(SP-4-3)-dichlorido(N,N-dimethylethane-1,2-diamine)platinum(II) | 41575-66-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (SP-4-3)-dichlorido(N,N-dimethylethane-1,2-diamine)platinum(II)
• 英文别名: N',N'-dimethylethane-1,2-diamine;platinum(2+);dichloride
• CAS: 41575-66-0
• 化学式: C₄H₁₂Cl₂N₂Pt
• 分子量: 354.139
• InChiKey: ZKNXUGMERRLUKL-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -6.49
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (SP-4-3)-dichlorido(N,N-dimethylethane-1,2-diamine)platinum(II) 在 盐酸 、 双氧水 作用下， 以 水 为溶剂， 生成 platinum(IV)Cl4(a-dmen)
  参考文献：
  名称：

  甲基的空间位阻对铂（IV）的N-甲基取代的乙二胺络合物的还原速率的作用

  摘要：

  FeCp 2 I -，[Pt（NH 2 Et）4 ] 2+或[Pt（en）（NH 2 Et）2 ] 2+对[PtCl 4（NN）]型铂（IV）配合物的还原在甲醇中存在氯离子的情况下，已经进行了研究（NN = en，meen，s- dmen，a- dmen，trimen，tmen）。该反应服从二阶或三阶速率定律：速率= ķ FeCp 2 [氯铂酸4（NN）] [FeCp 2，ķ我- [氯铂酸4（NN）] [I - ]或ķ的Pt II [氯铂酸4（NN）] [专利文献2 + 4 ] [氯- ]。速率常数增加通过在NN配体，的胺端基增加空间位阻，即使在测量值是定量地依赖于还原剂我- > FeCp 2 > [PT（NH 2的Et）4 ] 2+ ≈[ Pt（en）（NH 2 Et）2 ] 2+。末端胺基的空间位阻表现为加性参数，并且发现与反应性相关的线性关系（log k还原剂）铂（IV）配合物与NN

  DOI：

  10.1016/s0277-5387(00)83695-5
• 作为产物：
  描述：

  diiodo(N,N-dimethylethane-1,2-diamine)platinum(II) 、 sodium chloride 在 AgNO₃ 作用下， 以 水 为溶剂， 以69%的产率得到(SP-4-3)-dichlorido(N,N-dimethylethane-1,2-diamine)platinum(II)
  参考文献：
  名称：

  Synthesis and reactions of platinum(IV) complexes with sodium ascorbate

  摘要：

  The platinum(IV) complexes [PtCl2(OH)(2)((NN)-N-boolean AND)] ((NN)-N-boolean AND=en, N,N-dmen, N,N'-dmen) were prepared by oxidation of [PtCl2((NN)-N-boolean AND)] with hydrogen peroxide. The complexes were characterized by multinuclear NMR and infrared spectroscopy, as well as microanalysis. The reactions of these compounds with sodium ascorbate were monitored spectroscopically. Reduction of the platinum(IV) complexes by sodium ascorbate occurred only slowly. An oxalatoplatinum(IV) complex [Pt(C2O4)Cl(OH)(N(boolean AND)Ndmen)]. H2O was isolated from the reaction of [PtCl2(OH)(2)(N,N-dmen)] and sodium ascorbate and characterized by an X-ray diffraction study. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(02)01058-7

文献信息

• Trend in cytotoxic activity of a series of cis-[APtCl2] (A=ethylenediamine methylated at different positions) complexes
  作者：Marco Milanesio、Elena Monti、Marzia Bruna Gariboldi、Elisabetta Gabano、Mauro Ravera、Domenico Osella

  DOI：10.1016/j.ica.2008.02.004

  日期：2008.6

  is stronger for the non-methylated derivative with respect to the fully methylated congener. In addition, MM calculations were used to investigate the interactions between DNA and cis -[(P-L-A)PtCl 2 ] complexes [A = en group linked to an antiestrogen-like pharmacophore, P, via a –(CH 2 ) n – spacer ( n = 2, 4, 6, 8 and 10), L].

  摘要进行了一系列顺式[[APtCl 2]配合物（A =乙二胺，en，在不同位置甲基化）的研究，以评估不同甲基取代对所得衍生物的细胞毒性的影响。如预期的那样，发现差异甲基化复合物对人培养的卵巢癌细胞（A2780）的细胞毒性作用差异很大。已经进行了分子力学（MM）计算，以评估差异二胺甲基化与相应复合物与DNA相互作用时的排斥能之间的关系。由于其他甲基的空间位阻，与顺铂相比，以高能量成本结合DNA的化合物显示出较高的IC 50值（浓度抑制肿瘤细胞生长50％）。用DNA电化学生物传感器进行的半定量分析证实，相对于完全甲基化的同类物，顺式-[APtCl 2]配合物与沉积在电极上的ds-DNA之间的相互作用更强。此外，采用MM计算方法研究了DNA与顺式[[（PLA）PtCl 2]配合物[A =通过-（CH 2）n-间隔基连接到抗雌激素样药效团P的基团（ n = 2、4、6、8和10），L]。
• Unsymmetric Mono- and Dinuclear Platinum(IV) Complexes Featuring an Ethylene Glycol Moiety: Synthesis, Characterization, and Biological Activity
  作者：Verena Pichler、Petra Heffeter、Seied M. Valiahdi、Christian R. Kowol、Alexander Egger、Walter Berger、Michael A. Jakupec、Mathea Sophia Galanski、Bernhard K. Keppler

  DOI：10.1021/jm301645g

  日期：2012.12.27

  SW1573, 2R120, and 2R160) with regard to their resistance patterns, offering a distinctly different scheme compared to cisplatin. To gain further insights into the mode of action, drug uptake, DNA synthesis inhibition, cell cycle effects, and induction of apoptosis were determined for two characteristic substances.

