trans-[PtCl₂(NCCH₂CO₂(methyl))₂] | 777062-61-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-[PtCl₂(NCCH₂CO₂(methyl))₂]
• 英文别名: trans-[PtCl₂(NCCH₂CO₂Me)₂]；trans-[PtCl2(MeCO2CH2CN)2]；trans-[PtCl2(NCCH2CO2Me)2]；Dichloroplatinum;methyl 2-cyanoacetate
• CAS: 777062-61-0；953822-30-5
• 化学式: C₈H₁₀Cl₂N₂O₄Pt
• 分子量: 464.164
• InChiKey: NDSQIBZUJOMZTP-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trans-[PtCl₂(NCCH₂CO₂(methyl))₂] 、 丙酮肟 以 二氯甲烷 为溶剂， 以50%的产率得到trans-[PtCl2(NH=C(CH2CO2Me)ON=CMe2)2]
  参考文献：
  名称：

  酮肟与活化的有机腈配体的亚氨基酰化直接合成（亚胺）铂（II）配合物

  摘要：

  金属介导的亚氨基酰化 酮肟R 1 R 2 C NOH（1a R 1 = R 2 = Me; 1b R 1 = Me，R 2 = Et; 1c R 1 R 2 = C 4 H 8 ; 1d R 1 R 2 = C 5 H 10）铂（II）配合物反式-[PtCl 2（NCCH 2 CO 2 Me）2 ] 2a处理带有受体基团的有机腈在温和的条件下在干燥的CH 2 Cl 2中进行，以中等收率得到反式-[PtCl 2 {NH C（CH 2 CO 2 Me）ON CR 1 R 2 } 2 ] 3a-d异构体。那些人的反应酮肟在相同的实验条件下用反式-[PtCl 2（NCCH 2 Cl）2 ] 2b生成异构体反式/顺式-[PtCl 2 {NH C（CH 2 Cl）ONCR 1 R 2 } 2的1：1混合物] 3e–h和4e–h，产量中等至良好。微波辐射极大地促进了这些反应，从而以更高的收率（约75％）提供了相同的产物，其特征在于红外和1

  DOI：

  10.1039/b611341a
• 作为产物：
  描述：

  氰乙酸甲酯 、 trans-[PtCl₂(EtCN)2] 以 二氯甲烷 为溶剂， 以85%的产率得到trans-[PtCl₂(NCCH₂CO₂(methyl))₂]
  参考文献：
  名称：

  Januario Charmier, M. Adilia; Haukka, Matti; Pombeiro, Armando J. L., Dalton Transactions

  摘要：

  DOI：

文献信息

• Optically Active Mixed Unsymmetric Imine Platinum(II) Complexes – Utilization of the Liberated Imines for Further Syntheses of Mixed Imine‐Diazadiene Complexes and of ( <i>E</i> )‐Cyanoalkenes
  作者：Jamal Lasri、M. Fátima C. Guedes da Silva、M. Adília Januário Charmier、Armando J. L. Pombeiro

  DOI：10.1002/ejic.200800343

  日期：2008.8

  in better yields (71-50%), the same products. The new optically active diimine compounds NH=C(R)ON=C-(CgH 16 ) (8) are quantitatively liberated upon reaction of complexes 7 with a diphosphane. The chiral diimino ester 8a (R = CH 2 CO 2 Me) acts as a protic nucleophile and efficiently couples with the coordinated nitrile in 4 to give the new optically active, mixed, unsymmetric imine-1,3-diaza-1,3-diene

  用 (R*)-樟脑肟 (C 9 H 16 )C=NOH (R*) 处理反式-[PtC1 2 (NCR) 2 ] (1) R = CH 2 CO 2 Me (la), Ph (1b)} ( 2) 获得旋光混合亚胺-腈络合物反式-(R*)-[PtCl 2 NH=C(R)ON=C(C 9 H 16 )}(NCR)] (4)，其中，与酮肟反应 R 1 R 2 C=NOH (3) R 1 =R 2 = Me (3a), C 4 H 8 (3b)}，得到手性不对称双（亚胺）配合物反式（R*） -[PtCl 2 NH=C(R)ON=C(C9Hi6)}NH=C(R)-ON=CR 1 R 2 }] (6) 中等收率。另一种途径涉及起始配合物 1 与酮肟 3 反应得到混合亚胺-腈配合物反式-[PtCl 2 NH=C(R)ON=CR 1 R 2 }(NCR)] (5)，然后通过后者与 (R*)-樟脑肟
• Mixed unsymmetric oxadiazoline and/or imine platinum(ii) complexes
  作者：Jamal Lasri、M. Adília Januário Charmier、M. Fátima C. Guedes da Silva、Armando J. L. Pombeiro

