Cl2Pt(9-methyladenine-N7)(NH3) | 144673-45-0

• 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: Cl2Pt(9-methyladenine-N7)(NH3)
• CAS: 144673-45-0
• 化学式: C₆H₁₀Cl₂N₆Pt
• 分子量: 432.172
• InChiKey: YDAUSTSGMSTKLM-UHFFFAOYSA-L

反应信息

• 作为产物：
  描述：

  在 NH₃ 作用下， 以 水 为溶剂， 以90-95的产率得到Cl2Pt(9-methyladenine-N7)(NH3)
  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