7-硝基-苯并[k]苯并[a]蒽 | 63041-91-8

• 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: 7-硝基-苯并[k]苯并[a]蒽
• 英文名称: 7-nitrodibenzanthracene
• 英文别名: Dibenz(a,h)anthracene, 7-nitro-；14-nitronaphtho[1,2-b]phenanthrene
• CAS: 63041-91-8
• 化学式: C₂₂H₁₃NO₂
• 分子量: 323.351
• InChiKey: ZZMDJBHMGFRFEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2904209090

反应信息

• 作为反应物：
  描述：

  7-硝基-苯并[k]苯并[a]蒽 生成 萘并[1,2-b]菲-7,14-二酮
  参考文献：
  名称：

  JOHANSEN, HEGE;DOEL, JO;GREIBROKK, TYGE, RAPORTTISAR. MAT.-LUONNONTICTEELLIS. TIEDEKUNNAN ,(1989) N9, C. 24-27

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯并[a,h]蒽 在 硝酸 、 溶剂黄146 作用下， 生成 7-硝基-苯并[k]苯并[a]蒽
  参考文献：
  名称：

  ProzLIV.-多环芳烃。第八部分。1：2：5：6-二苯并蒽的化学反应

  摘要：

  DOI：

  10.1039/jr9310003273

文献信息

• Iversen, Berit; Sydnes, Leiv K.; Greibrokk, Tyge, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 10, p. 837 - 848
  作者：Iversen, Berit、Sydnes, Leiv K.、Greibrokk, Tyge

  DOI：——

  日期：——
• Structure, Tumorigenicity, Microsomal Metabolism, and DNA Binding of 7-Nitrodibenz[<i>a,h</i>]anthracene
  作者：Peter P. Fu、Linda S. Von Tungeln、Li-Hsueh Chiu、De-Jin Zhan、Joanna Deck、Thomas Bucci、Ju-Chun Wang

  DOI：10.1021/tx980079+

  日期：1998.8.1

  It has been previously proposed that a nitropolycyclic aromatic hydrocarbon (nitro-PAH) with its nitro functional group perpendicular or nearly perpendicular to the aromatic moiety exhibits lower tumorigenicity than the corresponding parent aromatic hydrocarbon. We also hypothesized that reduction of the nitro group is not involved, or contributed less significantly in the metabolic activation of this class of nitro-PAHs. To verify this hypothesis, we selected 7-nitrodibenz[a,h]anthracene (7-NDB[a,h]A) for study. The X-ray crystallographic structure of 7-NDB[a,h]A was determined and indicated that the dihedral angle between the nitro functional group and the aromatic dibenz[a,h]anthracenyl moiety was 80.6 degrees, indicating the nitro group preferentially adopts a nearly perpendicular orientation. The tumorigenicity of 7-NDB[a,h]A and dibenz[a,h]anthracene (DB[a,h]A) was determined in the male B6C3F(1) neonatal mouse. Mice were administered ip injections of 1/7, 2/7, and 4/7 of the total dose of 7-NDB[a,h]A (400 nmol in 35 mu L of DMSO per mouse) within 24 h of birth and at 8 and 15 days of age, respectively, and sacrificed at 12 months of age. DB[a,h]A induced 78 and 96% hepatocellular adenomas and carcinomas, respectively. However, 7-NDB[a,h]A induced only 50 and 8% hepatocellular adenomas and carcinomas compared with the 8 and 4% hepatocellular adenomas and carcinomas induced by the solvent vehicle, DMSO. Aerobic metabolism of 7-NDB[a,h]A by liver microsomes of 15-day old male B6C3F(1) neonatal mice resulted in trans-3,4-dihydroxy-3,4-dihydro-7-nitrodibenz[a,h]anthracene (7-NDB[a,h]A trans-3,4-dihydrodiol) and trans-10,11-dihydroxy-10,11-dihydro-7-nitrodibenz[a,h]anthracene (7-NDB[a,h]A trans-10,11-dihydrodiol) as predominant metabolites. Under anaerobic conditions, 7-NDB[a,h]A was not metabolized (nitroreduced). The DNA adduct levels in liver and lung tissues of male B6C3F1 mice treated with 7-NDB[a,h]A and sacrificed 24 h and 6 days after final dosing were determined by P-32-postlabeling/TLC. In all cases, the DNA adducts derived from 7-NDB[a,h]A trans-3,4-dihydrodiol and 7-NDB[a,h]A trans-10,11-dihydrodiol were formed. These results suggest that both of the metabolites, 7-NDB[a, h]A trans-3,4-dihydrodiol and 7-NDB[a,h]A trans-10,11-dihydrodiol, are involved in the metabolic activation of 7-NDB[a,h]A, leading to tumor induction in the neonatal mouse. Thus, our results described in this paper support our hypotheses that a nitro-PAH with a perpendicular nitro orientation exhibits lower tumorigenicity than the corresponding parent PAH and that nitroreduction contributes less significantly in the metabolic activation.