cis-[Pt(pyrazine)2Cl2] | 81339-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: cis-[Pt(pyrazine)2Cl2]
• 英文别名: cis-[(pyrazine)2PtCl2]；cis-[PtCl2(pyrazine)2]；cis-[PtCl2(pz)2]；Dichloroplatinum;pyrazine；dichloroplatinum;pyrazine
• CAS: 81339-40-4
• 化学式: C₈H₈Cl₂N₄Pt
• 分子量: 426.164
• InChiKey: YDRDMHWRAOPFFM-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (imidazolium)[trans-RuCl4(DMSO)2] 、 cis-[Pt(pyrazine)2Cl2] 以 丙酮 为溶剂， 生成 [imidazolium]2(trans,cis,trans-[RuCl4(DMSO-S)(μ-pyrazine)]2PtCl2)
  参考文献：
  名称：

  Synthesis, Characterization, and in Vitro Evaluation of a Potentially Selective Anticancer, Mixed-Metal [Ruthenium(III)−Platinum(II)] Trinuclear Complex

  摘要：

  A new type of mixed-metal trinuclear complex containing platinum(II) and ruthenium(III) fragments that resemble both cisplatin and NAMI-A has been synthesized and characterized by IR, H-1 NMR, elemental analysis, and X-ray crystallography. The water-soluble compound Na-2{trans,cis,trans-[(RuCl4)-Cl-III(DMSO-S)(mu-pyz)](2)(PtCl2)-Cl-II} (AH-197, pyz = pyrazine) was assessed for its effects on DNA mobility and toxicity against human cancer cell lines. When compared to cisplatin and KP-1019 (which structurally resembles NAMI-A), IC50 results showed that AH-197 had an intermediate toxicity. When this data was coupled with a subsequent COMPARE evaluation (standard COMPARE queries resulted in insignificant correlation coefficients (<0.70) while very low COMPARE correlation coefficients were found in the matrix queries as well), AH-197 yielded a correlation coefficient of 0.19 when compared to cisplatin and 0.25 when compared to KP1019 indicating that AH-197 has a unique behavior.

  DOI：

  10.1021/ic062419h
• 作为产物：
  描述：

  吡嗪 、 trans-PtCl2(ethylene)(pyrazine) 生成 cis-[Pt(pyrazine)2Cl2]
  参考文献：
  名称：

  Siedle; Mann; Bohling, Inorganic Chemistry, 1985, vol. 24, # 14, p. 2216 - 2223

  摘要：

  DOI：

文献信息

• Synthesis and NMR characterization of the cis and trans isomers of [Ptii(N9-adeH)2(pz)2] and X-ray crystallography of the trans isomer
  作者：Karel D. Klika、Henri Kivelä、Vladimir V. Ovcharenko、Ville Nieminen、Reijo Sillanpää、Jorma Arpalahti

  DOI：10.1039/b709697f

  日期：——

  The reaction of tetrapyrazine Pt(II) with adenine under basic conditions yielded two products both disubstituted by adenine and bound in all cases to the N-9 nitrogen of adenine. Crystals amenable to X-crystallographic analysis were obtained for one product which was consequently identified as trans-[PtII(N9-adeH)2(pz)2](NO3)4·H2O. The other product, though, was identified as the cis isomer based on extensive and comparative NMR structural studies whereby the two compounds were examined as both neutral and tetraprotonated species in solution. The major product of the reaction was unexpectedly the cis isomer, thus obtained in contrast to the trans effect, and the reason for this result is speculated on. Computational calculations using DFT at the B3LYP/TZVP-MARI-J level of theory provided the head-to-tail conformer as the overwhelmingly more stable species over the head-to-head conformer for both compounds whilst the trans product was found to be more stable than the cis. Thus the reaction does not follow a thermodynamic course and rather is kinetically controlled in concert with the speculated mode of reaction.

  四吡嗪铂(II)与腺嘌呤在碱性条件下反应产生了两种产物，均由腺嘌呤二取代，并在所有情况下与腺嘌呤的 N-9 氮结合。其中一种产物可进行 X 射线晶体学分析，因此被确定为反式-[PtII(N9-adeH)2(pz)2](NO3)4-H2O。而另一种产物则被确定为顺式异构体，这是基于广泛的核磁共振结构比较研究，其中对两种化合物在溶液中的中性和四质子化状态进行了检验。反应的主要产物竟然是顺式异构体，这与反式效应形成了鲜明对比。利用 DFT 在 B3LYP/TZVP-MARI-J 理论水平上进行的计算表明，对于这两种化合物来说，头对尾构象比头对头构象更为稳定，而反式产物则比顺式更为稳定。因此，该反应并不遵循热力学过程，而是根据推测的反应模式进行动力学控制。
• The infrared spectra of the complexes cis- and trans-[Pt(pyrazine)2X2](X = Cl, Br, I, NO2)
  作者：Gary A. Foulds、David A. Thornton

  DOI：10.1016/0584-8539(81)80014-1

  日期：1981.1