7-(2-hydroxy-2-phenylethyl)guanine | 77816-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 7-(2-hydroxy-2-phenylethyl)guanine
• 英文别名: 2-amino-7-(2-hydroxy-2-phenylethyl)purin-6-one；2-Amino-7-(2-hydroxy-2-phenylethyl)-1H-purin-6(7H)-one；2-amino-7-(2-hydroxy-2-phenylethyl)-1H-purin-6-one
• CAS: 77816-18-3
• 化学式: C₁₃H₁₃N₅O₂
• 分子量: 271.279
• InChiKey: XYLRBCXLUCNYQO-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C(Solv: isopropanol (67-63-0); water (7732-18-5))
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-6-氯嘌呤 在 四(三苯基膦)钯 sodium hydroxide 、 potassium carbonate 、 zinc(II) chloride 、 poly(methylhydrosiloxane) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 7-(2-hydroxy-2-phenylethyl)guanine
  参考文献：
  名称：

  7-(2-羟基-1-苯乙基)-和7-(2-羟基-2-苯乙基)鸟嘌呤的合成，来源于苯乙烯7,8-氧化物的DNA加合物

  摘要：

  7-(2-羟基-1-苯乙基)-和7-(2-羟基-2-苯乙基)鸟嘌呤是重要的DNA加合物，可用作暴露于苯乙烯的标记。使用烯丙基保护的溴醇作为氧化苯乙烯的合成等效物来烷基化 2-amino-6-chloropurine 或 7-methyl-10-oxo-9,10-dihydropyrimido[1,2-a] 提出了导致这些化合物的两种合成路线嘌呤是鸟嘌呤的前体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200300811

文献信息

• Comparison of ethylene, propylene and styrene 7,8-oxide in vitro adduct formation on N-terminal valine in human haemoglobin and on N-7-guanine in human DNA
  作者：W Pauwels、H Veulemans

  DOI：10.1016/s1383-5718(98)00106-5

  日期：1998.9

  nucleophilic sites in macromolecules such as haemoglobin and DNA. To study the reaction rate constants of ethylene oxide (EO), propylene oxide (PO) and styrene 7,8-oxide (SO) towards two of these positions, i.e., the N-terminal valine in haemoglobin and N-7-guanine in DNA was the central aim of this investigation. These two reactive sites are the most studied haemoglobin and DNA adducts, respectively. Further

  环氧化合物在大分子的各种亲核位点（如血红蛋白和DNA）反应。为了研究环氧乙烷（EO），环氧丙烷（PO）和苯乙烯7,8-氧化物（SO）在其中两个位置上的反应速率常数，即血红蛋白中的N末端缬氨酸和N-7鸟嘌呤中的DNA是这项研究的主要目标。这两个反应性位点分别是研究最多的血红蛋白和DNA加合物。因此，还进一步关注了体外测定的反应常数在体内的适用性。Hb [分别为2.7 l（mol Hb h）-1和1.0 l（mol Hb h）-1]中EO和PO与N末端缬氨酸之间的二级速率常数的测定与文献值一致。与N-7-鸟嘌呤[16x10（-3）l（mol DNA核苷酸h）-1和7的反应常数。[分别为7x10（-3）l（mol DNA核苷酸h）-1]低于以前发表的值，可能是由于所使用的方法不同。使用体外获得的值对体内情况进行建模可得到EO和PO的一致图片。相反，对于SO，N末端缬氨酸[1.5 l（mol Hb
• Synthesis of 3-(2-hydroxy-1-phenylethyl)- and 3-(2-hydroxy-2-phenylethyl)adenine, DNA adducts derived from styrene
  作者：Jan Krouželka、Igor Linhart、Tomáš Tobrman

  DOI：10.1002/jhet.5570450325

  日期：2008.5

  3-(2-Hydroxy-2-phenylethyl)- and 3-(2-hydroxy-1-phenylethyl)adenine, DNA adducts derived from styrene, along with their 9-substituted analogues were prepared by alkylation of 8-bromoadenine with corresponding allyl-protected bromohydrins followed by a new deallylation procedure using tetrakis(triphenylphosphine)palladium catalyzed reductive cleavage by poly(methylhydrosiloxane) in the presence of p-toluenesulphonic

