1,2-二氢-1,2-二羟基-6-硝基屈 | 91828-72-7

• 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: 1,2-二氢-1,2-二羟基-6-硝基屈
• 英文名称: trans-1,2-dihydroxy-1,2-dihydro-6-nitrochrysene
• 英文别名: 1,2-Dihydro-1,2-dihydroxy-6-nitrochrysene；(1S,2S)-6-nitro-1,2-dihydrochrysene-1,2-diol
• CAS: 91828-72-7
• 化学式: C₁₈H₁₃NO₄
• 分子量: 307.306
• InChiKey: LZFRXTYVXJWZHG-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-二氢-1,2-二羟基-6-硝基屈 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以76%的产率得到anti-1,2-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydro-6-nitrochrysene
  参考文献：
  名称：

  Synthesis of anti-1,2-Dihydroxy-3,4-epoxy-1,2,3,4-tetrahydro-6-nitrochrysene and Its Reaction with 2‘-Deoxyguanosine- 5‘-Monophosphate, 2‘-Deoxyadenosine-5‘-Monophosphate, and Calf Thymus DNA in Vitro

  摘要：

  The remarkable carcinogenic activity of 6-nitrochrysene (6-NC) in several animal models, and its environmental presence, suggest its potential importance with regard to human cancer development. Depending on the bioassay model, 6-NC can be activated by simple nitro reduction, ring oxidation, or by a combination of ring oxidation and nitro reduction. Only the first pathway has been clearly established. Thus, this study purports to unequivocally define the other pathways. Toward this end, we report for the first time the synthesis of anti-1,2-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydro-6-nitrochrysene (6-NCDE), a likely ultimate carcinogenic metabolite of 6-NC. Also, we describe our initial investigation of its binding with calf thymus DNA, 2'-deoxyguanosine-5'-monophosphate (2'-dGuo), and 2'-deoxyadenosine-5'-monophosphate (2'-dAdo) in vitro. These adduct markers were then employed for comparison with those obtained in the rat after in vivo treatment with 6-NC. On the basis of the results, it appears that the major adduct formed in the liver of rats treated with 6-NC is not derived from 6-NCDE.

  DOI：

  10.1021/tx000104n
• 作为产物：
  描述：

  1,2,3,4-四氢屈-1-酮 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 碘 、 sodium methylate 、 dinitrogen tetraoxide 、 碳酸氢钠 、 对甲苯磺酸 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 xylene 、 苯 为溶剂， 反应 22.42h， 生成 1,2-二氢-1,2-二羟基-6-硝基屈
  参考文献：
  名称：

  Synthesis of anti-1,2-Dihydroxy-3,4-epoxy-1,2,3,4-tetrahydro-6-nitrochrysene and Its Reaction with 2‘-Deoxyguanosine- 5‘-Monophosphate, 2‘-Deoxyadenosine-5‘-Monophosphate, and Calf Thymus DNA in Vitro

  摘要：

  The remarkable carcinogenic activity of 6-nitrochrysene (6-NC) in several animal models, and its environmental presence, suggest its potential importance with regard to human cancer development. Depending on the bioassay model, 6-NC can be activated by simple nitro reduction, ring oxidation, or by a combination of ring oxidation and nitro reduction. Only the first pathway has been clearly established. Thus, this study purports to unequivocally define the other pathways. Toward this end, we report for the first time the synthesis of anti-1,2-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydro-6-nitrochrysene (6-NCDE), a likely ultimate carcinogenic metabolite of 6-NC. Also, we describe our initial investigation of its binding with calf thymus DNA, 2'-deoxyguanosine-5'-monophosphate (2'-dGuo), and 2'-deoxyadenosine-5'-monophosphate (2'-dAdo) in vitro. These adduct markers were then employed for comparison with those obtained in the rat after in vivo treatment with 6-NC. On the basis of the results, it appears that the major adduct formed in the liver of rats treated with 6-NC is not derived from 6-NCDE.

  DOI：

  10.1021/tx000104n

文献信息

• Synthesis of <i>anti</i>-1,2-Dihydroxy-3,4-epoxy-1,2,3,4-tetrahydro-6-nitrochrysene and Its Reaction with 2‘-Deoxyguanosine- 5‘-Monophosphate, 2‘-Deoxyadenosine-5‘-Monophosphate, and Calf Thymus DNA in Vitro
  作者：Jacek Krzeminski、Dhimant Desai、Jyh-Ming Lin、Vladimir Serebryany、Karam El-Bayoumy、Shantu Amin

  DOI：10.1021/tx000104n

  日期：2000.11.1

  The remarkable carcinogenic activity of 6-nitrochrysene (6-NC) in several animal models, and its environmental presence, suggest its potential importance with regard to human cancer development. Depending on the bioassay model, 6-NC can be activated by simple nitro reduction, ring oxidation, or by a combination of ring oxidation and nitro reduction. Only the first pathway has been clearly established. Thus, this study purports to unequivocally define the other pathways. Toward this end, we report for the first time the synthesis of anti-1,2-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydro-6-nitrochrysene (6-NCDE), a likely ultimate carcinogenic metabolite of 6-NC. Also, we describe our initial investigation of its binding with calf thymus DNA, 2'-deoxyguanosine-5'-monophosphate (2'-dGuo), and 2'-deoxyadenosine-5'-monophosphate (2'-dAdo) in vitro. These adduct markers were then employed for comparison with those obtained in the rat after in vivo treatment with 6-NC. On the basis of the results, it appears that the major adduct formed in the liver of rats treated with 6-NC is not derived from 6-NCDE.