9-oxo-2-acetylamino-7-nitrofluorene | 7151-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-oxo-2-acetylamino-7-nitrofluorene
• 英文别名: N-(7-nitro-9-oxo-fluoren-2-yl)-acetamide；N-(7-Nitro-9-oxo-fluoren-2-yl)-acetamid；2-Acetylamino-7-nitro-fluoren-9-on；7-Nitro-2-acetamino-fluorenon；N-2-(7-Nitro-9-oxo-fluorenyl)-acetamid；N-(7-nitro-9-oxofluoren-2-yl)acetamide
• CAS: 7151-59-9
• 化学式: C₁₅H₁₀N₂O₄
• 分子量: 282.255
• InChiKey: AOWCVSUBBKOOGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-oxo-2-acetylamino-7-nitrofluorene 在 氯 、 三氯化铁 作用下， 生成 N-2-(3-Chlor-7-nitro-9-oxo-fluorenyl)-acetamid
  参考文献：
  名称：

  氟衍生物。18.新的卤素荧光素。I.潜在的抗肿瘤药物。

  摘要：

  DOI：

  10.1021/jm00331a008
• 作为产物：
  描述：

  N-(9-氧代芴-2-基)乙酰胺 在 硝酸 作用下， 生成 9-oxo-2-acetylamino-7-nitrofluorene
  参考文献：
  名称：

  Eckert; Langecker, Journal fur praktische Chemie (Leipzig 1954), 1928, vol. <2> 118, p. 269

  摘要：

  DOI：

文献信息

• DNA Adducts from Nitroreduction of 2,7-Dinitrofluorene, a Mammary Gland Carcinogen, Catalyzed by Rat Liver or Mammary Gland Cytosol
  作者：Clare L. Ritter、Sandra J. Culp、James P. Freeman、M. Matilde Marques、Frederick A. Beland、Danuta Malejka-Giganti

  DOI：10.1021/tx010172p

  日期：2002.4.1

  Nitrofluorenes are mutagenic and carcinogenic environmental pollutants arising chiefly from combustion of fossil fuels. Nitro aromatic compounds undergo nitroreduction to N-hydroxy arylamines that bind to DNA directly or after O-esterification. This study analyzes the DNA binding and adducts from the in vitro nitroreduction of 2,7-dinitrofluorene (2,7-diNF), a potent mammary carcinogen in the rat. Potential adduct(s) of 2,7-diNF was (were) generated by reduction of 2-nitroso-7-NF with ascorbate/H+ in the presence of calf thymus DNA. The major adduct was characterized by HPLC/ESI/MS and H-1 NMR spectrometry as N-(deoxyguanosin-8-yl)-2-amino-7-NF, and a minor one was determined by HPLC/ESI/MS to be a deoxyadenosine adduct of 2-amino-7-NF. Products from enzymatic nitroreduction were monitored by HPLC and DNA adduct formation by P-32-postlabeling. Xanthine oxidase/hypoxanthine-catalyzed nitroreduction of 2.7-diNF, 2-nitrofluorene (2-NF), and 1-nitropyrene (1-NP) yielded the respective amines to similar extents (30-50%). However, the level of the major adducts (similar to0.15/10(6) nucleotides) from 2-NF [N-(deoxyguanosin-8-yl)-2-aminofluorene] and 2,7-diNF [N-(deoxyguanosin-8-yl)-2-amino-7-NF] was less than or equal to2% that from 1-NP. In the presence of acetyl CoA, nitroreduction of 2-NF catalyzed by rat liver cytosol/NADH yielded the same adduct at a level of 2.2/10(6) nucleotides. Liver or mammary gland cytosol with acetyl CoA yielded mainly N-(deoxyguanosin-8-yl)-2-amino-7-NF from 2,7-diNF at >30 adducts/10(6) nucleotides, levels comparable to those from 1,6-dinitropyrene and 4- or 49-fold greater than the respective levels without acetyl CoA. Recovery of 2-nitroso-7-NF and 2-amino-7-NF from cytosol-catalyzed reduction of 2,7-diNF indicated nitroreduction and an N-hydroxy arylamine intermediate. Likewise, the presence of 2-acetylamino-7-NF indicated that reactivity with acyltransferase(s) was not prevented by the nitro group at C7. These data are consistent with activation of 2,7-diNF via nitroreduction to the N-hydroxy arylamine and acetyl CoA-dependent O-acetylation of the latter to bind to DNA. Enzymatic nitroreduction of 2,7-diNF was greatly enhanced by 9-oxidation. The nitroreduction of either 9-oxo-2,7-diNF or 9-hydroxy-2,7-diNF catalyzed by liver cytosol with acetyl CoA yielded two adducts (>2/10(6) nucleotides). Differences in the TLC migration of these adducts, compared to those from 2,7-diNF, and the lack of 2,7-diNF formation in the incubations suggested retention of the C9-oxidized groups. The relative ratios of the amine to amide from nitroreductions of 9-oxo-2,7-diNF and 2,7-diNF catalyzed by liver cytosol suggested that the 9-oxo group decreased reactivity with acyltransferase and, thus, the amount of N-acetoxy arylamine that binds to DNA. The mammary gland tumorigenicity of 2,7-diNF and the extent of its activation by the tumor target tissue shown herein suggest relevance of this environmental pollutant for breast cancer.
• Ishikawa; Hayashi, Yuki Gosei Kagaku Kyokaishi, 1957, vol. 15, p. 405,406
  作者：Ishikawa、Hayashi

  DOI：——

  日期：——
• Eckert; Langecker, Journal fur praktische Chemie (Leipzig 1954), 1928, vol. <2> 118, p. 269
  作者：Eckert、Langecker

  DOI：——

  日期：——
• Derivatives of Fluorene. XVIII. New Halogenofluorenes. I. Potential Antitumor Agents^1,2
  作者：Hsi-lung Pan、T. Lloyd Fletcher

  DOI：10.1021/jm00331a008

  日期：1964.1