trans-[PtCl2(NCN(CH2)5)2] | 902492-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: trans-[PtCl2(NCN(CH2)5)2]
• 英文别名: trans-[PtCl2(NCNC5H10)2]；piperidine-1-carbonitrile;platinum(2+);dichloride
• CAS: 902492-63-1
• 化学式: C₁₂H₂₀Cl₂N₄Pt
• 分子量: 486.304
• InChiKey: RVFDRIUHBSDEQI-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -4.09
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  54.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trans-[PtCl2(NCN(CH2)5)2] 在 氨 作用下， 反应 12.5h， 生成
  参考文献：
  名称：

  Guanidine platinum(II) complexes: synthesis, in vitro antitumor activity, and DNA interactions

  摘要：

  The novel guanidine compounds trans-[Pt(NH2Me)(2)(NH=C(NHMe)NR)(2)(Cl)(2) (R = NEt2 [7], NC5H10 [8]) (trans-7,8) were synthesized by the nucleophilic addition of methylamine to dialkylcyanamide ligands of the push-pull nitrile complexes trans-[PtCl2(RCN)(2)] (R=NEt2, NC5H10). In vitro cytotoxicity tests conducted for the entire series of the guanidine complexes, i.e. trans-7,8, the neutral cis- or trans-[PtCl2{NH=C(NH2)R)2} (cis-1-3 and trans-1-3) and the cationic cis- or trans-[Pt(NH3)(2){NH=C(NH2)R}(2)](Cl)(2) (cis-4-6 and trans-4-6) (R = NMe2 [1,4], NEt2 [2,5], NC5H10 [3,6]) in two human cancer cell lines, CH1 (ovarian carcinoma) and SW480 (colon cancer), confirmed that the cytotoxicity of several trans-configured (trans-3,6) complexes is higher than that of cis-congeners (cis-3,6). Cellular platinum levels were analyzed by inductively coupled plasma mass spectrometry upon treatment of SW480 cells, revealing a dependence of cellular accumulation on the geometrical isomerism and the steric hindrance of the variable substituent R on the guanidine ligand. DNA interactions of selected guanidine complexes were studied in order to find hints for the possible reasons for their different activities. Changes induced to the electrophoretic mobility of a dsDNA plasmid confirmed the potency of the guanidine complexes (e.g. trans-1,3,5,6 and cis-1,3,4) to significantly alter DNA secondary structure, indicating DNA as a possible critical target of these compounds. (C) 2013 The Authors. Published by Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2013.12.007
• 作为产物：
  描述：

  1-吡啶甲酯 以 水 为溶剂， 生成 trans-[PtCl2(NCN(CH2)5)2]
  参考文献：
  名称：

  水解金属介导的二烷基氰酰胺在Pt（IV）中心的偶联，产生新的二亚氨基配体家族。

  摘要：

  向K（2）[PtCl（4）]的水溶液中添加过量的R（2）NCN导致[PtCl（2）（NCNR（2））（2）]沉淀（R（2）= Me （2）1； Et（2）2； C（5）H（10）3； C（4）H（8）O，4）的顺/反异构体比例取决于温度。通过SiO（2）上的柱色谱分离纯净的异构体顺式1-3和反式1-3，而通过重结晶获得反式-4。固相加热至110摄氏度时，配合物顺式1-3异构化为反式1-3。通过X射线晶体学对trans-1进行了表征。氯化铂（II）配合物顺式1-3和反式1-4得到适当的铂（IV）配合物[PtCl（4）（NCNR（2））（2）]（顺式5-7和反式-5-8）。通过用纯Et（2）NCN处理[PtCl（4）（NCMe）（2）]，也可以获得化合物cis-6。在未干燥的Et（2）O和CH（2）Cl（2）的混合物中的铂（IV）络合物反式[[PtCl（4）（NCNMe（2））（2）]（tra

  DOI：

  10.1021/ic034800x

文献信息

• Facile cyanamide–ammonia coupling mediated by cis- and trans-[PtIIL2] centers and giving metal-bound guanidines
  作者：Marina R. Tyan、Nadezhda A. Bokach、Meng-Jiy Wang、Matti Haukka、Maxim L. Kuznetsov、Vadim Yu. Kukushkin

  DOI：10.1039/b806862c

  日期：——

  cis- or trans-[PtCl(2)(RCN)(2)] (R = NMe(2), NEt(2), NC(5)H(10)) at 20-25 degrees C leads to metal-mediated cyanamide-ammonia coupling to furnish, depending on reaction time, one or another type of novel bisguanidine compound, i.e. the molecular cis- or trans-[PtCl(2)NH=C(NH(2))R}(2)] (cis- and trans-) and the cationic cis- or trans-[Pt(NH(3))(2)NH=C(NH(2))R}(2)](Cl)(2) (cis- and trans-) complexes

