trans-[PtCl₂{N(C(=O)(CH₂CO₂(methyl)))=CCH₂CH₂C(methyl)₂NH}₂]

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-[PtCl₂{N(C(=O)(CH₂CO₂(methyl)))=CCH₂CH₂C(methyl)₂NH}₂]
• 英文别名: dichloroplatinum;methyl 3-[(5,5-dimethyl-3,4-dihydropyrrol-2-yl)amino]-3-oxopropanoate
• 化学式: C₂₀H₃₂Cl₂N₄O₆Pt
• 分子量: 690.483
• InChiKey: MMUNJCUUXQEARQ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  trans-[PtCl₂{N=C(CH₂CO₂(methyl))ONC(H)CH₂CH₂C(methyl)₂}₂] 以 二氯甲烷 为溶剂， 反应 72.0h， 以89%的产率得到trans-[PtCl₂{N(C(=O)(CH₂CO₂(methyl)))=CCH₂CH₂C(methyl)₂NH}₂]
  参考文献：
  名称：

  Synthesis of Air Stable Fused Bicyclic D4-1,2,4-oxadiazoline Platinum(II) Complexes via [2+3] Cycloadditions

  摘要：

  反式-[PtCl2(NCR)2] [R1 = CH2CO2Me (1a)，R2 = CH2Cl (1b)]与吡咯啉 N-氧化物 -O+N=CHCH2CH2CMe2 (2)通过[2+3]环加成反应生成、新的融合双环 D4-1,2,4-恶二唑啉铂(II)配合物 trans-[PtCl2{N=C(R)ONC(H)CH2CH2CMe2}2]（R1 = CH2CO2Me (3a)，R2 = CH2Cl (3b)）。化合物 3a 和 3b 在 CH2Cl2 中回流，分别得到酮亚胺铂(II)配合物 trans-[PtCl2{N(C(=O)(R))=CCH2CH2C(Me2)NH}2] (R1 = CH2CO2Me (4a)，R2 = CH2Cl (4b))，这是化合物 3 中噁二唑啉环的 N-O 键裂解的结果。所有铂络合物都通过红外光谱、1H 和 13C NMR 光谱、ESI+-MS 和元素分析进行了表征。

  DOI：

  10.14233/ajchem.2015.18683

文献信息

• Synthesis, molecular structure and stability of fused bicyclic Δ4-1,2,4-oxadiazoline Pt(II) complexes
  作者：Jamal Lasri、Saied M. Soliman、M. Adília Januário Charmier、Mar Ríos-Gutiérrez、Luis R. Domingo

  DOI：10.1016/j.poly.2015.05.039

  日期：2015.9

  R2 = CH2Cl (1b)) with pyrroline N-oxide −O+NCHCH2CH2CMe2 (4), at room temperature for 15 min, furnishes via [3+2] cycloaddition the fused bicyclic Δ4-1,2,4-oxadiazoline Pt(II) complexes trans-[PtCl2NC(R)ONC(H)CH2CH2CMe2}2] (R1 = CH2CO2Me (5a), R2 = CH2Cl (5b)). Compounds 5a and 5b were refluxed in CH2Cl2 for 1 week to afford the derived ketoimine Pt(II) complexes trans-[PtCl2N(C(O)(R))CCH2CH2C(Me2)NH}2]

  的反应的反式- [氯铂酸2（NCR）2 ]（R 1  = CH 2 CO 2我（1A）中，R 2  = CH 2 Cl（上图1b）），与吡咯啉ñ -氧化物- ö + NCHCH 2 CH 2 CME 2（4）中，在室温下搅拌15分钟，配料经由[3 + 2]环加成的稠合双环Δ 4 -1,2,4-恶二唑啉铂（II）配合物的反式[氯铂酸2 NC（R）ONC（H CH 2 CH2 CME 2 } 2 ]（R 1  = CH 2 CO 2 Me（5a），R 2  = CH 2 Cl（5b））。将化合物5a和5b在CH 2 Cl 2中回流1周，以得到衍生的酮亚胺Pt（II）配合物，其反- [PtCl 2 N（C（O）（R））CCH 2 CH 2 C（Me 2）NH } 2 ]（R 1  = CH 2 CO 2 Me（6a），R 2 = CH 2 Cl（6b）），分别是由于5中的恶二唑啉环的N–O键断裂所致。通过IR，1
• Januario Charmier, M. Adilia; Haukka, Matti; Pombeiro, Armando J. L., Dalton Transactions
  作者：Januario Charmier, M. Adilia、Haukka, Matti、Pombeiro, Armando J. L.

  DOI：——

  日期：——
• Characterization of the antiproliferative potential and biological targets of a trans ketoimine platinum complex
  作者：Joana Silva、António Sebastião Rodrigues、Paula A. Videira、Jamal Lasri、Adília Januário Charmier、Armando J.L. Pombeiro、Alexandra R. Fernandes

  DOI：10.1016/j.ica.2014.07.067

  日期：2014.11

  The characterization of the antiproliferative potential of the ketoimine platinum complex trans[PtCl2RC(=O)N=CN-(H)C(Me)(2)-CH2CH2}(2)] (R = CH2CO2Me) is reported. It showed a higher cytotoxicity against HCT116 and HepG2 cancer cells (IC50 values of 22.74 +/- 0.04 mu M and 22.08 +/- 0.08 mu M, respectively) compared to fibroblasts and a non-tumorigenic cell line. It was also observed a moderate ability of the complex to induce apoptosis in HCT116 cells, as observed by fluorescence microscopy and flow cytometry. The observed antiproliferative activities of the complex are mostly due to delay in the cell cycle progression. In vitro DNA interaction studies revealed a DNA affinity constant of 6.67 x 10(5) M-1, suggesting a high affinity to DNA, by comparison to the value obtained for doxorubicin. A decrease in the electrophoretic mobility of the supercoiled plasmid DNA (pDNA) suggested the formation of complex-DNA adducts. However, the complex did not exhibit relevant genotoxicity in V79 cells. Proteomic assays demonstrated that the ketoimine Pt(II) complex promotes an overexpression of two negative cell cycle regulators, PA2G4 and 14-3-3 sigma, and PHB, and a decrease in expression of VDAC1 and HSP90B, probably associated with the antiproliferative potential. The ketoimine Pt(II) complex is able to trigger an overexpression of cytoskeleton-associated proteins in agreement with its ability to maintain cell structure, and an overexpression of oxidative stress enzymes, coping with the induction of ROS formation, observed by in vitro EMSA assays. In conclusion, the ketoimine Pt(II) complex is an antiproliferative agent with potential to be used against cancer cells. (C) 2014 Elsevier B.V. All rights reserved.