1,9-二甲基嘌呤-6-亚胺,高氯酸 | 35234-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 1,9-二甲基嘌呤-6-亚胺,高氯酸
• 英文名称: 1,9-Dimethyladenin-Perchlorat
• 英文别名: 1,9-Dimethyladeninium perchlorate；1,9-dimethylpurin-1-ium-6-amine;perchlorate
• CAS: 35234-57-2
• 化学式: C₇H₁₀N₅*ClO₄
• 分子量: 263.64
• InChiKey: IGJKXWMCCBGXLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.34
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,9-二甲基嘌呤-6-亚胺,高氯酸 在 NH₃ 、 HCl 作用下， 以 盐酸 、 水 为溶剂， 生成 cis-{Cl2Pt(C5H3N4(NH)-1,9-(CH3)2-N7)(NH3)}Cl
  参考文献：
  名称：

  Metal-stabilized rare tautomers of nucleobases. 4. On the question of adenine tautomerization by a coordinated platinum(II)

  摘要：

  An attempt is described and critically asssessed to use the 'method of basicity measurements' for estimating the effect of Pt(II) electrophiles bound to the N7 position of the model nucleobase 9-methyladenine to shift the tautomer equilibrium from the preferred 6-amino to the rare 6-imino form. The question of tautomerization of an adenine nucleobase is of biological interest with regard to the now established preference for A --> T transversions as a consequence of 5' (ApG) adduct formation of the antitumor agent Cisplatin. For this purpose, a series of model nucleobase complexes of Pt(II) with 9-methyladenine (9-MeA), 1,9-dimethyladenine (1,9-DimeA) and 6,9-dimethyladenine ( 6,9-DimeA), and their protonated forms have been prepared and their UV spectra at various pH values recorded. In two cases, the compounds were characterized also by X-ray analysis, cis-[Cl2Pt(1,9-DimeAH)(NH3)]Cl (2c) and Cl3Pt(6,9-DimeAH) . H2O (3a). Based on the experimentally determined pK(a) values of the platinated adeninium ligands, tautomer equilibrium constants K(T) were calculated and found to be 10(-4.5) for [Cl3Pt(9-MeA)]- and 10(-4.6) for cis-Cl2Pt(NH3)(9-MeA). These values compare with 10(-4.8) for 9-MeA. The observed shifts in favor of the rare imino tautomer on Pt binding to N7 are considered too small to unambiguously explain the observed preferential A --> T transversion on the basis of an initial mispair between a platinated adenine in its imino form and an adenine in its normal amino tautomer.

  DOI：

  10.1016/s0020-1693(00)92417-4

文献信息

• Metal Coordination and Imine−Amine Hydrogen Bonding as the Source of Strongly Shifted Adenine p<i>K</i>_a Values
  作者：Michael Roitzsch、Bernhard Lippert

  DOI：10.1021/ja038834f

  日期：2004.3.3

  crystal structure of a Pt(II) complex of composition trans-[(NH(3))(2)Pt(1,9-DimeA) (1,9-DimeAH)](ClO(4))(3) (2) with 1,9-DimeA = 1,9-dimethyladenine and 1,9-DimeAH(+) = 1,9-dimethyladeninium) is presented. Complex 2 forms upon deprotonation of one of the exocyclic amino groups of the adeninium ligands in trans-[(NH(3))(2)Pt(1,9-DimeAH)(2)](ClO(4))(4) (1), where the two nucleobases are in a head-tail arrangement

  组成反式-[(NH(3))(2)Pt(1,9-DimeA) (1,9-DimeAH)](ClO(4))( 3) (2) 1,9-DimeA = 1,9-二甲基腺嘌呤和 1,9-DimeAH(+) = 1,9-二甲基腺嘌呤)。复合物 2 在反式-[(NH(3))(2)Pt(1,9-DimeAH)(2)](ClO(4))(4) 中腺嘌呤配体的环外氨基之一脱质子化后形成(1)，其中两个核碱基处于头尾排列。1 (4.1 +/- 0.2) 的低 pK(a1) 是金属配位对嘌呤碱 N7 的影响和去质子化物种的有效稳定相结合的结果。这一特征得到了 2 结构测定结果的支持，该结果显示了两个碱基的头-头取向以及 1,9-DimeA 的亚胺基团和 1,9-DimeAH 的氨基基团之间的分子内氢键. 在完全去质子化的物种 trans-[(NH(3))(2)Pt(1,9-DimeA)(2)](ClO(4))(2)
• Metal-stabilized rare tautomers of nucleobases. 4. On the question of adenine tautomerization by a coordinated platinum(II)
  作者：Bernhard Lippert、Helmut Schöllhorn、Ulf Thewalt

  DOI：10.1016/s0020-1693(00)92417-4

  日期：1992.8

  An attempt is described and critically asssessed to use the 'method of basicity measurements' for estimating the effect of Pt(II) electrophiles bound to the N7 position of the model nucleobase 9-methyladenine to shift the tautomer equilibrium from the preferred 6-amino to the rare 6-imino form. The question of tautomerization of an adenine nucleobase is of biological interest with regard to the now established preference for A --> T transversions as a consequence of 5' (ApG) adduct formation of the antitumor agent Cisplatin. For this purpose, a series of model nucleobase complexes of Pt(II) with 9-methyladenine (9-MeA), 1,9-dimethyladenine (1,9-DimeA) and 6,9-dimethyladenine ( 6,9-DimeA), and their protonated forms have been prepared and their UV spectra at various pH values recorded. In two cases, the compounds were characterized also by X-ray analysis, cis-[Cl2Pt(1,9-DimeAH)(NH3)]Cl (2c) and Cl3Pt(6,9-DimeAH) . H2O (3a). Based on the experimentally determined pK(a) values of the platinated adeninium ligands, tautomer equilibrium constants K(T) were calculated and found to be 10(-4.5) for [Cl3Pt(9-MeA)]- and 10(-4.6) for cis-Cl2Pt(NH3)(9-MeA). These values compare with 10(-4.8) for 9-MeA. The observed shifts in favor of the rare imino tautomer on Pt binding to N7 are considered too small to unambiguously explain the observed preferential A --> T transversion on the basis of an initial mispair between a platinated adenine in its imino form and an adenine in its normal amino tautomer.