(+/-)-7β,8α,9α-trihydroxy-10β-amino-7,8,9,10-tetrahydrobenzopyrene | 128084-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: (+/-)-7β,8α,9α-trihydroxy-10β-amino-7,8,9,10-tetrahydrobenzopyrene
• 英文别名: (7R,8S,9R,10S)-10-amino-7,8,9,10-tetrahydrobenzo[a]pyrene-7,8,9-triol
• CAS: 128084-01-5；134732-11-9；138664-24-1；144731-69-1
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: BSENDADLTGEXDE-NMLBUPMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

上下游信息

反应信息

• 作为反应物：
  描述：

  (+/-)-7β,8α,9α-trihydroxy-10β-amino-7,8,9,10-tetrahydrobenzopyrene 在 吡啶 、 六甲基二硅氧烷 、 异丁酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 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：

  (7S,8R,9S,10R)-10-azido-7,8,9,10-tetrahydrobenzo[a]pyrene-7,8,9-triol 以100%的产率得到
  参考文献：
  名称：

  JHINGAN, ANIL K.;MEEHAN, THOMAS, J. CHEM. RES. (S),(1991) N, C. 122-123

  摘要：

  DOI：

文献信息

• Enantioselective synthesis of the (+)-anti-7,8-dihydrodiol-9,10-epoxide of the potent carcinogen benzo[a]pyrene
  作者：Xiaoming Huang、Thomas M. Harris

  DOI：10.1039/c39950001699

  日期：——

  The title compound, the most important genotoxic metabolite of benzo[a]pyrene, has been prepared efficiently in a synthesis which capitalized on Jacobsen-type enantioselective epoxidation of 9,10-dihydrobenzo[a]pyrene, cleavage of the epoxide by KOH–Me2SO to give the tetrahydro-trans-7,8-diol, and formation of the dibenzoate from which the contaminating antipode was removed by crystallization.

  利用 9,10- 二氢苯并[a]芘的雅各布森型对映体选择性环氧化作用、环氧化物在 KOH-Me2SO 作用下裂解生成四氢-反式-7,8-二醇，并形成二苯甲酸酯，通过结晶去除其中的污染性反式，从而高效地制备出了苯并[a]芘最重要的基因毒性代谢物--标题化合物。
• Non-biomimetic route to deoxyadenosine adducts of carcinogenic polycyclic aromatic hydrocarbons
  作者：Seong Jin Kim、Constance M. Harris、Kee-Yong Jung、Masato Koreeda、Thomas M. Harris

  DOI：10.1016/0040-4039(91)80756-v

  日期：1991.10

  Aminotriols are prepared by direct aminolysis of the diol epoxides of polycyclic aromatic hydrocarbons, providing a substantial improvement over literature methods. The condensation of aminotriols with 6-halopurine deoxyribonucleosides provides a regio- and stereospecific synthesis of deoxyadenosine N6 adducts.

  氨基三醇是通过多环芳族烃的二醇环氧化物的直接氨解制备的，与文献方法相比有实质性的改进。氨基三醇与6-卤代嘌呤脱氧核糖核苷的缩合提供了脱氧腺苷N 6加合物的区域和立体特异性合成。
• Synthesis of Deoxyadenosine 3‘-Phosphates Bearing <i>Cis</i> and <i>Trans</i> Adducts of 7β,8α-Dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[<i>a</i>]pyrene:  Standards for ³²P-Postlabeling Assays
  作者：Shin Han、Constance M. Harris、Thomas M. Harris、Hye-Young Hong Kim、Seong J. Kim

  DOI：10.1021/jo9510898

  日期：1996.1.1

  Deoxyadenosine 3'-phosphates bearing cis and trans N-6 adducts of (7R) and (7S)-anti 7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9, 10-tetrahydrobenzo[alpha]pyrenes have been prepared in good yield by reaction of 6-fluoropurinyl 2'-deoxyriboside 3'-(bis(2-[4-nitrophenyl]ethyl)phosphate with the (+/-)(7 beta,8 alpha,9 alpha,10 beta)- and (+/-)-(7 beta,8 alpha,9 alpha,10 alpha)-10-amino-7,8,9,10-tetrahydrobenzo[alpha]pyrene-7,8,9-triols. The protected phosphates are easily prepared as diasteromeric mixtures, readily resolved by reversed phase HPLC, and efficiently deprotected with DBU to give the adducted S'-phosphates. These nucleotides are of value as standards for the P-32-postlabeling procedure of Randerath for determination of benzo[alpha]pyrene adducts in DNA (Reddy et al. Carcinogenesis 1984, 5, 231).
• 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：——