  DOI：10.1039/b704329e

  日期：——

  Iminoacylation of acetone oxime Me2CNOH 2 upon reaction with trans-[PtCl2(NCCH2CO2Me)2] 1 and [2 + 3] cycloaddition of acyclic nitrone −O+N(Me)C(H)(C6H4Me-4) 3 to a nitrile ligand in 1 lead to the formation of mono-imine trans-[PtCl2(imine-a)(NCCH2CO2Me)] 4 [imine-a = NHC(CH2CO2Me)ONCMe2] and mono-oxadiazoline trans-[PtCl2(oxadiazoline-a)(NCCH2CO2Me)] 6 [oxadiazoline-a = NC(CH2CO2Me)ON(Me)C(H)(C6H4Me-4)] unsymmetric mixed ligand complexes, respectively, as the main products. Reactions of 6 or 4 with acetone oxime 2, cyclic nitrone −O+NCHCH2CH2CMe28 or N,N-diethylhydroxylamine 11 give access, in moderate to good yields, to the unsymmetric mixed ligand oxadiazoline and/or imine complexes trans-[PtCl2(oxadiazoline-a)(imine-a)] 9, trans-[PtCl2(oxadiazoline-a)(oxadiazoline-b)] 10 [oxadiazoline-b = NC(CH2CO2Me)ONC(H)CH2CH2CMe2], trans-[PtCl2(imine-a)(imine-b)] 12 [imine-b = NHC(CH2CO2Me)ONEt2] or trans-[PtCl2(imine-a)(oxadiazoline-b)] 13. The cis mono-imine mixed ligand complex cis-[PtCl2(imine-a)(NCCH2CO2Me)] 4a is the major product from the reaction of cis-[PtCl2(NCCH2CO2Me)2] 1a with the oxime 2, while the di-imine compound cis-[PtCl2(imine-a)2] 5a is a minor product. Reaction of cis-[PtCl2(imine-a)(NCCH2CO2Me)] 4a with N,N-diethylhydroxylamine 11 or the cyclic nitrone 8 affords, in good yields, the unsymmetric mixed ligand complexes cis-[PtCl2(imine-a)(imine-b)] 12a or cis-[PtCl2(imine-a)(oxadiazoline-b)] 13a, respectively. All these complexes were characterized by elemental analyses, IR and 1H, 13C and 195Pt NMR spectroscopies, and FAB+-MS. The X-ray structural analysis of trans-[PtCl2NHC(CH2CO2Me)ONCMe2}(NCCH2CO2Me)] 4 is also reported.

  对乙酮肟（Me2CNOH 2）与反式-[PtCl2(NCCH2CO2Me)2] 1反应后，通过与一个腈配体的[2 + 3]环加成反应，得到单亚胺化合物反式-[PtCl2(imine-a)(NCCH2CO2Me)] 4 [imine-a = NHC(CH2CO2Me)ONCMe2] 和单噁二唑啉反式-[PtCl2(oxadiazoline-a)(NCCH2CO2Me)] 6 [oxadiazoline-a = NC(CH2CO2Me)ON(Me)C(H)(C6H4Me-4)]，这两者是主要产物。化合物6或4与乙酮肟2、循环氮烯−O+NCHCH2CH2CMe28或N,N-二乙基羟胺11反应，提供了适度到良好的产率，形成不对称的混合配体噁二唑啉和/或亚胺配合物trans-[PtCl2(oxadiazoline-a)(imine-a)] 9、trans-[PtCl2(oxadiazoline-a)(oxadiazoline-b)] 10 [oxadiazoline-b = NC(CH2CO2Me)ONC(H)CH2CH2CMe2]、trans-[PtCl2(imine-a)(imine-b)] 12 [imine-b = NHC(CH2CO2Me)ONEt2]或trans-[PtCl2(imine-a)(oxadiazoline-b)] 13。由反式-[PtCl2(NCCH2CO2Me)2] 1a 与肟2反应生成的顺式单亚胺混合配体复合物cis-[PtCl2(imine-a)(NCCH2CO2Me)] 4a 是主要产物，而二亚胺化合物cis-[PtCl2(imine-a)2] 5a 是次要产物。顺式-[PtCl2(imine-a)(NCCH2CO2Me)] 4a与N,N-二乙基羟胺11或循环氮烯8反应，良好的产率分别获得不对称混合配体复合物cis-[PtCl2(imine-a)(imine-b)] 12a或cis-[PtCl2(imine-a)(oxadiazoline-b)] 13a。这些配合物通过元素分析、红外光谱、1H、13C和195Pt NMR光谱及FAB+-MS进行了表征。还报告了trans-[PtCl2NHC(CH2CO2Me)ONCMe2}(NCCH2CO2Me)] 4的X射线结构分析。
• Synthesis of Air Stable Fused Bicyclic D4-1,2,4-oxadiazoline Platinum(II) Complexes via [2+3] Cycloadditions
  作者：Jamal Lasri

  DOI：10.14233/ajchem.2015.18683

  日期：——

  The reaction of trans-[PtCl2(NCR)2] [R1 = CH2CO2Me (1a), R2 = CH2Cl (1b)] with pyrroline N-oxide −O+N=CHCH2CH2CMe2 (2) furnishes, via [2+3] cycloaddition, new fused bicyclic D4-1,2,4-oxadiazoline platinum(II) complexes trans-[PtCl2N=C(R)ONC(H)CH2CH2CMe2}2] (R1 = CH2CO2Me (3a), R2 = CH2Cl (3b)). Compounds 3a and 3b were refluxed in CH2Cl2 to afford the derived ketoimine platinum(II) complexes trans-[PtCl2N(C(=O)(R))=CCH2CH2C(Me2)NH}2] (R1 = CH2CO2Me (4a), R2 = CH2Cl (4b)), respectively, as a result of the N-O bond cleavage of the oxadiazoline ring in compound 3. All the platinum complexes were characterized by IR, 1H and 13C NMR spectroscopies, ESI+-MS and elemental analyses.

  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-[PtCl2N=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-[PtCl2N(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。
• 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
• 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.