of benz[a]anthracene
  作者：Albert M. Cheh、Anju Chadha、Jane M. Sayer、Herman J. C. Yeh、Haruhiko Yagi、Lewis K. Pannell、Donald M. Jerina

  DOI：10.1021/jo00067a039

  日期：1993.7

  Chemical structures of the principal covalent adducts formed from DNA upon reaction in vitro with the four optically active 3,4-diol 1,2-epoxides of benz[a]anthracene have been elucidated at the nucleoside level. In addition to adducts formed by cis and trans addition of the exocyclic amino groups of deoxyadenosine (dA) and deoxyguanosine (dG) and a trans deoxycytidine (dC) adduct, chemical characterization of a deglycosylated N-7 dG adduct formed in DNA by trans opening of the (4S,3R)-diol (2R,1S)-epoxide isomer is reported. Relative stereochemistries of the adducts (cis versus trans opening of the epoxides by the exocyclic amino groups) were deduced from the coupling constants of the methine protons of the tetrahydro benzo rings of the acetylated derivatives. Adducts having (S)-configuration at the attachment site on the hydrocarbon moiety have CD spectra that exhibit a positive band at 250-260 nm and a negative band at longer wavelengths, whereas (R)-configuration at this center gives rise to CD spectra with bands of approximately equal intensity and opposite sign. This allowed assignment of cis versus trans addition to the chiral epoxides for adducts that were not generated in sufficient quantity to obtain NMR spectra. Analysis of the patterns of adducts derived from benz[a]anthracene, benzo[c]phenanthrene, and benzo[a]pyrene shows that the comparative tumorigenicities of the diol epoxide isomers of each hydrocarbon do not correlate well with the extent of adduct formation, the ratio of cis versus trans addition to the epoxide, the propensity for forming adducts at dC or the N-7 position of dG, or the ratio of adduct formation at dA versus dG, although tumorigenicity may correlate with the ability to form dG adducts with (S)-configuration at the N-substituted benzylic carbon, especially those arising from trans addition to the epoxide.