4-羟基雌酮1-N7-鸟嘌呤 | 178971-92-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 4-羟基雌酮1-N7-鸟嘌呤
• 英文名称: 7-[4-hydroxyestron-1(α,β)-yl]guanine
• 英文别名: N7-(4-hydroxyestron-1-yl)deoxyguanine；4-Hydroxy Estrone 1-N7-Guanine；2-amino-7-[(8R,9S,13S,14S)-3,4-dihydroxy-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-1-yl]-1H-purin-6-one
• CAS: 178971-92-1
• 化学式: C₂₃H₂₅N₅O₄
• 分子量: 435.483
• InChiKey: LBPGOOJJEWNDMR-MQGMTOSNSA-N

物化性质

• 熔点：
  >260°C (dec.)
• 溶解度：
  可溶于DMSO（轻微、超声处理）、乙醇（加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-羟基雌酮1-N7-鸟嘌呤 、 N,N'-bis-anthracen-9-ylmethyl-2,2-dibromomalonamide 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (5bS,7aS,10aS,10bR)-5-(2-Amino-6-oxo-1,6-dihydro-purin-7-yl)-7a-methyl-8-oxo-6,7,7a,8,9,10,10a,10b,11,12-decahydro-5bH-1,3-dioxa-dicyclopenta[a,i]phenathrene-2,2-dicarboxylic acid bis-[(anthracen-9-ylmethyl)-amide]
  参考文献：
  名称：

  Synthesis of a New Fluorescent Probe Specific for Catechols

  摘要：

  [GRAPHICS]The synthesis of a new fluorescent probe, specific for the catechol moiety, has been conducted by preparation of alpha,alpha-dibromomalonamides containing an appropriate fluorophore. N,N'-Bis-anthracen-9-ylmethyl-2,2-dibromomalonamide reacted with various catechols in the presence of cesium carbonate to generate highly fluorescent derivatives.

  DOI：

  10.1021/ol027000j
• 作为产物：
  描述：

  4-羟雌甾酮 在 manganese(IV) oxide 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 5.17h， 生成 4-羟基雌酮1-N7-鸟嘌呤
  参考文献：
  名称：

  Molecular Characteristics of Catechol Estrogen Quinones in Reactions with Deoxyribonucleosides

  摘要：

  Estrogens can have two roles in the induction of cancer: stimulating proliferation of cells by receptor-mediated processes, and generating electrophilic species that can covalently bind to DNA. The latter role is thought to proceed through catechol estrogen metabolites, which can be oxidized to o-quinones that bind to DNA. Four estrogen-deoxyribonucleoside adducts were synthesized by reaction of estrone 3,4-quinone (E(1)-3,4-Q), 17 beta-estradiol 3,4-quinone (E(2)-3,4-Q), or estrone 2,3-quinone (E(1)-2,3-Q) with deoxyguanosine (dG) or deoxyadenosine (dA) in CH3CO2H/H2O (1:1). Reaction of E(1)-3,4-Q or E(2)-3,4-Q with dG produced specifically 7-[4-hydroxyestradiol-1(alpha,beta)-yl]guanine (4-OHE(1)-1(alpha,beta)-N7Gua) or 7-[4-hydroxyestradiol-1(alpha,beta)-yl]-guanine (4-OHE(2)-1(alpha,beta)-N7Gua), respectively, in 40% yield, with loss of deoxyribose. These two quinones did not react with dA, deoxycytidine, or thymidine. When E(1)-2,3-Q was reacted with dG or dA, N-2-(2 -hydroxyestron-6-yl)deoxyguanosine (2-OHE(1)-6-N(2)dG, 10% yield) and N-6-(2-hydroxyestron-6-yl)deoxyadenosine (2-OHE(1)-6-N(6)dA, 80% yield), respectively, were formed. These adducts provide insight into the type of DNA damage that can be caused by o-quinones of the catechol estrogens. The estrogen 3,4-quinones are expected to produce depurinating guanine adducts that are lost from DNA, generating apurinic sites, whereas the 2,3-quinones would form stable adducts that remain in DNA, unless repaired. The adducts reported here will be used as references in studies to elucidate the structure of estrogen adducts in biological systems.