  氨扩散到二烷基氰酰胺配合物顺式或反式[PtCl（2）（RCN）（​​2）]的CH（2）Cl（2）解决方案中（R = NMe（2），NEt（2），NC（5） ）H（10））在20-25摄氏度下导致金属介导的氰酰胺-氨偶合，从而根据反应时间而提供一种或另一种新型双胍化合物，即分子顺式或反式[PtCl（2） ）NH = C（NH（2））R}（2）]（顺式和反式）和阳离子顺式或反式-[Pt（NH（3））（2）NH = C（NH（ 2））R}（2）]（Cl）（2）（顺式和反式）配合物。因此，在NH（3）在CH（2）Cl（2）中长时间处理后，化合物顺式或反式被转换为顺式或反式。在CH（2）Cl（2）解决方案中相关腈配合物的顺式或反式[PtCl（2）（RCN）（​​2）]（R = Et，CH（2）Ph，Ph）的氨化仅提供阳离子化合物顺式或反式-[Pt（NH（3））（2）NH = C（NH（2））R
• Pt^II-Mediated 1,3-Dipolar Cycloaddition of Oxazoline <i>N</i>-Oxides to Nitriles as a Key Step to Dihydrooxazolo-1,2,4-oxadiazoles
  作者：Anastassiya V. Makarycheva-Mikhailova、Julia A. Golenetskaya、Nadezhda A. Bokach、Irina A. Balova、Matti Haukka、Vadim Yu. Kukushkin

  DOI：10.1021/ic701133b

  日期：2007.10.1

  and 13C1H} NMR spectroscopies, and X-ray diffraction (for 1, 2, 5, and 9). With the exception of benzonitrile complexes, 1,3-DCA of oxazoline N-oxides to the PtII-ligated nitriles occurred diastereoselectively and afforded mixtures of enantiomers. Depending on the substituents on nitriles, asymmetric atoms in both of the formed heterocyclic ligands have the same (SS/RR) or different (SR/RS) configurations

  通过分子间PtII生成了一种新型的杂环，即2,3a-二取代的5,6-二氢-3aH- [1,3]恶唑并[3,2-b] [1,2,4]恶二唑恶唑啉N-氧化物C（Me）2CH2OC（R）= N +（O-）（R = Me，Et）和配合物中的配位腈之间的介导的1,3-偶极环加成（1,3-DCA）顺式-[PtCl2（R'CN）2] [R'= Me，Et，CH2Ph，Ph，N（C5H10）]。对于游离的RCN和恶唑啉N-氧化物，该反应是未知的，但是在PtII介导的条件下，反应平稳进行（CH2Cl2，20-25摄氏度，18-20h），得到纯络合物[PtCl2 N = C（R' ）ONC（R）OCH2CMe2} 2] [R / R'= Me / Me，1; Me / Et，2；Me / CH2Ph，3；我/ Ph，4；Me / N（ ），5；Et / Me，6；Et / Et，7；Et / CH2Ph，8；Et
• Platinum(II)-Complexed Tetrahydroimidazo[1,2-<i>b</i>][1,2,4]oxadiazoles Derived from Metal-Mediated 1,3-Dipolar Cycloaddition. Novel Type of Heterocycles, Which Do Not Exist without the Metal Center
  作者：Nadezhda A. Bokach、Maxim L. Kuznetsov、Matti Haukka、Victor I. Ovcharenko、Eugeny V. Tretyakov、Vadim Yu. Kukushkin

  DOI：10.1021/om800963d

  日期：2009.3.9

  coordinated nitriles in the complexes cis- and trans-[PtCl2(RCN)2] (R = NMe2, NC5H10, Et). The reaction proceeds smoothly under mild conditions (CH2Cl2, 20−25 °C, 0.5−3 h) and gives the complexes [PtCl2N═C(R)ONC(R′)NHCMe2CMe2}2] (R/R′ = NMe2/Me, cis- and trans-1; NMe2/H, cis- and trans-2; R/R′ = N(C5H10)/Me, cis- and trans-3; N(C5H10)/H, cis- and trans-4; Et/H, cis- and trans-5) in 50−84% yields. These

