(+/-)-10β-Azido-7β,8α,9α-trihydroxy-7,8,9,10-tetrahydrobenzopyrene

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: (+/-)-10β-Azido-7β,8α,9α-trihydroxy-7,8,9,10-tetrahydrobenzopyrene
• 英文别名: (+/-)-7β,8α,9α-trihydroxy-10β-azido-7,8,9,10-tetrahydrobenzopyrene；(7R,8S,9R,10S)-10-azido-7,8,9,10-tetrahydrobenzo[a]pyrene-7,8,9-triol
• 化学式: C₂₀H₁₅N₃O₃
• 分子量: 345.357
• InChiKey: ZBINGRRBSKACLB-NMLBUPMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75
• 氢给体数：
  3
• 氢受体数：
  5

上下游信息

反应信息

• 作为反应物：
  描述：

  (+/-)-10β-Azido-7β,8α,9α-trihydroxy-7,8,9,10-tetrahydrobenzopyrene 在 palladium on activated charcoal 吡啶 、 六甲基二硅氧烷 、 异丁酰胺 、 氨 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0~65.0 ℃ 、48.26 kPa 条件下， 反应 5.17h， 生成 (7R,8S,9R,10S)-N⁶-<10-(7,8,9-Triacetoxy-7,8,9,10-tetrahydrobenzopyrenyl)>-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis of Oligonucleotide Adducts of the Bay Region Diol Epoxide Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons

  摘要：

  An efficient method for the site-specific synthesis of adducts between the biologically active diol epoxide metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs) and oligonucleotides in which a PAH component of predetermined stereochemistry is linked covalently to the exocyclic amino groups of deoxyadenosine (dA) and deoxyguanosine (dG) is described. The synthetic strategy involves in the key step coupling a protected halopurine derivative with an amino derivative (or an aminotriol derivative) of the PAH. This method was initially employed to prepare the dA and dG adducts of the model PAH 1-methylpyrene. The appropriately protected dA adduct was then incorporated into the oligonucleotide sequence d(GCAGGTCA(*)AGAG) where A(*) represents N6-pyrenylmethyl-dA. This methodology was extended to the synthesis of trans adducts of anti-diol epoxide metabolites of benzo[a]pyrene and 5-methylchrysene linked to the 6-amino function of dA. The parent hydrocarbons are widespread environmental carcinogens. This synthetic approach, dubbed the total synthesis method, complements the direct synthesis method which involves the direct reaction of PAH diol epoxides with oligonucleotides. The total synthesis method is broader in scope than the latter, and it is readily adaptable to the large scale preparation of PAH-oligonucleotide adducts required for structure determination by high resolution NMR and X-ray crystallographic techniques.

  DOI：

  10.1021/jo00122a048
• 作为产物：
  描述：

  (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 在 sodium azide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 以61%的产率得到(+/-)-10β-Azido-7β,8α,9α-trihydroxy-7,8,9,10-tetrahydrobenzopyrene
  参考文献：
  名称：

  Synthesis of Oligonucleotide Adducts of the Bay Region Diol Epoxide Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons

  摘要：

  An efficient method for the site-specific synthesis of adducts between the biologically active diol epoxide metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs) and oligonucleotides in which a PAH component of predetermined stereochemistry is linked covalently to the exocyclic amino groups of deoxyadenosine (dA) and deoxyguanosine (dG) is described. The synthetic strategy involves in the key step coupling a protected halopurine derivative with an amino derivative (or an aminotriol derivative) of the PAH. This method was initially employed to prepare the dA and dG adducts of the model PAH 1-methylpyrene. The appropriately protected dA adduct was then incorporated into the oligonucleotide sequence d(GCAGGTCA(*)AGAG) where A(*) represents N6-pyrenylmethyl-dA. This methodology was extended to the synthesis of trans adducts of anti-diol epoxide metabolites of benzo[a]pyrene and 5-methylchrysene linked to the 6-amino function of dA. The parent hydrocarbons are widespread environmental carcinogens. This synthetic approach, dubbed the total synthesis method, complements the direct synthesis method which involves the direct reaction of PAH diol epoxides with oligonucleotides. The total synthesis method is broader in scope than the latter, and it is readily adaptable to the large scale preparation of PAH-oligonucleotide adducts required for structure determination by high resolution NMR and X-ray crystallographic techniques.

  DOI：

  10.1021/jo00122a048

文献信息

• Improved High-Yield Synthesis of Polycyclic Aromatic Hydrocarbon Amino Tribenzoates, Nucleophilic Components for Synthesis of Diol Epoxide-Nucleoside Adducts
  作者：Mahesh K. Lakshman、Surendrakumar Chaturvedi、Roland E. Lehr

  DOI：10.1080/00397919408010618

  日期：1994.11

  This report describes an improved high-yield synthesis of amino tribenzoates derived through a trans-ring opening of diol expoxides. A significant difference in the relative reactivities of benzo[a]pyrene series-1 and series-2 diol epoxide diastereomers with LiN3 has been noted. Facile triacylation of the azido triols derived through this ring-opening with benzoyl cyanide and reduction using PtO2 afforded the corresponding amines in high yields.
• Regioselective ring opening of polycyclic aromatic hydrocarbon epoxides by polymer-supported azide anion
  作者：Maheshkumar Lakshman、Durgesh V. Nadkarni、Roland E. Lehr

  DOI：10.1021/jo00303a025

  日期：1990.8
• Jhingan, Anil K.; Meehan, Thomas, Journal of Chemical Research, Miniprint, 1991, # 5, p. 1071 - 1083
  作者：Jhingan, Anil K.、Meehan, Thomas

  DOI：——

  日期：——
• Jhingan, Anil K.; Meehan, Thomas, Journal of Chemical Research, Miniprint, <hi>1991</hi>, # 5, p. 1071 - 1083
  作者：Jhingan, Anil K.、Meehan, Thomas

  DOI：——

  日期：——
• Synthesis of Oligonucleotide Adducts of the Bay Region Diol Epoxide Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons
  作者：Hongmee Lee、Ernestina Luna、Michael Hinz、John J. Stezowski、Alexander S. Kiselyo、Ronald G. Harvey

  DOI：10.1021/jo00122a048

  日期：1995.9

  An efficient method for the site-specific synthesis of adducts between the biologically active diol epoxide metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs) and oligonucleotides in which a PAH component of predetermined stereochemistry is linked covalently to the exocyclic amino groups of deoxyadenosine (dA) and deoxyguanosine (dG) is described. The synthetic strategy involves in the key step coupling a protected halopurine derivative with an amino derivative (or an aminotriol derivative) of the PAH. This method was initially employed to prepare the dA and dG adducts of the model PAH 1-methylpyrene. The appropriately protected dA adduct was then incorporated into the oligonucleotide sequence d(GCAGGTCA(*)AGAG) where A(*) represents N6-pyrenylmethyl-dA. This methodology was extended to the synthesis of trans adducts of anti-diol epoxide metabolites of benzo[a]pyrene and 5-methylchrysene linked to the 6-amino function of dA. The parent hydrocarbons are widespread environmental carcinogens. This synthetic approach, dubbed the total synthesis method, complements the direct synthesis method which involves the direct reaction of PAH diol epoxides with oligonucleotides. The total synthesis method is broader in scope than the latter, and it is readily adaptable to the large scale preparation of PAH-oligonucleotide adducts required for structure determination by high resolution NMR and X-ray crystallographic techniques.