  DOI：

  10.1021/tx960002q

文献信息

• Estrogen−Nucleic Acid Adducts:  Dissection of the Reaction of 3,4-Estrone Quinone and Its Radical Anion and Radical Cation with Deoxynucleosides and DNA
  作者：Abraham Akanni、Yusuf J. Abul-Hajj

  DOI：10.1021/tx9900932

  日期：1999.12.1

  both deoxynucleosides and calf thymus DNA under different pH conditions. Both stable and unstable adducts with guanine and thymine were observed from reactions with DNA. Although adduct levels were somewhat different, the adduct profiles obtained from reactions of 3,4-EQ and its radical anion with both DNA and deoxynucleosides were quite similar and were found to be significantly different from product

  我们实验室的先前研究表明，3,4-雌酮醌（3,4-EQ）可以氧化还原循环，并能够诱导MCF-7乳腺癌细胞中的单链DNA断裂，并能与多种脱氧核苷反应得到几种雌激素-核酸加合物。3,4-EQ与所有脱氧核苷在酸性条件下的反应仅产生N7-Gua加合物，可通过迈克尔加成反应进行；而3,4-EQ在还原条件下的反应可产生数种加合物，包括N7-Gua， C8-Ade，C8-Gua，N3-Thy和N4-Cyt加合物，表明涉及3,4-EQ自由基物种。关于哪个反应物种是引起雌激素的基因毒性活性的反应物种是雌激素醌或雌激素半醌，已经成为一些实验室最近研究的主题。为了更详细地探讨这一点，我们在不同pH条件下对3,4-EQ，3,4-EQ自由基阴离子和3,4-EQ自由基阳离子与脱氧核苷和小牛胸腺DNA的反应性进行了研究。 。鸟嘌呤和胸腺嘧啶的稳定加合物和不稳定加合物都可以从与DNA的反应中观察到。尽管加合物的水平有些不同，但是从3
• Synthesis of a New Fluorescent Probe Specific for Catechols
  作者：Douglas E. Stack、Anastacia L. Hill、Clark B. Diffendaffer、Nicole M. Burns

  DOI：10.1021/ol027000j

  日期：2002.12.1

  [GRAPHICS]The synthesis of a new fluorescent probe, specific for the catechol moiety, has been conducted by preparation of alpha,alpha-dibromomalonamides containing an appropriate fluorophore. N,N'-Bis-anthracen-9-ylmethyl-2,2-dibromomalonamide reacted with various catechols in the presence of cesium carbonate to generate highly fluorescent derivatives.
• Molecular Characteristics of Catechol Estrogen Quinones in Reactions with Deoxyribonucleosides
  作者：Douglas E. Stack、Jaeman Byun、Michael L. Gross、Eleanor G. Rogan、Ercole L. Cavalieri

  DOI：10.1021/tx960002q

  日期：1996.1.1

  Estrogens can have two roles in the induction of cancer: stimulating proliferation of cells by receptor-mediated processes, and generating electrophilic species that can covalently bind to DNA. The latter role is thought to proceed through catechol estrogen metabolites, which can be oxidized to o-quinones that bind to DNA. Four estrogen-deoxyribonucleoside adducts were synthesized by reaction of estrone 3,4-quinone (E(1)-3,4-Q), 17 beta-estradiol 3,4-quinone (E(2)-3,4-Q), or estrone 2,3-quinone (E(1)-2,3-Q) with deoxyguanosine (dG) or deoxyadenosine (dA) in CH3CO2H/H2O (1:1). Reaction of E(1)-3,4-Q or E(2)-3,4-Q with dG produced specifically 7-[4-hydroxyestradiol-1(alpha,beta)-yl]guanine (4-OHE(1)-1(alpha,beta)-N7Gua) or 7-[4-hydroxyestradiol-1(alpha,beta)-yl]-guanine (4-OHE(2)-1(alpha,beta)-N7Gua), respectively, in 40% yield, with loss of deoxyribose. These two quinones did not react with dA, deoxycytidine, or thymidine. When E(1)-2,3-Q was reacted with dG or dA, N-2-(2 -hydroxyestron-6-yl)deoxyguanosine (2-OHE(1)-6-N(2)dG, 10% yield) and N-6-(2-hydroxyestron-6-yl)deoxyadenosine (2-OHE(1)-6-N(6)dA, 80% yield), respectively, were formed. These adducts provide insight into the type of DNA damage that can be caused by o-quinones of the catechol estrogens. The estrogen 3,4-quinones are expected to produce depurinating guanine adducts that are lost from DNA, generating apurinic sites, whereas the 2,3-quinones would form stable adducts that remain in DNA, unless repaired. The adducts reported here will be used as references in studies to elucidate the structure of estrogen adducts in biological systems.