  一种新型的杂环配体，即2- R -3a-R'-5,5,6,6-四甲基-3a，4,5,6-四氢咪唑[1,2- b ] [1,2， 4]恶二唑是由分子间Pt II介导的咪唑啉N-氧化物O NC（R'）NH CMe 2 CMe 2（R'= H，Me）与配位腈之间的分子间介导的1,3-偶极环加成反应生成的。顺式和反式[PtCl 2（RCN）2 ]复合体（R = NMe 2，NC 5 H 10，Et）。反应在温和的条件下（CH 2 Cl 2，20-25°C，0.5-3 h），得到络合物[PtCl 2 N═C（R）O NC（R'）NH CMe 2 CMe 2 } 2 ]（R / R'= NMe 2 / Me ，顺式和反式1； NMe 2 / H，顺式和反式2； R / R'= N（C 5 H 10）/ Me，顺式和反式3； N（C 5 H 10）/ H，顺式和反式4； Et / H，顺式和反式5）
• Push-Pull Nitrile Ligands Exhibit Specific Hydration Patterns
  作者：Tatyana B. Anisimova、Nadezhda A. Bokach、Konstantin V. Luzyanin、Matti Haukka、Vadim Yu. Kukushkin

  DOI：10.1039/c0dt00711k

  日期：——

  precipitated as 4·[A]2 (A = pic, 4·[pic]2; PF6, 4·[PF6]2; BPh4, 4·[BPh4]2·(NH2CONMe2)) by addition of picric acid, NaPF6, or NaBPh4, respectively, to the filtrate obtained after separation of 4·[PtCl3(Me2SO)]2·(H2O)2. In 2, the dialkylcyanamide ligand undergoes bond cleavage giving the known trans-[PtCl2N(H)C4H8O}(Me2SO)] (trans-7). All complexes were characterized by elemental analyses (C, H, N), high resolution

  之间的反应 钾[PTCl 3（Me 2 S O）]或在这项工作中制备的顺式-和反式- [氯铂酸2（NCNR 2）（ME 2小号O）]（R 2 =我2， 1 ; C ^ 4 ħ 8 O，2 ;Ç 5 ħ 10 3）与过量的的NCNR 2 in水给出了阳离子bischelate [PT κ 2 - Ñ，Ñ ''' - NH C（NME 2）OC（NME 2）NH} 2 ] 2+（4 2+）和monochelates [氯铂酸κ 2 -N， O形NH C（NR 2）NC（NR 2）Ô}（ME 2小号O）]（R 2 = C 4 H ^ 8 O，5 ;ç 5 ħ 10，6）。从反应混合物中以4的形式释放出络合物4 2+·[氯铂酸3（ME 2小号O）] 2 ·（H 2 O）2或它被沉淀为4 ·[A] 2（A = PIC，4 ·[图] 2 ; PF 6，4 ·[PF 6 ] 2 ;BPh 4，4 ·[BPh
• Platinum(II)‐Mediated Double Coupling of 2,3‐Diphenylmaleimidine with Nitrile Functionalities To Give Annulated Pentaazanonatetraenate (PANT) Systems
  作者：Daniil M. Ivanov、Pavel V. Gushchin、Alexander S. Novikov、Margarita S. Avdontceva、Andrey A. Zolotarev、Galina L. Starova、Yi‐Ting Chen、Shih‐Hung Liu、Pi‐Tai Chou、Vadim Yu. Kukushkin

  DOI：10.1002/ejic.201501398

  日期：2016.4

  Et 1, nPr 2, tBu 3, CH2Ph 4, Ph 5, p-CF3C6H4 6, NMe2 7, NEt2 8, N(CH2)5 9] with 2.5 equiv. of 2,3-diphenylmaleimidine in CH2Cl2 at room temperature for 5 min [for R = p-CF3C6H4 6, NMe2 7, NEt2 8, N(CH2)5 9] or 14 h (for R = Et 1, nPr 2, tBu 3, CH2Ph 4, Ph 5) furnishes (1,3,5,7,9-pentaazanona-1,3,6,8-tetraenato)platinum(II) [(PANT)PtII; PtClHN=C(R)N=CN[C(Ph)=C(Ph)]C=NC(R)=NH}] complexes 10–18. These

  用 2.5 当量处理反式-[PtCl2(NCR)2] [R = Et 1, nPr 2, tBu 3, Ph 4, Ph 5, p-CF3C6H4 6, NMe2 7, NEt2 8, N(CH2)5 9] . 2,3-二苯基马来酰亚胺在 Cl2 中室温 5 分钟 [对于 R = p-CF3C6H4 6、NMe2 7、NEt2 8、N( )5 9] 或 14 小时（对于 R = Et 1、nPr 2、tBu 3、 Ph 4、Ph 5)提供(1,3,5,7,9-pentaazanona-1,3,6,8-tetraenato)铂(II)[(PANT)PtII；PtClHN=C(R)N=CN[C(Ph)=C(Ph)]C=NC(R)=NH}] 络合物 10-18。这些物质是由铂 (II) 介导的 2,3-二苯基马来酰亚胺与两个腈配体的双偶联形成的。配合物的配方得到了令人满意的