  合成了八种新型单核和两种双核铂 (IV) 配合物，并通过元素分析、一维和二维 NMR 光谱、质谱和反相 HPLC (log  k w ) 以及在一种情况下通过 X 射线衍射对其进行了表征. 通过 MTT 测定法在三种人类癌细胞系（CH1、SW480 和 A549）中研究了化合物的细胞毒性，IC 50值到低微摩尔范围。此外，在其他癌细胞系（P31 和 P31/顺式、A2780 和 A2780/顺式、SW1573、2R120 和 2R160）中研究了一组选定的化合物的抗性模式，提供了与顺铂截然不同的方案。为了进一步了解作用方式，确定了两种特征物质的药物摄取、DNA 合成抑制、细胞周期效应和细胞凋亡诱导。
• Mono-carboxylated diaminedichloridoplatinum(<scp>iv</scp>) complexes – selective synthesis, characterization, and cytotoxicity
  作者：Verena Pichler、Seied M. Valiahdi、Michael A. Jakupec、Vladimir B. Arion、Mathea S. Galanski、Bernhard K. Keppler

  DOI：10.1039/c1dt10301f

  日期：——

  Selective mono-carboxylation of (OC-6-43)-dichlorido(N,N-dimethyl-ethane-1,2-diamine)dihydroxido platinum(iv) with succinic anhydride and subsequent esterification afforded novel cytotoxic platinum complexes with IC₅₀ values down to the low nanomolar range.

  通过琥珀酸酐对（OC-6-43）-二氯（N，N-二甲基乙二胺）二羟基铂（IV）进行选择性单羧化，然后进行酯化反应，得到了新的细胞毒性铂配合物，其IC50值降至低纳摩尔范围。
• Reaction of chlorine with platinum(IV) triamine containing N,N-dimethylethylenediamine. The crystal structure of [Pt{(CH3)2N(CH2)2NH2}PyCl3]Cl·H2O[Pt{(CH3)2N(CH2)2NCl}PyCl3], and [Pt{(CH3)2N(CH2)2NH2}PyCl4]
  作者：T. N. Fedotova、G. G. Aleksandrov、G. N. Kuznetsova

  DOI：10.1134/s0036023608120061

  日期：2008.12

  Platinum(II) diamine with N,N-dimethylethylenediamine (N,N-dimeEn) [Pt(CH(3))(2)N(CH(2))(2)NH(2)}Cl(2)] (I) was synthesized. The reaction of the diamine with pyridine gave Pt(II) tetramine [Pt(CH(3))(2)N(CH(2))(2)NH(2)}Py(2)]Cl(2) (II), which was oxidized with chlorine to give Pt(IV) triamine Pt[(CH(3))(2)N(CH(2))(2)}PyCl(3)]Cl center dot H(2)O (III). The reaction of III with chlorine (chloroamidation) yielded chloroimide [Pt(CH(3))(2)N(CH(2))(2)NCl}PyCl(3)] (IV). The IR spectra of complexes I-IV and UV/Vis spectra of III and IV were studied. X-Ray diffraction analysis was performed for III (monoclinic crystals, space group P2(1)/c, a = 7.7437(6), b = 8.1100(7), c = 28.52992(2) angstrom, beta = 93.7280(10)degrees, Z = 4, R(hkl) = 0.0420) and IV (orthorhombic crystals, space group Pna2(1), a = 15.7825(12), b = 7.4447(6), c = 12.3099(6) angstrom, Z = 4, R(hkl) = 0.0539). During oxidation of Pt(II) tetramine with chlorine, the pyridine molecule is removed from the cis position relative to the (CH(3))(2)N group (trans position relative to the NH(2) group) of N,N-dimethylethylenediamine. The reaction of chloroimide complex IV with concentrated HCl (dechloroamidation) at 20 degrees C afforded the initial complex III; that at 100 degrees C, gave triamine III together with Pt(IV) diamine [Pt( N,N-dimeEn)Cl(4)] (V) (monoclinic crystals, space group P2(1)/n, a = 7.1278(5), b = 11.5384(8), c = 12.7501(9) angstrom, beta = 93.23(10)degrees, Z = 4, R(hkl) = 0.0239).
• Berners-Price, Susan J.; Frey, Urban; Ranford, John D., Journal of the American Chemical Society, 1993, vol. 115, # 19, p. 8649 - 8659
  作者：Berners-Price, Susan J.、Frey, Urban、Ranford, John D.、Sadler, Peter J.

  DOI：——

  日期：——