  3-（2-羟基-2-苯基乙基）-和3-（2-羟基-1-苯基乙基）腺嘌呤，苯乙烯衍生的DNA加合物及其9-取代的类似物是通过将8-溴腺嘌呤与相应的烯丙基烷基化而制备的-保护的溴代醇，然后采用新的脱羧方法，使用四（三苯基膦）钯在对甲苯磺酸的存在下，通过聚（甲基氢硅氧烷）催化还原裂解。事实证明，该新方法对于嘌呤衍生物是有用的，嘌呤衍生物对其他脱羧方法具有抗性。使用2D NMR实验HMBC和HMQC指定位置异构体的结构。
• Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles
  作者：Michael R. Paillasse、Nathalie Saffon、Heinz Gornitzka、Sandrine Silvente-Poirot、Marc Poirot、Philippe de Medina

  DOI：10.1194/jlr.m023689

  日期：2012.4

  We recently established that drugs used for the treatment and the prophylaxis of breast cancers, such as tamoxifen, were potent inhibitors of cholesterol-5,6-epoxide hydrolase (ChEH), which led to the accumulation of 5,6 alpha-epoxy-cholesterol (5,6 alpha-EC) and 5,6 beta-epoxy-cholesterol (5,6 beta-EC). This could be considered a paradox because epoxides are known as alkylating agents with putative carcinogenic properties. We report here that, as opposed to the carcinogen styrene-oxide, neither of the ECs reacted spontaneously with nucleophiles. Under catalytic conditions, 5,6 beta-EC remains unreactive whereas 5,6 alpha-EC gives cholestan-3 beta,5 alpha-diol-6 beta-substituted compounds. These data showed that 5,6-ECs are stable epoxides and unreactive toward nucleophiles in the absence of a catalyst, which contrasts with the well-known reactivity of aromatic and aliphatic epoxides.(jlr) These data rule out 5,6-EC acting as spontaneous alkylating agents. In addition, these data support the existence of a stereoselective metabolism of 5,6 alpha-EC.-Paillasse, M. R., N. Saffon, H. Gornitzka, S. Silvente-Poirot, M. Poirot, and P. de Medina. Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles. J. Lipid Res. 2012. 53: 718-725.
• Synthesis of 7-Hydroxy(phenyl)ethylguanines by Alkylation of 2-Amino-6-chloropurine with Allyl-Protected Bromohydrins
  作者：Jan Novák、Igor Linhart、Hana Dvořáková、Vladislav Kubelka

  DOI：10.1021/ol0272803

  日期：2003.3.1

  [GRAPHICS]Protecting the hydroxyl group in both 2-bromo-2-phenylethanol and 2-bromo-1-phenylethanol enhanced the alkylation of 2-amino-6-chloropurine to give corresponding 7- and 9-alkylated products. Subsequent hydrolysis and deprotection led to 7- and 9-hydroxy(phenyl)ethylguanines. 7-Hydroxy(phenyl)ethylguanines are major guanine adducts formed by interaction of styrene 7,8-oxide with DNA.
• Syntheses of 7-(2-Hydroxy-1-phenylethyl)- and 7-(2-Hydroxy-2-phenylethyl)guanine, DNA Adducts Derived from Styrene 7,8-Oxide
  作者：Jan Novák、Igor Linhart、Hana Dvorˇáková

  DOI：10.1002/ejoc.200300811

  日期：2004.6

  7-(2-Hydroxy-1-phenylethyl)- and 7-(2-hydroxy-2-phenylethyl)guanines are important DNA adducts which can be used as markers of exposure to styrene. Two synthetic routes leading to these compounds are presented using allyl-protected bromohydrins as synthetic equivalents of styrene oxide to alkylate 2-amino-6-chloropurine or 7-methyl-10-oxo-9,10-dihydropyrimido[1,2-a]purine as precursors to guanine. (© Wiley-VCH

  7-(2-羟基-1-苯乙基)-和7-(2-羟基-2-苯乙基)鸟嘌呤是重要的DNA加合物，可用作暴露于苯乙烯的标记。使用烯丙基保护的溴醇作为氧化苯乙烯的合成等效物来烷基化 2-amino-6-chloropurine 或 7-methyl-10-oxo-9,10-dihydropyrimido[1,2-a] 提出了导致这些化合物的两种合成路线嘌呤是鸟嘌呤的前体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)