cis-[PtCl2(NHC(NH2)NC5H10)2] | 1082055-75-1

• 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: cis-[PtCl2(NHC(NH2)NC5H10)2]
• 英文别名: piperidine-1-carboximidamide;platinum(2+);dichloride
• CAS: 1082055-75-1；1080652-14-7
• 化学式: C₁₂H₂₆Cl₂N₆Pt
• 分子量: 520.365
• InChiKey: HIDPFZTVEICCSL-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -5.26
• 重原子数：
  21
• 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：
  106
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-[PtCl2(NHC(NH2)NC5H10)2] 、 甲胺 反应 12.0h， 生成 trans-[Pt(NH₂Me)₂{NH = C(NHMe)N(C₅H₁₀)}₂]Cl₂
  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：

  trans-[PtCl2(NCN(CH2)5)2] 在 氨 作用下， 反应 0.5h， 生成 cis-[PtCl2(NHC(NH2)NC5H10)2]
  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

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